Name: 61-19-8|((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate|97%
Brand: Ambeed
SKU: A182461
Price: 5.0 USD
Availability: InStock
Rating: 99 (29 reviews)

1
[ 60-92-4 ]
[ 84-21-9 ]
[ 61-19-8 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1992,p. 1707 - 1708
[2]Australian Journal of Chemistry,1992,vol. 45,p. 1187 - 1190
[3]Journal of the Chemical Society. Perkin transactions II,1994,p. 309 - 314
[4]Journal of the Chemical Society. Chemical communications,1994,p. 1755 - 1756
[5]Journal of the Chemical Society. Perkin Transactions 2 (2001),1997,p. 75 - 78
[6]Journal of the American Chemical Society,1959,vol. 81,p. 6198,6200

2
[ 488-69-7 ]
[ 61-19-8 ]
[ 56-65-5 ]

Reference： [1]Biochemische Zeitschrift,1936,vol. 283,p. 114,117

3
[ 67-07-2 ]
[ 61-19-8 ]
[ 56-65-5 ]

Reference： [1]Biochimica et Biophysica Acta,1960,vol. 39,p. 82,85
Biochemical Preparations,1962,vol. 9,p. 120,123

4
[ 61-19-8 ]
[ 56-65-5 ]
[ 58-64-0 ]

Reference： [1]Methods in Enzymology,1955,vol. 2,p. 598
[2]Journal of Biological Chemistry,1960,vol. 235,p. 3260,3262
[3]Phytochemistry,1996,vol. 42,p. 589 - 594
[4]Journal of the American Chemical Society,2012,vol. 134,p. 16562 - 16570,9

5
[ 61-19-8 ]
[ 58-64-0 ]
[ 56-65-5 ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 4801 - 4804
[2]Chemistry Letters,1985,p. 985 - 988
[3]Chemistry Letters,1985,p. 985 - 988
[4]Journal of the American Chemical Society,1954,vol. 76,p. 3517,3521
[5]Tetrahedron Letters,1982,vol. 23,p. 5415 - 5418
[6]Journal of the American Chemical Society,1954,vol. 76,p. 3517,3521
[7]Antimicrobial Agents and Chemotherapy,1995,vol. 39,p. 2304 - 2308
[8]RSC Advances,2014,vol. 4,p. 2103 - 2108
[9]Patent: US2795580,1955,
[10]ChemBioChem,2019,vol. 20,p. 2961 - 2967

6
[ 61-19-8 ]
[ 56-65-5 ]

Reference： [1]Journal of the Chemical Society,1956,p. 1371,1375
[2]Biochemical Preparations,1961,vol. 8,p. 1
[3]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 4303 - 4313
[4]Russian Journal of Bioorganic Chemistry,2009,vol. 35,p. 734 - 738
[5]ChemBioChem,2019,vol. 20,p. 2961 - 2967
[6]ChemCatChem,2020,vol. 12,p. 1184 - 1189

7
[ 61-19-8 ]
[ 58-61-7 ]

Yield	Reaction Conditions	Operation in experiment
	With water at 30℃; for 0.166667h; relative rate, different alkaline phosphotases;
	With phosphatase Phosphatase-Praeparat aus Kaninchen-Niere;
	With phosphatase Phosphatase-Praeparat aus Knochen;

	Behandlung mit Enzym-Praeparaten aus verschiedenen pflanzlichen Geweben;
	With acetonedryyeast; water
	With mono-p-nitrophenyl phosphate; D-Sorbose; 2-amino-ethanol hydrochloride; magnesium chloride In water at 25℃; for 0.0833333h;
	With Escherichia coli 5'-nucleotidase; potassium chloride; calcium chloride; cobalt(II) chloride; bovine serum albumin In aq. buffer at 20℃; for 0.333333h; Enzymatic reaction;	2.4. Enzyme kinetics General procedure: The reaction buffer used for determination of the specific activity consisted of 20 mM BisTris (pH 7.0), 50 mM KCl and 20 mM CaCl2. CoCl2 was added to a concentration of 5 mM shortly before starting the reaction. The 5NT protein samples were diluted in reaction buffer supplemented with 50 μg/ml BSA to prevent adhesion to the reaction tubes and with 5 mM CoCl2. The reactions were started at room temperature by addition of 180 μl of reaction buffer containing the respective concentration of substrate to 20 μl of protein sample. Released phosphate was detected according to a modified malachite green assay [10,11]. The reaction was restricted to 10% phosphate release. After 20 min of color development the samples were measured at a Tecan-Sunrise Microplate Reader (Crailsheim/Germany) at a wavelength of 620 nm. Experimental data were fitted according to Michaelis-Menten using OriginPro 8G. It should be pointed out that the substrate concentrations used here were partly not sufficient to reach the saturation plateau. Due to an increased autohydrolysis of the substrates it was not possible to use higher substrate concentrations in the malachite green assay. With the assumption that the AMP concentration was much smaller than the Km-value the specificity constant of 5NT-NDom with AMP was calculated from the slope of the curve shown in Fig. 4B.
	With alkaline phosphatase Enzymatic reaction;
	With Acinetobacter baumannii recombinant acid phosphatase; nickel dichloride; bovine serum albumin In water Cooling with ice; Enzymatic reaction;	Acid phosphatase assay General procedure: Unless indicated otherwise, reaction mixtures contained 2.0 mM PNPP (Sigma Chemical Co.)or phosphorylated compounds (Sigma Chemical Co.), 0.20MMES (Sigma Chemical Co.)buffer, pH 6.0, 2.0 mM NiCl2, and 0.080-0.30 μg total Acinetobacter baumannii rAcpA protein,and were brought to a final concentration of 0.186 μg/μL protein with addition of bovineserum albumin (BSA, BioRad Laboratories) in a total reaction volume of 200 μL (determinationof released phosphate) or 300 μL (determination of released paranitrophenol). All incubationswere carried out for 30 minutes at 37 °C after which time reactions were placed in an iceslurry for 3 minutes followed by addition of enzyme to the respective blanks and reactionswere terminated by heating at 65 °C for 10 minutes followed by immersion in an ice slurry for3 minutes. Released phosphate was determined by addition of 1.0 mL BIOMOL GREEN phosphatereagent (Enzo Life Sciences), and monitored at 620 nm using a Genesys 10 UV ScanningSpectrophotometer (Thermo Scientific). Paranitrophenol was monitored at 405 nm followingaddition of 1.7 mL 0.5MGlycine buffer, pH 10. Following subtraction of blank values, paranitrophenoland released phosphate were quantitated using paranitrophenol and phosphatestandard curves, respectively. All reactions, i.e., generation of paranitrophenol and release offree phosphate were linear with both time (30 minutes) and assay protein (0.30 μg, ~ 13.2 nM).Specific activity is expressed as nmoles paranitrophenol or free phosphate liberated mg-1s-1.

Reference： [1]Sakurai, Yonekichi; Toda, Katsuyoshi; Shiota, Hideo [Agricultural and Biological Chemistry, 1981, vol. 45, # 9, p. 1959 - 1968]
[2]Carter [Journal of the American Chemical Society, 1950, vol. 72, p. 1466,1469]
[3]Gulland; Holiday [Journal of the Chemical Society, 1936, p. 765,766,768]
[4]Bargoni; Luzzati [Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1956, vol. <8>21, p. 450]
[5]Ostern et al. [Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1938, vol. 255, p. 104,114,117]
[6]Ishida, Yoshihiro; Tsuruta, Hiroki; Tsuneta, Sofia T.; Uno, Tomohide; Watanabe, Keiichi; Aizono, Yasuo [Bioscience, Biotechnology and Biochemistry, 1998, vol. 62, # 11, p. 2246 - 2250]
[7]Krug, Ulrike; Patzschke, Rica; Zebisch, Matthias; Balbach, Jochen; Sträter, Norbert [FEBS Letters, 2013, vol. 587, # 5, p. 460 - 466]
[8]Xing, Xiaojing; Liu, Xueguo; Zhou, Ying; Xu, Dangdang; Pang, Daiwen; Tang, Hongwu [RSC Advances, 2016, vol. 6, # 14, p. 11815 - 11821]
[9]Smiley-Moreno, Elizabeth; Smith, Douglas; Yu, Jieh-Juen; Cao, Phuong; Arulanandam, Bernard P.; Chambers, James P. [PLoS ONE, 2021, vol. 16, # 6 June]

8
[ 64-19-7 ]
[ 56-65-5 ]
[ 61-19-8 ]

Reference： [1]Biochemische Zeitschrift,1932,vol. 254,p. 381,386,393

9
[ 56-65-5 ]
[ 61-19-8 ]

Yield	Reaction Conditions	Operation in experiment
	With pyruvate kinase; myokinase; Escherichia coli acetyl-CoA synthetase; coenzyme A; NADH; magnesium chloride; Cleland's reagent; lactate dehydrogenase; In aq. phosphate buffer; at 37℃;pH 7.5;Enzymatic reaction;Kinetics;	The acetyl-CoA synthetase assay was based on the coupled assayreported by Williamson and Corkey [33]. AMP production was detectedvia a coupled enzyme assay in which myokinase (MK), pyruvate kinase(PK) and lactate dehydrogenase (LDH) couple AMP production toNADH oxidation. Standard acetyl-CoA synthetase assays (0.2 mL) wereperformed at 37 C in 50mM potassium phosphate buffer at pH 7.5containing 3.0mM PEP (phosphoenolpyruvate), 5 units MK, 1 unit PK,1.5 units LDH, 5mM MgCl2, 2.5mM <strong>[56-65-5]ATP</strong>, 1.5mM CoA, 0.1mM NADH,5mM acetate and 1mM DTT. The reaction was started by the additionof Acs. All reactions were performed in triplicate. Specific activity wascalculated using the extinction coefficient of NADH (6.22mM-1 cm-1)and was based on the oxidation of two molecules of NADH for eachAMP molecule released. One unit of Acs activity is defined as 1 mumole ofacetyl-CoA formed per minute at pH 7.5 and 37 C. Obtained milliunitsof absorbance per minute at 340 nm (Synergy H1 Hybrid Multi-ModeReader, Biotek), were converted to units of absorbance per minute bymeans of the PathCheck Sensor feature. Substrate concentrations werevaried from 0 to 0.5mM for <strong>[56-65-5]ATP</strong> and 0 to 2mM for acetate. Pseudofirst-order kinetic parameters were determined using Prism v6(GraphPad) analytical software and standard deviations were determinedfrom the three replicates. Statistical multiple comparison onewayANOVA has been carried out for kinetic parameters to know if thedifferences between parameters were or not significatively different.Acs inhibition assays were carried out employing a pyrophosphate detectionkit (Sigma Aldrich) following the commercial protocol.

Reference： [1]Journal of the American Chemical Society,1959,vol. 81,p. 6075,6198,6202
[2]Zhurnal Obshchei Khimii,1959,vol. 29,p. 215,219;engl.Ausg.S.218,222
[3]Biochemische Zeitschrift,1932,vol. 253,p. 395,406
[4]Journal of Biological Chemistry,1947,vol. 167,p. 445,449
[5]ACH - Models in Chemistry,1996,vol. 133,p. 365 - 388
[6]Chemical Communications,2008,p. 4034 - 4036
[7]Organic and Biomolecular Chemistry,2010,vol. 8,p. 1033 - 1039
[8]Journal of Biological Chemistry,2011,vol. 286,p. 40867 - 40877
[9]Journal of Coordination Chemistry,2011,vol. 64,p. 3441 - 3453
[10]Chemical Communications,2014,vol. 50,p. 12037 - 12039
[11]Biochimica et Biophysica Acta - General Subjects,2019,vol. 1863,p. 1040 - 1049
[12]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2020,vol. 225

10
[ 58-61-7 ]
[ 61-19-8 ]
[ 56-65-5 ]

Reference： [1]Patent: US2606899,1948,
[2]Patent: US2606899,1948,
[3]Patent: US2606899,1948,
[4]Patent: DE703400,1939,
[5]Patent: DE703400,1939,
[6]Patent: DE703400,1939,

11
[ 114-33-0 ]
[ 61-19-8 ]
Phosphoric acid mono-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester; compound with N-methyl-nicotinamide [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1983,vol. 113,p. 111 - 114

12
[ 606-67-7 ]
[ 61-19-8 ]
[ 58-64-0 ]

Reference： [1]Journal of the American Chemical Society,1985,vol. 107,p. 8288 - 8289
[2]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2278 - 2284

13
C₄₉H₆₂N₂₀O₃₁P₄ [ No CAS ]
[ 63-37-6 ]
[ 365-07-1 ]
[ 61-19-8 ]
[ 85-32-5 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 2611 - 2614

14
C₅₁H₆₇N₂₁O₃₄P₅^(1-) [ No CAS ]
[ 6216-59-7 ]
[ 63-37-6 ]
[ 365-07-1 ]
[ 61-19-8 ]
[ 85-32-5 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 2611 - 2614

15
[ 288-32-4 ]
[ 61-19-8 ]
[ 60031-83-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 1H-imidazole; 5'-adenosine monophosphate With 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine In dimethyl sulfoxide; N,N-dimethyl-formamide for 3h; Stage #2: With sodium perchlorate; triethylamine In diethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone for 2h;
	With 2,2'-dipyridyldisulphide; triphenylphosphine; sodium iodide In dimethyl sulfoxide for 0.666667h; Ambient temperature;
	Stage #1: 1H-imidazole; 5'-adenosine monophosphate With 2,2'-dipyridyldisulphide; tributyl-amine; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: With sodium perchlorate In N,N-dimethyl-formamide; acetone	6 Adenosine-5'-monophosphate (6 mmol) was dissolved in 1:1 mixture of methanol and water (100 mL) and the resulting solution was treated with tri-n-butylamine (7.2 mL, 30 mmol). The solution was evaporated to dryness. The residue was dissolved in methanol and re-evaporated twice. Subsequently, this procedure was repeated twice with anhydrous DMF (50 mL) using an oil pump. The residue was dissolved in 30 mL of anhydrous DMF and then imidazole (4.1 g, 60 mmol), 2,2'-dithiopyridine (10.6 g, 48 mmol) and triphenylphosphine (12.6 g, 48 mmol) were added. The solution was stirred for 2 hours at room temperature. It was then treated with 10 mL of 1 M sodium perchlorate solution in acetone (30 mL). The sodium salt of adenosine-5'-phosphoroimidazolate was obtained as a white precipitate, which was collected by centrifugation, washed with acetone (5*30 mL), and then dried in a desiccator. The product (2.25 g, 5.3 mmol, 88%) was used in the next step without further purification.

	Stage #1: 1H-imidazole; 5'-adenosine monophosphate With 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine In dimethyl sulfoxide; N,N-dimethyl-formamide Stage #2: With sodium perchlorate; triethylamine In diethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone for 2h;
	Stage #1: 1H-imidazole; 5'-adenosine monophosphate With 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine In dimethyl sulfoxide; N,N-dimethyl-formamide for 2h; Stage #2: With sodium perchlorate; triethylamine In diethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone for 0.5h;	2.3. Preparation of the activated nucleotides General procedure: A mixture of a mononucleotide (AMP or UMP, 1.76mmol) and imidazole (22mmol) was added to DMF (10mL) in a 50-mL flask and the solvent was evaporated to dryness at reduced pressure. The evaporation was repeated twice with DMF (2×10mL) to remove residual water. The residue was dissolved in a mixture of DMF (10mL) with DMSO (10mL) and stirred with 2,2′-dithiodipyridine (6.5mmol), triphenylphosphine (6.36mmol), and TEA (6.5mmol) for 2h. The resulting product was recovered from the clear yellow reaction mixture as a precipitate by adding the reaction mixture drop wise to a solution of anhydrous NaClO4 (3.5g) in a mixture of ether (100mL), acetone (100mL) and TEA (20mL) with stirring. The stirring was continued for 30min (to ensure complete formation of the Na+ salt) and a colorless, flocculent solid was precipitated which was allowed to settle (30min). The supernatant is decanted and the remaining reaction mixture was centrifuged. The resulting colorless pellet was washed twice with a mixture of ether (100mL) and acetone (100mL) and then with ether (100mL) and dried overnight in a vacuum desiccator. The purity of ImpA and ImpU as determined by reverse phase HPLC was >99.5%.

Reference： [1]Location in patent: experimental part Joshi, Prakash C.; Aldersley, Michael F.; Zagorevskii, Dmitri V.; Ferris, James P. [Nucleosides, nucleotides and nucleic acids, 2012, vol. 31, # 7, p. 536 - 566]
[2]Imai, Jiro; Torrence, Paul F. [Journal of Organic Chemistry, 1985, vol. 50, # 9, p. 1418 - 1426]
[3]Current Patent Assignee: TEVA PHARMACEUTICAL INDUSTRIES LTD. - US2011/237529, 2011, A1 Location in patent: Page/Page column 31
[4]Location in patent: experimental part Joshi, Prakash C.; Aldersley, Michael F.; Ferris, James P. [Biochemical and Biophysical Research Communications, 2011, vol. 413, # 4, p. 594 - 598]
[5]Joshi, Prakash C.; Dubey, Krishna; Aldersley, Michael F.; Sausville, Meaghen [Biochemical and Biophysical Research Communications, 2015, vol. 462, # 2, p. 99 - 104]

16
[ 4975-73-9 ]
[ 61-19-8 ]
[ 68134-83-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 3186 - 3195

17
[ 1094-61-7 ]
[ 61-19-8 ]
C₁₁H₁₅N₂O₈P*C₁₀H₁₄N₅O₇P [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1983,vol. 113,p. 111 - 114

18
[ 61-19-8 ]
[ 131-99-7 ]
[ 58-64-0 ]
[ 56-65-5 ]

Reference： [1]Agricultural and Biological Chemistry,1988,vol. 52,p. 909 - 914
[2]Agricultural and Biological Chemistry,1988,vol. 52,p. 909 - 914
[3]Agricultural and Biological Chemistry,1988,vol. 52,p. 909 - 914
[4]Agricultural and Biological Chemistry,1988,vol. 52,p. 909 - 914

19
[ 61-19-8 ]
[ 58-64-0 ]
[ 56-65-5 ]
[ 1062-98-2 ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 4801 - 4804
[2]Tetrahedron Letters,1993,vol. 34,p. 4801 - 4804

20
[ 58-64-0 ]
[ 61-19-8 ]

Yield	Reaction Conditions	Operation in experiment
	With nucleoside triphosphate diphosphohydrolase from Legionella pneumophila; In aq. buffer; at 37 - 99℃; for 0.25h;Enzymatic reaction;Kinetics;	The reaction mixture for the Lp1NTPDase inhibition assay contained 50 lL ADP (final concentration 500 lM) dissolved in assay buffer, 10 lL of test compound, and 30 lL of enzyme buffer in a reaction tube. The enzymatic reaction was initiated by adding 10 lL of enzyme solution to each test tube, carried out at 37Cfor 10 min and stopped by heating at 99C for 5 min. Then 100 lL of internal standard UMP (40 lM or 50lM) was added, 100 lL of the resulting solution was transferred to a CE vial and subjected to the CE.
	With SmNPP5;Enzymatic reaction;	SmNPP5 has additional promiscuity and has been shown to cleave substrates in addition to ADP. As a non-limiting example, SmNPP5 has been shown to cleave Ap3A (diadenosine triphosphate) into AMP and Pi (see e.g., FIG. 9A-FIG. 9C). As another non limiting example, SmNPP5 has been shown to cleave Ap4A (diadenosine tetraphosphate) into AMP and PPi (see e.g., FIG. 10A-FIG. 10C). Ap3A and Ap4A are both canonical ATPase inhibitors. Without wishing to be bound by theory, it is proposed that cleavage of Ap3 A or Ap4A by SmNPP5 can have an effect on coagulation, such as an anti-coagulation effect.

Reference： [1]Chemical and Pharmaceutical Bulletin,1982,vol. 30,p. 2926 - 2934
[2]Helvetica Chimica Acta,1983,vol. 66,p. 2454 - 2466
[3]Biochemical Pharmacology,2004,vol. 67,p. 1917 - 1926
[4]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4363 - 4371
[5]Patent: WO2019/178526,2019,A1 .Location in patent: Paragraph 00196

21
[ 58-64-0 ]
[ 61-19-8 ]
[ 56-65-5 ]

Reference： [1]Chemistry Letters,1985,p. 985 - 988
[2]Chemistry Letters,1985,p. 985 - 988
[3]Chemistry Letters,1985,p. 985 - 988
[4]Journal of the American Chemical Society,1986,vol. 108,p. 169 - 173
[5]Phytochemistry,1996,vol. 42,p. 589 - 594

22
[ 60-18-4 ]
[ 56-65-5 ]
[ 61-19-8 ]

Reference： [1]Tetrahedron,1984,vol. 40,p. 113 - 117

23
[ 56-65-5 ]
[ 61-19-8 ]
[ 58-64-0 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1982,vol. 30,p. 2926 - 2934
[2]Bulletin of the Chemical Society of Japan,1996,vol. 69,p. 765 - 774
[3]ACH - Models in Chemistry,1996,vol. 133,p. 365 - 388
[4]Biochemical Pharmacology,2004,vol. 67,p. 1917 - 1926
[5]Inorganic Chemistry,2016,vol. 55,p. 4864 - 4873

24
[ 56-65-5 ]
[ 61-19-8 ]
[ 5959-90-0 ]
[ 5542-28-9 ]
[ 58-64-0 ]

Reference： [1]Agricultural and Biological Chemistry,1989,vol. 53,p. 615 - 624

25
[ 1121-58-0 ]
[ 61-19-8 ]
adenosine 5'-phosphoro-4-(methylamino)pyridinium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine In dimethyl sulfoxide; N,N-dimethyl-formamide for 2h; Yield given;

Reference： [1]Prabahar, K. Joseph; Cole, Timothy D.; Ferris, James P. [Journal of the American Chemical Society, 1994, vol. 116, # 24, p. 10914 - 10920]

26
A(2'p5'G)3'p5'C [ No CAS ]
[ 63-37-6 ]
[ 61-19-8 ]
[ 85-32-5 ]

Reference： [1]Tetrahedron,1995,vol. 51,p. 9899 - 9916

27
A(2'p5'A)3'p5'C [ No CAS ]
[ 63-37-6 ]
[ 61-19-8 ]

Reference： [1]Tetrahedron,1995,vol. 51,p. 9899 - 9916

28
[ 636-70-4 ]
[ 61-19-8 ]
[ 175027-18-6 ]
P¹-<1,2-O-isopropylidene-3(R)-(nicotinamid-6-ylmethyl)-α-D-ribofuranos-5-yl>-P²-(adenosin-5'-yl)pyrophosphate [ No CAS ]

Reference： [1]Nucleosides and Nucleotides,1996,vol. 15,p. 149 - 167

29
[ 60-92-4 ]
[ 84-21-9 ]
[ 61-19-8 ]
[ 58-61-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1996,vol. 35,p. 1144 - 1147
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1996,vol. 35,p. 1144 - 1147

30
[ 5142-23-4 ]
[ 61-19-8 ]
adenosine 5'-phosphoro-3-methyladeninium [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 4330 - 4337

31
[ 56-65-5 ]
[ 61-19-8 ]
[ 66224-66-6 ]
[ 58-64-0 ]
[ 58-61-7 ]

Reference： [1]Chemistry Letters,1999,p. 125 - 126

32
[ 56-65-5 ]
[ 58-61-7 ]
adenosine kinase [ No CAS ]
[ 61-19-8 ]

Reference： [1]Journal of Biological Chemistry,1951,vol. 193,p. 481,487,489

33
[ 56-65-5 ]
aqueous Ba(OH)2 [ No CAS ]
[ 61-19-8 ]

Reference： [1]Biochemische Zeitschrift,1956,vol. 328,p. 44,48, 50

34
[ 56-65-5 ]
aqueous NaOH [ No CAS ]
[ 61-19-8 ]

Reference： [1]Biochemische Zeitschrift,1956,vol. 328,p. 44,48, 50

35
[ 56-65-5 ]
nucleotide pyrophosphatase [ No CAS ]
[ 61-19-8 ]

Reference： [1]Biochemist's Handbook <London 1961> S. 254,

36
[ 61-19-8 ]
[ 56-65-5 ]
adenylate-kinase [ No CAS ]
[ 58-64-0 ]

Reference： [1]Methods in Enzymology,1955,vol. 2,p. 598

37
[ 7732-18-5 ]
[ 56-65-5 ]
[ 61-19-8 ]
[ 58-64-0 ]

Reference： [1]Bulletin de la Societe de chimie biologique,1958,vol. 40,p. 759 - 765
[2]Bulletin de la Societe de chimie biologique,1958,vol. 40,p. 759 - 765
[3]Bulletin de la Societe de chimie biologique,1958,vol. 40,p. 759 - 765
[4]Bulletin de la Societe de chimie biologique,1958,vol. 40,p. 759 - 765

38
[ 56-65-5 ]
[ 58-61-7 ]
adenosine-kinase [ No CAS ]
[ 61-19-8 ]
[ 58-64-0 ]

Reference： [1]The Enzymes, Bd. 6 <New York 1962> S. 133,

39
[ 58-61-7 ]
phosphate [ No CAS ]
brewer's yeast-substances [ No CAS ]
[ 61-19-8 ]
[ 56-65-5 ]

Reference： [1]Patent: US2700038,1955,
[2]Patent: DE703400,1939,

40
[ 488-69-7 ]
[ 58-61-7 ]
phosphate [ No CAS ]
brewer's yeast-substances [ No CAS ]
[ 61-19-8 ]
[ 56-65-5 ]

Reference： [1]Patent: US2700038,1955,
[2]Patent: DE703400,1939,

41
[ 7732-18-5 ]
[ 56-65-5 ]
[ 61-19-8 ]
[ 58-61-7 ]

Reference： [1]Journal of the American Chemical Society,1950,vol. 72,p. 1835

42
[ 61-19-8 ]
5,7-Dimethoxycoumarin radical cation [ No CAS ]
[ 487-06-9 ]
[ 61-19-8 ]

Reference： [1]Photochemistry and Photobiology,2000,vol. 72,p. 155 - 162

43
[ 56-65-5 ]
[ 61-19-8 ]
[ 58-64-0 ]
[ 58-61-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 1805 - 1811

44
[ 56-65-5 ]
[ 61-19-8 ]
[ 66224-66-6 ]
[ 58-61-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 1805 - 1811

45
[ 5959-90-0 ]
[ 60-92-4 ]
[ 61-19-8 ]
[ 58-64-0 ]
C₂₀H₂₉N₁₀O₁₇P₃ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 770 - 776

46
[ 5542-28-9 ]
[ 61-19-8 ]
[ 58-64-0 ]
[ 56-65-5 ]
C₁₅H₂₅N₅O₂₀P₄ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 770 - 776

47
[ 37839-81-9 ]
[ 61-19-8 ]

Reference： [1]Journal of Chemical Thermodynamics,2003,vol. 35,p. 1809 - 1830

48
[ 60-92-4 ]
[ 61-19-8 ]

Yield	Reaction Conditions	Operation in experiment
	With bovine serum albumin; In aq. buffer; at 30℃;Enzymatic reaction;	General procedure: Time course experiments were performed in PDE buffer + 0.05% (m/v) BSA at a <strong>[60-92-4]cAMP</strong>- or cCMP-concentration of 3 muM. The purified GST-tagged and truncated PDE7A1/2 was added at a concentration of 0.95 mug/ml, corresponding to 210 pmol/(min ml). Crude PDE7A1-containing Sf9 cell lysate was added to yield a final activity of 5 U/ml. The samples were incubated at 30 C under constant shaking. Aliquots were drawn at appropriate times, processed as described for the enzyme screening experiments (Section 2.2) and analyzed by HPLC-MS/MS as described in the Supplementary Methods. In all experiments, the samples were repeatedly subjected to short centrifugations (at least every 30 min) to avoid concentration changes by evaporation- and condensation processes.
	With ethylenediaminetetraacetic acid; recombinant N-terminally GST-tagged human cardiac phosphodiesterase PDE3A (484?1141); magnesium chloride; BSA; In aq. buffer; at 30℃; for 0.0333333h;pH 7.5;Enzymatic reaction;Kinetics; Catalytic behavior;	General procedure: For the determination of KM and Vmax values of PDE3A mediated <strong>[60-92-4]cAMP</strong> and cUMP hydrolysis, substrate concentrations between 0.1 and 6 muM (<strong>[60-92-4]cAMP</strong>) and between 1muM and 1.5 mM (cUMP) were used in 1× PDE buffer supplemented with 0.05% of BSA. The reaction was started by adding PDE3A to yield a final concentration of 0.1mug/ml and a final sample volume of 50 mul. Negative controls without PDE were run in parallel for each substrate concentration. All samples were run in duplicates and incubated for 15 min (cUMP) or 2 min (<strong>[60-92-4]cAMP</strong>) at 30 C under constant shaking (300 rpm). After that, 40 mul aliquots were drawn, heat-inactivated, and frozen overnight as described in the section about the time course experiments. In the next step, the samples were thawed and centrifuged(15 min, 20,800×g, 4 C) to remove precipitated protein. In case of samples with less than 10 muM of cNMPs, 10mul of the supernatant was diluted 1:4 with purified water. For cNMP concentrations of more than 10muM and less than 0.5 mM, the supernatant was diluted 1:200 (1:50, followed by 1:4) with purified water. Substrate concentrations higher than 0.5 mM were diluted 1:400 (1:100, followed by 1:4). Forty microliters of these dilutions were mixed 1:1 with tenofovir solution(100 ng/ml) to yield a final tenofovir concentration of 50 ng/ml and a final volume of 80 mul. The HPLC-MS/MS measurement was performed as previously described (Monzel et al.2014).
	With rhodopsin fused to a C-terminal cyclic nucleotide phosphodiesterase domain; sodium chloride; sodium hydroxide; magnesium chloride; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid; In aq. buffer; at 20℃;pH 6.5;Irradiation; Enzymatic reaction;	General procedure: HEK293T cells were transfected with plasmid pCDNA3.1-Rh-PDE by the calcium phosphate method. DMEM/F-12medium contained 0.5 M all-trans-retinal and penicillin andstreptomycin. The cells were harvested after 24 h and washed inbufferA(140mMNaCl, 3mMMgCl2, 50mMHEPES-NaOH,pH6.5). The cells were resuspended with buffer A and homogenizedusing a Potter-Elehjem grinder (Wheaton) and a syringewith a 27-gauge needle. The syringe was filled and drained fivetimes while stirring the homogenate. The protein amount wasdetermined by a BCA protein assay (Thermo Fisher Scientific).Samples were kept in the dark before measurement for at least2 h. Catalytic activity was measured at room temperature in 100l of buffer A with 1.6-1.8 g (in the case of cGMP) or 16-18g (in the case of <strong>[60-92-4]cAMP</strong>) of total protein in a 1.5-ml sampletube. The sample was illuminated with a xenon lamp (MAX-303, Asahi Spectra Co.) through a Y52 filter (7 mW mm2).Reaction was initiated by adding cyclic nucleotides (final concentration100 M). Aliquots were taken out at different timepoints, and the reactions were immediately terminated by adding100 l of 0.1 N HCl and frozen in liquid nitrogen. Afterthawing, the samples were centrifuged to remove the membranesand denatured proteins. Nucleotides (20 l of aliquot)were separated by HPLC (Shimadzu Corp., Kyoto, Japan) with aC18 reversed-phase column (Waters) and 100 mM potassiumphosphate (pH 5.9), 4 mM tetrabutylammonium iodide, and10% (v/v) methanol as eluent (12, 26). Nucleotides were monitoredat 254 nm. Data were evaluated with LabSolutions (Shimadzu).Peak areas were integrated and assigned to the eductcyclic nucleotide based on retention times of correspondingstandard compound.

Reference： [1]Journal of Chemical Thermodynamics,2003,vol. 35,p. 1809 - 1830
[2]Bioscience, Biotechnology and Biochemistry,2009,vol. 73,p. 968 - 970
[3]Journal of Medicinal Chemistry,2009,vol. 52,p. 6546 - 6557
[4]FEBS Letters,2014,vol. 588,p. 3469 - 3474
[5]Naunyn-Schmiedeberg's Archives of Pharmacology,2017,vol. 390,p. 269 - 280
[6]Journal of Biological Chemistry,2017,vol. 292,p. 7531 - 7541

49
[ 138-08-9 ]
[ 61-19-8 ]
[ 127-17-3 ]
[ 56-65-5 ]

Reference： [1]Journal of Chemical Thermodynamics,2003,vol. 35,p. 1809 - 1830

50
[ 61-19-8 ]
[ 60-92-4 ]

Reference： [1]Journal of Chemical Thermodynamics,2003,vol. 35,p. 1809 - 1830

51
[ 127-17-3 ]
[ 56-65-5 ]
[ 138-08-9 ]
[ 61-19-8 ]

Reference： [1]Journal of Chemical Thermodynamics,2003,vol. 35,p. 1809 - 1830

52
C₁₇H₂₂N₆O₁₂P₂S [ No CAS ]
4-Methyl-5-[2-(phosphonooxy)ethyl]-1,3-thiazole-2-carboxylic acid [ No CAS ]
[ 61-19-8 ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium chloride In water at 37℃; for 2h;
	With nucleotide pyrophosphatase Enzymatic reaction;

Reference： [1]Chatterjee, Abhishek; Jurgenson, Christopher T.; Schroeder, Frank C.; Ealick, Steven E.; Begley, Tadhg P. [Journal of the American Chemical Society, 2006, vol. 128, # 22, p. 7158 - 7159]
[2]Location in patent: experimental part Hazra, Amrita; Chatterjee, Abhishek; Begley, Tadhg P. [Journal of the American Chemical Society, 2009, vol. 131, p. 3225 - 3229]

53
[ 61-19-8 ]
[ 58-64-0 ]
[ 56-65-5 ]
[ 58-61-7 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2008,vol. 27,p. 872 - 875

54
[ 4578-31-8 ]
[ 61-19-8 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 1724 - 1727
[2]Organic and Biomolecular Chemistry,2010,vol. 8,p. 4637 - 4652

55
[ 523-98-8 ]
[ 56-65-5 ]
[ 61-19-8 ]
[ 85-32-5 ]

Reference： [1]Journal of Molecular Biology,2010,vol. 395,p. 417 - 429

56
[ 34051-17-7 ]
[ 68914-00-1 ]
[ 84-21-9 ]
[ 61-19-8 ]
[ 130-49-4 ]
[ 1053-73-2 ]
[ 56-65-5 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2010,vol. 29,p. 245 - 256

57
[ 34051-17-7 ]
[ 61-19-8 ]
[ 56-65-5 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2010,vol. 29,p. 245 - 256

58
[ 58-61-7 ]
[ 68914-00-1 ]
[ 84-21-9 ]
[ 61-19-8 ]
[ 130-49-4 ]
[ 1053-73-2 ]
[ 56-65-5 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2010,vol. 29,p. 245 - 256

59
C₈₉H₁₁₂N₃₄O₆₂P₈ [ No CAS ]
C₂₀H₂₇N₇O₁₅P₂ [ No CAS ]
C₂₀H₂₇N₇O₁₆P₂ [ No CAS ]
C₃₀H₃₈N₁₂O₂₀P₂ [ No CAS ]
[ 63-37-6 ]
[ 61-19-8 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 6120 - 6126

60
[ 1094-61-7 ]
[ 15715-58-9 ]
[ 24558-92-7 ]
P₁,P₂-di(adenosin-5'-yl)diphosphate bis(triethylammonium) salt [ No CAS ]
0.2CH₂O₃*1.2C₆H₁₅N*C₂₁H₂₇N₇O₁₄P₂ [ No CAS ]
[ 61-19-8 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 6496 - 6497

61
yeast RNA [ No CAS ]
[ 63-37-6 ]
[ 58-97-9 ]
[ 61-19-8 ]
[ 85-32-5 ]

Reference： [1]Bulletin of the Chemical Society of Ethiopia,2010,vol. 24,p. 167 - 174

62
[ 2591-17-5 ]
[ 56-65-5 ]
oxyluciferin [ No CAS ]
[ 61-19-8 ]

Reference： [1]Photochemical and Photobiological Sciences,2011,vol. 10,p. 1039 - 1045

63
[ 3614-61-7 ]
[ 56-65-5 ]
[ 85-61-0 ]
[ 1380518-01-3 ]
[ 61-19-8 ]

Reference： [1]Journal of Biological Chemistry,2011,vol. 286,p. 40717 - 40724

64
[ 5542-28-9 ]
[ 61-19-8 ]
[ 56-65-5 ]

Reference： [1]Biological and Pharmaceutical Bulletin,2012,vol. 35,p. 1191 - 1196

65
[ 56-65-5 ]
[ 61-19-8 ]
[ 19375-33-8 ]

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 1464 - 1466

66
[ 61-68-7 ]
[ 61-19-8 ]
[ 1425793-56-1 ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-carbodiimide; In pyridine; water; at 4℃; for 7h;	The synthesis of MFA-AMP, MFA-Gly, MFA-NAC, and MFA-Tau wascarried out with a solution consisting of 110 mg N,N9-dicyclohexylcarbodiimidein 0.4 ml pyridine (Ikegawa et al., 1999; Horng and Benet, 2013). Briefly, an N,N9-dicyclohexylcarbodiimide solution was added to a solution containing MFA(0.49 mmol), and either AMP, Gly, Tau, or NAC (0.49 mmol) separately in 75%pyridine/25% water. The reaction mixture was stirred at 4C for 7 hours and thencentrifuged at 3000g for 5 minutes to remove any N-acylurea derivatives. Thesupernatant was transferred to another culture tube for precipitation by theaddition of acetone (10 ml). The resulting precipitate was isolated by centrifugationat 3000g for 5 minutes followed by further washes with acetone (10 10 ml) and acidified water (pH 4-5) (10 10 ml). For MFA-AMP, theprecipitate was dissolved in 0.1 M potassium phosphate buffer (pH 6) andunderwent continued liquid-liquid washes with ethyl acetate (10 10 ml).Following precipitation via 1 M HCl, the MFA-AMP was further washed withacetone (10 10 ml). The MFA-AMP precipitate was -down to dryness usingN2 gas and weighed out for preparation of a 1 mM MFA-AMP solution inDMSO. For MFA-Gly, MFA-NAC, and MFA-Tau, the initial acetone-derivedprecipitate was dissolved in DMSO and subjected to purification via HPLC/UVmassspectrometry. The correct HPLC eluent fractions, as determined byUV-MS, of each acyl-linked metabolite were collected, blown down to dryness,weighed, and then prepared as 1-mM solutions in DMSO. MFA-AMP eluted ata retention time of 7.6 minutes and showed no impurities when analyzed byHPLC/UV (wavelengths: 220, 254, 262, and 280 nm) and LC-MS via reversephasegradient elution (as described above), and 1H-NMR (Horng and Benet,2013). LC-MS/MS analysis of MFA-AMP revealed collision-induced dissociation(CID) of MH+ ion at m/z 571, m/z (%) yielded: m/z 224 ([M + H - AMP]+,100%), m/z 207 ([M + H - 364]+, 25%), and m/z 136 ([M + H - adenine]+, 28%).MFA-Gly eluted at a retention time of 8.7 minutes (Fig. 2C) and showed noimpurities when analyzed by HPLC/UV (wavelengths: 220, 254, 262, and 280nm) and LC-MS via reverse-phase gradient elution (as described above). LC-MS/MS analysis of MFA-Gly (CID of MH+ ion at m/z 299), m/z (%): m/z 224 ([M +H - Gly]+, 99%), m/z 209 ([M + H - 90]+, 20%), m/z 180 ([M + H - 119]+,18%), m/z 152 ([M + H - 147]+, 4%), m/z 127 ([M + H - 172]+, 2%), m/z 77([Gly + H]+, 1%) (Fig. 2, A and B). MFA-Tau eluted at a retention time of 9.1minutes (Fig. 3C) and showed no impurities when analyzed by HPLC/UV(wavelengths: 220, 254, 262, and 280 nm) and LC-MS via reverse-phasegradient elution (as described above). LC-MS/MS analysis of MFA-Tau (CID ofMH+ ion at m/z 349), m/z (%): m/z 332 ([M + H - H2O]+, 10%), m/z 224 ([M +H - Tau]+, 99%), m/z 209 ([M + H - 140]+, 25%), m/z 180 ([M + H - 169]+,16%), m/z 152 ([M + H - 197]+, 4%), and m/z 126 ([Tau + H+]+, 2%) (Fig. 3, Aand B). MFA-NAC eluted at a retention time of 9.3 minutes (Fig. 4C) andshowed no impurities when analyzed by HPLC/UV (wavelengths: 220, 254, 262,and 280 nm) and LC-MS via reverse-phase gradient elution (as described above).LC-MS/MS analysis of MFA-NAC (CID of MH+ ion at m/z 387), m/z (%): m/z309 ([M + H - 78]+, 30%), m/z 224 ([M + H - NAC]+, 99%), m/z 209 ([M + H -178]+, 18%), m/z 180 ([M + H - 207]+, 13%), and m/z 165 ([NAC + H]+, 3%)(Fig. 4, A and B).

Reference： [1]Drug Metabolism and Disposition,2013,vol. 41,p. 1923 - 1933

67
C₁₄H₂₃N₄O₇P [ No CAS ]
[ 61-19-8 ]
P1-adenosine-5'-P2-cytidine-5'-diphosphate diammonium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₁₄H₂₃N₄O₇P; 5'-adenosine monophosphate With 4,5-dicyano-1H-imidazole In N,N-dimethyl-formamide at 40℃; for 5h; Inert atmosphere; Stage #2: With ammonium bicarbonate In water Inert atmosphere;	6 General procedure for the synthesis of Np₂N′s General procedure: To a solution of nucleoside 5′-phosphoropiperidates (1-4, 0.1mmol) in DMF (2mL) were added NMPs (0.12-0.16mmol) and DCI (0.3-0.35mmol). The reaction was stirred at 40°C for 5h and concentrated in vacuo. The residue was dissolved in NaOAc aqueous solution (3.0M, 1mL). Then, EtOH (25mL) was added. The resulting white precipitate was collected by centrifuge. The crude product was dissolved in deionized H2O (1mL) and loaded onto an ion exchange gel column. Elution with NH4HCO3 buffer (linear gradient 0.2-0.5M), combination of appropriate fractions, and lyophilization gave Np2N′s as the ammonium salts. Passage of the solution of the ammonium salts in deionized H2O through a bed of Dowex 50W-X8 ion exchange resin (Na+ form) and lyophilization afforded dinucleoside diphosphate disodium salts (6-15) as white solids.

Reference： [1]Sun, Qi; Gong, Shan-Shan; Liu, Si; Sun, Jian; Liu, Guo-Dong; Ma, Cha [Tetrahedron, 2014, vol. 70, # 30, p. 4500 - 4506]

68
[ 61-19-8 ]
[ 7659-75-8 ]
P1,P2-diadenosine-5',5'-diphosphate diammonium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 5'-adenosine monophosphate; adenosine (5'-phosphoro-1-piperidinide) With 4,5-dicyano-1H-imidazole In N,N-dimethyl-formamide at 40℃; for 5h; Inert atmosphere; Stage #2: With ammonium bicarbonate In water Inert atmosphere;	3 General procedure for the synthesis of Np₂N′s General procedure: To a solution of nucleoside 5′-phosphoropiperidates (1-4, 0.1mmol) in DMF (2mL) were added NMPs (0.12-0.16mmol) and DCI (0.3-0.35mmol). The reaction was stirred at 40°C for 5h and concentrated in vacuo. The residue was dissolved in NaOAc aqueous solution (3.0M, 1mL). Then, EtOH (25mL) was added. The resulting white precipitate was collected by centrifuge. The crude product was dissolved in deionized H2O (1mL) and loaded onto an ion exchange gel column. Elution with NH4HCO3 buffer (linear gradient 0.2-0.5M), combination of appropriate fractions, and lyophilization gave Np2N′s as the ammonium salts. Passage of the solution of the ammonium salts in deionized H2O through a bed of Dowex 50W-X8 ion exchange resin (Na+ form) and lyophilization afforded dinucleoside diphosphate disodium salts (6-15) as white solids.

Reference： [1]Sun, Qi; Gong, Shan-Shan; Liu, Si; Sun, Jian; Liu, Guo-Dong; Ma, Cha [Tetrahedron, 2014, vol. 70, # 30, p. 4500 - 4506]

69
[ 61-19-8 ]
[ 110326-59-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium periodate; sodium hydroxide In water at 45℃; for 3h;	Compound of Formula (I) The following synthesis protocol is followed: dissolve 1 equivalent of AMP in water (to a concentration of about 0.3M), adjust the solution pH to 8.4 with NaOH (2M). Add 1 equivalent of NaIO4 to the mixture. Maintain the reaction at room temperature for 5 minutes and then at 45° C. for three hours. Then carry out silica chromatography, after removing the water from the initial solution by lyophilization. Dissolve the crude lyophilized product in chloroform and methanol, mix with silica, and dry the mixture and load it in the top of the silica column. Elute the column with 95/5 chloroform/methanol solution, recovering the desired product at high purity.

Reference： [1]Current Patent Assignee: MEDESTEA RESEARCH & PRODUCTION S.P.A. - US2014/243359, 2014, A1 Location in patent: Paragraph 0025

70
[ 58-97-9 ]
[ 61-19-8 ]
double stranded RNA (polyadenylic acid-polyuridylic acid) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With lithium chloride In water at 85℃; for 8h; Inert atmosphere;	7 EXAMPLE 7: Increasing polymer yield synthesis- based on manuscript As previously, two monomers were chosen adenosine 5’-monophosphate (AMP) and uridine 5’-monophosphate (UMP) in their acid forms rather than as sodium salts (Sigma-Aldrich). When dissolved in water at 10 mM concentration the pH of the solution is 2.5. Commercial polyadenylic acid (polyA) and polyuridylic acid (polyU) were used as polynucleotide control standards (Sigma-Aldrich). These were mixed in 1:1 mole ratios with respect to the bases to produce double stranded RNA (polyA-polyU). The effects on oligomerization of a variety of monovalent salts, including LiC1, NaC1, KC1, and NH4C1 weretested. During evaporation, the salts formed crystalline films when their solubility was exceeded. The growing crystals excluded other solutes such as the mononucleotides, producing highly concentrated eutectic phases within the salt matrix. A laboratory simulation of HD cyclesSimulations were carried out using glass slides with two wells on each slide that hold0.1 mL of the reaction mixture. Four slides were arranged on a laboratory hot plate set at thedesired temperature range, and a plastic flow box with 8 small holes (1 mm diameter) was set on the slides. Each hole was placed directly over a well so that carbon dioxide gas flowed onto the mixture at approximately 1 cc/sec into each well. The gas was used to exclude oxygen, but also to carry away water vapor from condensation reaction as ester bondsformed, thereby preventing hydrolytic back reactions. Reaction mixturesMononucleotides, AMP (10 mM) and UMP (10 mM), were initially mixed in a 1:1 volume ratio. The mononucleotides solution and 0.1 M monovalent salts were mixed in a 2:1 volume ratio so that the initial concentrations were 3.3 mM AMP and UMP, together with0.033 M salt. Because water evaporated during dehydration, these dilute solutions become highly concentrated and finally dry, so it is the ratios that are significant rather than the initial concentrations. In a typical experiment, the reactants were exposed to 1-16 cycles of wetting and drying. The temperature (85° C) and flow of carbon dioxide caused drying within 1 - 2 minutes. After each dehydration phase of 30 minutes, the samples were dispersed in 0.1 mLof 1.0 mM HC1 to maintain acidity, followed by the next dehydration cycle. Variable experimental parameters included initial pH, temperature, the time given to each cycle and the numbers of cycles. At the end of the cycle series, the samples were dissolved in 0.1 mL of water. Isolation of productsThe polymer products were isolated by standard precipitation in ethanol (2.5 X volume ethanol 100%, 1/10 volume sodium acetate 3 M pH 5.2, 1.6 jiL linear acrylamide 5 mg/mL (Fischer scientific) for 700 jiL of reaction mixtures, followed by incubation at - 20°C overnight). The pellets were consistent with polymers that behaved like RNA. Quantitative analysis was performed by UV absorbance with a NanoVue instrumentcalibrated for RNA to estimate yields of products. Depending on the conditions, typical yields ranged from 1% to 40% expressed as the fraction of the total weight of mononucleotides present, and over 55% if additional monomers were added during cycling.Characterization of productsAs described above, double-stranded polynucleotide structure was shown by ethidiumbromide, alkaline hydrolysis, RNase hydrolysation, hypochromicity, nanopore analysis andmicroscopy. Effect of monovalent cations on polymerizationWhen the HD cycles were run with monovalent salts in the reaction mixture, yields ofpolymer were dramatically increased compared to absence of salts. Furthermore, the productswere stained by ethidium bromide, an intercalating dye, suggesting that base stacking was present. Sodium, potassium and ammonium chloride all promoted synthesis of polymers containing AMP and UMP as monomers. Products ranging from 10 to 300 nucleotides with a peak around 100 mers were detected. NH4C1 had the greatest effect, but products from LiC1produced only a weak band in the gel even though the yield measured by ethanol precipitation was in the same range as NH4C1 (Table 2). The A260/A280 ratio provides an estimate of how much of the absorbance is due to polymers and how much to monomers. A ratio of 2 corresponds to RNA while a ratio of 3.4 is observed for monomers. The high ratio with LiC1 indicates that the product has relatively short strands of oligomer lacking base stacking compared with the other salts.Mixtures of AMP 10 mM + UMP 10 mM + monovalent salt 0.1 M (LiC1, KC1, NaC1 and NH4C1) in 1:1:1 volume ratio were submitted to 16 HD cycles of 30 minutes. Table 2 below shows yields of polymers synthesized and ratio A260/A280 measured by UV absorbance with a NanoVue instrument. Yields are values from duplicate samples, and were calculated as the percent by weight of the original AMP and UMP present in the mixtureTable 2. Effect of monovalent salts on polymerization.SaltYield (%)A260/A280LiC138; 423.4NaC116; 182.1KC125; 292.0NH4C134; 372.0Yields were highest with LiC1, NH4C1, KC1 and NaC1, in that order, but the LiC1product was less stained by ethidium, probably because the oligomers were shorter withdecreased base stacking.Cycling increases yield of polymersThe optimum conditions for the polymerization process were determined by performing a set of experiments using a variety of controls and conditions including thenumber of cycles, duration of the cycles, pH and temperature. The synthesis of polymers is the most efficient at high temperature (around 85 °C), at acidic pH (3) and in the presence of CO2 stream. Without wishing to be bound by any theory, the above suggests that synthesis of the ester bond is an acid catalyzed mechanism and that CO2 plays an essential role in the polymerization process. Most of the product appeared to be polymers from 10 to 300nucleotides long. Finally, the dehydration phase appeared to be essential for the polymerization process since a minimum of 30 minutes of drying at each cycle is necessary to synthesize the 300 nt species (data not shown). Role of NH4 cations in promoting polymerizationBecause NH4C1 seemed to have the greatest effect on yields of polymers, a series of further experiments were conducted. Figure 3 shows results with different ammonium salts, including ammonium phosphate, ammonium molybdate, and ammonium formate. Only the ammonium formate yielded polymers ranging from 10 to 300 nucleotides in length but inlesser amounts compared to ammonium chloride. The importance of the chemical effect of the ammonium cation in this polymerization process was also tested by substituting tetramethylammonium chloride for ammonium chloride. Fig. 14 shows polymer synthesis after 8 hours of 30 minutes HD cycles. Yields are normalized for comparison, taking the products in the presence of NH4C1 as 1.0. Salts, lane A: NH4C1; lane B: C19H42BrN; lane C:HCO2NH4 lane D: (NH4)6Mo7O244H2O; lane E: NH4H2PO4. Fig.14 shows that tetramethylammonium chloride also produced polymers ranging from 10 to 300 nucleotides in length but with lower efficiency than ammonium chloride. This suggests that NH4 might have chemical effects induced by its protons coupled to the ordering effects on the mononucleotides.Kinetics of oligomerizationThe oligomerization process in the presence of ammonium chloride follows anexponential curve, and reaches a plateau after 30 hours of wet-dry cycles with a yield of 40%(Fig. 15). Fig. 15 shows results from Mixture of AMP 10 mM + UMP 10 mM + NH4C1 0.1M (1:1:1 volume ratio) showing the total amount and yield of products over multiple cycles.Each hour has two 30 minutes cycles, so 40 hours represents 80 cycles.Control of nucleotide concentration: nucleotide feedingTo determine whether the plateau was due to exhaustion of monomers, a feeding experiment was performed in which fresh monomers were added every 2 hours (4 cycles).An enhancement of oligomerization occurred when cycling is accompanied by regular additions of monomers. A yield of 58% is obtained after 5 feeding steps (final concentration of nucleotides equal to 60 mM) whereas for the same concentration (60 mM) present at the beginning of the experiment, the yield is 37%. This means that controlling nucleotides concentration by stepwise additions enhances the polymerization process in comparison to nucleotide pooi at an equivalent concentration.The plateau can be due to an equilibrium between synthesis and hydrolysis, although degradation of nucleotides over time may also contribute. Figure 6 shows that longerproducts accumulate in later cycles. Indeed, there is an enhancement of the production of short fragments (10 and 150 nts) after few cycles, and then their presence decreases as a function of time whereas the long polymers (700 and 1000 nts) accumulate in the later cycles. Lengthening may occur either by elongation and/or by ligation of short fragments.

Reference： [1]Current Patent Assignee: UNIVERSITY OF CALIFORNIA; SORBONNE UNIVERSITY - WO2015/42073, 2015, A1 Location in patent: Page/Page column 24; 25; 26

71
[ 1172-42-5 ]
[ 61-19-8 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 3982 - 3997

72
[ 2591-17-5 ]
[ 61-19-8 ]
D-luciferyl adenylate [ No CAS ]
[ 17002-50-5 ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 7592 - 7595

73
[ 61-19-8 ]
[ 10387-40-3 ]
[ 55062-28-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With hexacyanoferrate(III); sodium hydroxide In water; water-d2 Inert atmosphere;	Protocol C: Nucleoside/nucleotide (2; 100mM) and N-acetyl imidazole (1a; 1-10 eq.) weredissolved in D2O/H2O (1:1). The solution pH was stabilised at the desired value throughaddition of 4M HCl/NaOH and the reaction monitored by NMR spectroscopy. The productwas purified by reverse-phase (C18) flash column chromatography (eluted at pH 4 with100mM NH4HCO2/MeCN 98:2 to 80:20). The fractions containing 5 were lyophilised toyield a white powder.

Reference： [1]Fernández-García, Christian; Powner, Matthew W. [Synlett, 2017, vol. 28, # 1, p. 78 - 83]

74
[ 61-19-8 ]
[ 98-59-9 ]
[ 28220-12-4 ]

Yield	Reaction Conditions	Operation in experiment
97.6%	Stage #1: 5'-adenosine monophosphate With sodium hydroxide In 1,4-dioxane at 5 - 15℃; for 0.5h; Stage #2: p-toluenesulfonyl chloride In 1,4-dioxane at -15 - 5℃; for 18h;	1 Synthesis of Intermediate 1 Adenosine monophosphate (348g, 1.0mol) was added to 1.5 L of 1,4-dioxane, stirred for 10 minutes, the resulting solution was cooled to below 0 ~ 10 , 3.5L was slowly added aqueous sodium hydroxide (1.0mol / L), the temperature control system 5 ~ 15 .The resulting mixed solution was continued for 30 minutes, cooled to -15 ~ 0 , 1,4-dioxane was slowly added dropwise a solution of p-toluenesulfonyl chloride (tosyl chloride dissolved in 229g 1.0L dioxane), process control temperature of the reaction system at 0 ~ 5 , further stirred for 18 hours after addition was complete.In general not more than 30 degrees Celsius above the concentrator resulting solution was concentrated to 4L, dilute hydrochloric acid was added to adjust the pH to 4.0, after mixing, left at room temperature overnight, the solid was collected by filtration to give 489g of Intermediate 1, 97.6% yield.
46.4 g	With sodium hydroxide In 1,4-dioxane at 0℃; for 15h;	9.1 (1) Preparation of 2-oxo-p-toluenesulfonyl ester-5-adenosine (II) Add 34.7 grams of 5-AMP to a mixed solution of 150 milliliters of dioxane and 350 milliliters of 1 equivalent sodium hydroxide;After dissolving, add 22.8 grams of finely ground p-toluenesulfonyl chloride to this solution,After stirring the reaction at 0°C for 15 hours,Add 35 ml of 6 equivalents of hydrochloric acid to adjust the pH to 4.0.The precipitated crystals were filtered to obtain 46.4 g of crystalline powder II.

Reference： [1]Current Patent Assignee: GANSU CHENGJI BIOPHARMACEUTICAL CO., LTD. - CN107056862, 2017, A Location in patent: Paragraph 0058-0061
[2]Current Patent Assignee: HAINAN JINRUI PHARMACEUTICAL - CN113173957, 2021, A Location in patent: Paragraph 0074; 0076-0077; 0086

75
[ 61-19-8 ]
[ 104619-51-4 ]
[ 20816-58-4 ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 511 - 514

76
((2R,3R,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3-hydroxy-4-(prop-2-yn-1-yloxy)tetrahydrofuran-2-yl)methyl hydrogen phosphate [ No CAS ]
[ 61-19-8 ]
1-((2R,3R,4R,5R)-5-((((((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)oxidophosphoryl)oxy)methyl)-4-hydroxy-3-(prop-2-yn-1-yloxy)tetrahydrofuran-2-yl)-3-carbamoylpyridin-1-ium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: 5'-adenosine monophosphate With triethylamine; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 14h; Stage #2: ((2R,3R,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3-hydroxy-4-(prop-2-yn-1-yloxy)tetrahydrofuran-2-yl)methyl hydrogen phosphate In N,N-dimethyl-formamide at 20℃; for 96h;	1 [0319] General procedure for the synthesis of l-((2R,3R,4R,5R)-5-((((((((2R,3S,4R,5R)-5-(6- amino-9H-purin-9-yl)-3,4-dihydr-oxytetrahydrofuran-2-yl)methoxy)(hydroxy)p- hosphoryl)oxy)oxidophosphoryl)o-xy)methyl)-4-hydroxy-3-(prop-2-yn-l-yloxy)tet- rahydrofuran-2-yl)-3-carbamoy-lpyridin-l-ium (10, NAD+ 1): To a stirred solution of Adenosine 5 '-monophosphate (5'-AMP) (52 mg, 0.15 mmol, 1.5 eq) in dried DMF (2 mL) were added 1, 1-carbonyldiimidazole (CDI) (63 mg, 0.50 mmol, 5 eq) and triethylamine (23 μ., 0.16 mmol. 1.6 eq). The reaction mixture was stirred at room temperature for 14 hours, and then quenched with 0.100 ml dried methanol. The solvent was removed under vacuum and the residue was coevaporated 3 times each with 1.00 ml of dried DMF. The activated 5'- AMP was dissolved in dried DMF (1 mL) and compound (9, NM1) (37 mg, 0.10 mmol, 1.0 eq) was added. After stirring at room temperature for 4 days, H20 was added to quench the reaction at 0 °C. The resulting mixture was continued stirring at room temperature for 24 hours. The reaction was then concentrated in vacuo and the crude product was purified via preparative HPLC (C18-A column, 150X4.6 mm, 5 μπι) (mobile phase A: 0.1% formic acid (aq), mobile B: 0.1% formic acid in acetonitrile; flow rate = 1.0 ml/min; 0-16 min: 0-6.7% B, 16-18 min: 6.7-0%) B). Fractions containing the desired product were concentrated and lyophilized to yield NAD+ 1 (32 mg, 45%> yield) as a colorless solid. (0549) [0320] l-((2R,3R,4R,5R)-5-((((((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydr- oxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)oxidophosphoryl)o-xy)methyl)- 4-hydroxy-3-(prop-2-yn-l-yloxy)tetrahydrofuran-2-yl)-3-carbamoy-lpyridin-l-ium (10, NAD+ 1). 1H NMR (400 MHz, D20): δ 2.87 (br, 1H, CH), 4.12-4.14 (m, 1H, CH), 4.24-4.33 (m, 5H, 2CH2+CH), 4.40 (br, 1H, CH), 4.51 (t, 1H, J= 4.0 Hz, CH2), 4.63 (d, 1H, J= 2.8 Hz, CH), 4.71 (t, 1H, J= 5.2 Hz, CH), 4.87-4.89 (m, 2H, 2CH), 6.06 (d, 1H, J= 5.2 Hz, CH), 6.59 (d, 1H, J= 5.6 Hz, CH), 8.09-8.13 (m, 1H, ArH), 8.31 (br, 1H, ArH), 8.61 (br, 1H, ArH), 8.86 (d, 1H, J= 8.0 Hz, ArH), 8.01 (d, 1H, J= 6.0 Hz, ArH), 9.19 (s, 1H, ArH); 13C NMR (100 MHz, D20): δ 59.0, 65.2, 69.3, 70.2, 74.6, 76.7, 78.5, 78.7, 84.1, 87.3, 87.9, 95.6, 126.8, 132.1, 140.9, 143.7, 145.0, 147.6, 148.5, 151.8, 165.2.; HRMS (ESI) Calcd. For C24H28N7Na2Oi4P2+ (M+H)+ requires 746.0965, Found: 746.0955.

Reference： [1]Current Patent Assignee: UNIVERSITY OF SOUTHERN CALIFORNIA - WO2018/227168, 2018, A1 Location in patent: Paragraph 0319-0320

77
((2R, 3R,4R, 5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3-hydroxy-4-(pent-4-yn-1-yloxy)tetrahydrofuran-2-yl)methyl hydrogen phosphate [ No CAS ]
[ 61-19-8 ]
C₂₆H₃₃N₇O₁₄P₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: 5'-adenosine monophosphate With triethylamine; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 14h; Stage #2: ((2R, 3R,4R, 5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3-hydroxy-4-(pent-4-yn-1-yloxy)tetrahydrofuran-2-yl)methyl hydrogen phosphate In N,N-dimethyl-formamide at 20℃; for 96h;	2 [0346] General procedure for the synthesis of (NAD+ 3): To a stirred solution of Adenosine 5 '-monophosphate (5' -AMP) (52 mg, 0.15 mmol, 1.5 eq) in dried DMF (2 mL) were added 1, 1-carbonyldiimidazole (CDI) (63 mg, 0.50 mmol, 5 eq) and triethylamine (23 μ FontWeight="Bold" FontSize="10" , 0.16 mmol. 1.6 eq). The reaction mixture was stirred at room temperature for 14 h, and then quenched with 0.100 ml dried methanol. The solvent was removed under vacuum and the residue was coevaporated 3 times each with 1.00 ml of dried DMF. The activated 5'-AMP was dissolved in dried DMF (1 mL) and compound (3-9) (0.10 mmol, 1.0 eq) was added. After stirring at room temperature for 4 days, H20 was added to quench the reaction at 0 °C. The resulting mixture was continued stirring at room temperature for 24 hours. The reaction was then concentrated in vacuo and the crude product was purified via preparative HPLC. Fractions containing the desired product were concentrated and lyophilized to yield corresponding NAD+ 3. [0347] NAD+ 3. A colorless solid, 45% yield; 1H NMR (400 MHz, D20): δ 1.57-1.66 (m, 2H, CH2), 1.95-2.12 (m, 2H, CH2), 2.29 (t, 1H, J= 2.4 Hz, CH), 3.63-3.76 (m, 2H, CH2), 4.13-4.16 (m, 1H, CH2), 4.24-4.39 (m, 3H, CH2+CH2), 4.40 (d, 1H, J= 2.0 Hz, CH), 4.52 (t, 1H, J= 4.4, CH), 4.60 (dd, 1H, J= 4.4, 1.6 Hz, CH), 4.71 (t, 1H, J= 5.6 Hz, CH), 4.76 (dd, 1H, J= 5.6 Hz, CH), 4.92 (br, 1H, CH), 6.10 (d, 1H, J= 6.6 Hz, CH), 6.63 (d, 1H, J= 6.0 Hz, CH), 8.17 (dd, 1H, J= 8.0, 6.0 Hz, ArH), 8.40 (s, 1H, ArH), 8.61 (s, 1H, ArH), 8.92 (d, 1H, J= 8.0 Hz, ArH), 9.08 (d, 1H, J= 6.0 Hz, ArH), 9.25 (s, 1H, ArH); HRMS (ESI) Calcd. For C26H34N2Oi4P2+ (M+H)+ requires 730.1633, Found: 730.1639.

Reference： [1]Current Patent Assignee: UNIVERSITY OF SOUTHERN CALIFORNIA - WO2018/227168, 2018, A1 Location in patent: Paragraph 0346-0347

78
((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-4-hydroxy-3-(prop-2-yn-1-yloxy)tetrahydrofuran-2-yl)methyl hydrogen phosphate [ No CAS ]
[ 61-19-8 ]
C₂₄H₂₉N₇O₁₄P₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	Stage #1: 5'-adenosine monophosphate With triethylamine; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 14h; Stage #2: ((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-4-hydroxy-3-(prop-2-yn-1-yloxy)tetrahydrofuran-2-yl)methyl hydrogen phosphate In N,N-dimethyl-formamide at 20℃; for 96h;	3 [0379] General procedure for the synthesis of NAD+ analogue 7 and 9: To a stirred solution of Adenosine 5 '-monophosphate (5'-AMP) (52 mg, 0.15 mmol, 1.5 eq) in dried DMF (2 mL) were added 1, 1-carbonyldiimidazole (CDI) (63 mg, 0.50 mmol, 5 eq) and triethylamine (23 μ., 0.16 mmol. 1.6 eq). The reaction mixture was stirred at room temperature for 14 hours, and then quenched with 0.100 ml dried methanol. The solvent was removed under vacuum and the residue was coevaporated 3 times each with 1.00 ml of dried DMF. The activated 5'- AMP was dissolved in dried DMF (1 mL) and compound (7-8) or 9-8 (0.10 mmol, 1.0 eq) was added. After stirring at room temperature for 4 days, H20 was added to quench the reaction at 0 °C. The resulting mixture was continued stirring at room temperature for 24 hours. The reaction was then concentrated in vacuo and the crude product was purified via preparative HPLC. Fractions containing the desired product were concentrated and lyophilized to yield the corresponding NAD+ 7 and NAD+ 9 . [0380] NAD+ analogue 7. A colorless solid, 40% yield; 1H NMR (400 MHz, D20): δ 2.91 (t, 1H, J= 2.0 Hz, CH), 4.25 (br, 3H, CH2+CH2), 4.35-4.44 (m, 5H, 2CH2+CH), 4.51 (br, 1H, CH), 4.64 (t, 1H, J= 5.2, CH), 4.73-4.77 (m, 2H, 2CH),,6.11-6.13 (m, 2H, 2CH), 8.24-8.28 (m, 1H, ArH), 8.32 (br, 1H, ArH), 8.65 (br, 1H, ArH), 8.90 (d, 1H, J= 7.6 Hz, ArH), 9.22 (d, 1H, J= 5.6 Hz, ArH), 9.39 (s, 1H, ArH); HRMS (ESI) Calcd. For C24H28N7Na2Oi4P2+ (M+2Na-2H)+ requires 746.0965, Found: 746.0958.

Reference： [1]Current Patent Assignee: UNIVERSITY OF SOUTHERN CALIFORNIA - WO2018/227168, 2018, A1 Location in patent: Paragraph 0379-0380

79
[ 1355216-06-6 ]
[ 61-19-8 ]
C₂₁H₂₆N₁₀O₁₃P₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: 5'-adenosine monophosphate With triethylamine; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 14h; Stage #2: ((2S,3S,4R,5R)-3-azido-5-(3-carbamoylpyridin-1-ium-1-yl)-4-hydroxytetrahydrofuran-2-yl)methyl hydrogen phosphate In N,N-dimethyl-formamide at 20℃; for 96h;	4 [0408] General procedure for the synthesis of NAD+ 19: To a stirred solution of Adenosine 5 '-monophosphate (5'-AMP) (52 mg, 0.15 mmol, 1.5 eq) in dried DMF (2 mL) were added 1, 1-carbonyldiimidazole (CDI) (63 mg, 0.50 mmol, 5 eq) and triethylamine (23 μ FontWeight="Bold" FontSize="10" , 0.16 mmol. 1.6 eq). The reaction mixture was stirred at room temperature for 14 hours, and then quenched with 0.100 ml dried methanol. The solvent was removed under vacuum and the residue was coevaporated 3 times each with 1.00 ml of dried DMF. The activated 5'-AMP was dissolved in dried DMF (1 mL) and compound 6dd (0.10 mmol, 1.0 eq) was added. After stirring at room temperature for 4 days, H20 was added to quench the reaction at 0 °C. The resulting mixture was continued stirring at room temperature for 24 hours. The reaction was then concentrated in vacuo and the crude product was purified via preparative HPLC. Fractions containing the desired product were concentrated and lyophilized to yield NAD+ 19 . [0409] NAD+ 19. A colorless solid, 45% yield; 1H NMR (400 MHz, D20): δ 4.18-4.25 (m, 2H, CH2), 4.38-4.41 (m, 2H, CH2), 4.49-4.53 (m, 2H, 2CH), 4.59 (br, 1H, CH), 4.71 (t, 1H, J = 5.6 Hz, CH), 4.68-4.80 (1H, CH, overlapped with solvent residue peak), 4.83 (t, 1H, J= 5.6 Hz, CH), 6.12 (d, 1H, J= 5.2 Hz, CH), 6.16 (d, 1H, J= 5.2 Hz, CH), 8.27-8.30 (m, 1H, ArH), 8.39 (s, 1H, ArH), 8.58 (s, 1H, ArH), 8.94 (d, 1H, J= 8.0 Hz, ArH), 9.25 (d, 1H, J = 6.4 Hz, ArH), 9.40 (s, 1H, ArH); 13C NMR (100 MHz, D20): δ 62.3, 65.02 (d, J= 5.3 Hz), 65.06 (d, J= 3.6 Hz), 70.1, 74.5, 77.7, 84.0 (d, J= 8.3 Hz), 84.9 (d, J= 8.9 Hz), 87.7, 99.3, 118.3, 128.6, 133.8, 139.8, 142.2, 142.5, 145.0, 146.1, 148.2, 149.9, 165.4, 165.8; HRMS (ESI) Calcd. For C2iH27Ni0Oi3P2+ (M+H)+ requires 689.1234, Found: 689.1226. Exam le 5. Synthesis of NAD+ 20 and NAD+ 26

Reference： [1]Current Patent Assignee: UNIVERSITY OF SOUTHERN CALIFORNIA - WO2018/227168, 2018, A1 Location in patent: Paragraph 0408-0409

80
1-((2R,3R,4S,5R)-3-azido-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3-carbamoylpyridin-1-ium bromide [ No CAS ]
[ 61-19-8 ]
C₂₁H₂₆N₁₀O₁₃P₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: 5'-adenosine monophosphate With triethylamine; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 14h; Stage #2: 1-((2R,3R,4S,5R)-3-azido-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3-carbamoylpyridin-1-ium bromide In N,N-dimethyl-formamide at 20℃; for 96h;	5 [0427] General procedure for the synthesis of (NAD+ analogue 20 and 26): To a stirred solution of Adenosine 5 '-monophosphate (5'-AMP) (52 mg, 0.15 mmol, 1.5 eq) in dried DMF (2 mL) were added 1,1-carbonyldiimidazole (CDI) (63 mg, 0.50 mmol, 5 eq) and triethylamine (23 μ., 0.16 mmol. 1.6 eq). The reaction mixture was stirred at room temperature for 14 hours, and then quenched with 0.100 ml dried methanol. The solvent was removed under vacuum and the residue was coevaporated 3 times each with 1.00 ml of dried DMF. The activated 5'-AMP was dissolved in dried DMF (1 mL) and compound 8ee (0.10 mmol, 1.0 eq) was added. After stirring at room temperature for 4 days, H20 was added to quench the reaction at 0 °C. The resulting mixture was continued stirring at room temperature for 24 hours. The reaction was then concentrated in vacuo and the crude product was purified via preparative HPLC. Fractions containing the desired product were concentrated and lyophilized to yield the NAD+ 20 and 26. [0428] NAD+ 20. A colorless oil, 69% yield; 1H NMR (400 MHz, D20): δ 4.15-4.19 (m, 1H, CH), 4.24-4.30 (m, 3H, CH2+CH2), 4.40-4.41 (m, 1H, CH), 4.53 (dd, 1H, J= 5.2, 4.0 Hz, CH), 4.73-4.77 (m, 2H, 2CH), 4.92 (br, 1H, CH), 5.14 (dd, 1H, J= 6.4, 5.2 Hz, CH), 6.11 (d, 1H, J= 5.6 Hz, CH), 6.68 (d, 1H, J= 6.0 Hz, CH), 8.18 (dd, 1H, J= 8.0, 6.4 Hz, ArH), 8.40 (s, 1H, ArH), 8.62 (s, 1H, ArH), 8.92-8.94 (m, 1H, ArH), 9.08 (d, 1H, J= 6.4 Hz, ArH), 9.27 (s, 1H, ArH); HRMS (ESI) Calcd. For C2iH27NioOi3P2+ (M+H)+ requires 689.1234, Found: 689.1250.

Reference： [1]Current Patent Assignee: UNIVERSITY OF SOUTHERN CALIFORNIA - WO2018/227168, 2018, A1 Location in patent: Paragraph 0427-0428

81
[ 10065-72-2 ]
[ 61-19-8 ]
C₁₄H₂₀N₆O₈P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In aq. buffer at 25℃; for 24h;

Reference： [1]Egli, Martin; Jovanovic, Dejana; Pallan, Pradeep S.; Richert, Clemens; Tremmel, Peter [Angewandte Chemie - International Edition, 2020, vol. 59, # 45, p. 20154 - 20160][Angew. Chem., 2020, vol. 132, # 45, p. 20329 - 20335,7]

82
[ 61-19-8 ]
[ 616-34-2 ]
adenosine 5'-monophosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In aq. buffer at 25℃; for 48h;

Reference： [1]Egli, Martin; Jovanovic, Dejana; Pallan, Pradeep S.; Richert, Clemens; Tremmel, Peter [Angewandte Chemie - International Edition, 2020, vol. 59, # 45, p. 20154 - 20160][Angew. Chem., 2020, vol. 132, # 45, p. 20329 - 20335,7]

83
[ 6384-18-5 ]
[ 61-19-8 ]
C₁₆H₂₂N₆O₁₀P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In aq. buffer at 25℃; for 48h;

Reference： [1]Egli, Martin; Jovanovic, Dejana; Pallan, Pradeep S.; Richert, Clemens; Tremmel, Peter [Angewandte Chemie - International Edition, 2020, vol. 59, # 45, p. 20154 - 20160][Angew. Chem., 2020, vol. 132, # 45, p. 20329 - 20335,7]

84
[ 2577-48-2 ]
[ 61-19-8 ]
prolinyladenosine-5'-monophosphate methylester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In aq. buffer at 25℃; for 8h;

Reference： [1]Egli, Martin; Jovanovic, Dejana; Pallan, Pradeep S.; Richert, Clemens; Tremmel, Peter [Angewandte Chemie - International Edition, 2020, vol. 59, # 45, p. 20154 - 20160][Angew. Chem., 2020, vol. 132, # 45, p. 20329 - 20335,7]

85
[ 693-98-1 ]
[ 61-19-8 ]
C₁₄H₁₇N₇O₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 25℃; for 4h; Inert atmosphere;
	Stage #1: 2-methylimidazole; 5'-adenosine monophosphate With hydrogenchloride; sodium hydroxide In water Stage #2: With 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine In dimethyl sulfoxide at 20℃; for 0.5h; Inert atmosphere;

Reference： [1]Egli, Martin; Jovanovic, Dejana; Pallan, Pradeep S.; Richert, Clemens; Tremmel, Peter [Angewandte Chemie - International Edition, 2020, vol. 59, # 45, p. 20154 - 20160][Angew. Chem., 2020, vol. 132, # 45, p. 20329 - 20335,7]
[2]Zhang, Stephanie J.; Duzdevich, Daniel; Szostak, Jack W. [Journal of the American Chemical Society, 2020, vol. 142, # 35, p. 14810 - 14813]

86
[ 61-19-8 ]
ribose 5-monophosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogenchloride In water at 100℃; for 1h;	The ribose 5′-monophosphate was chemically synthesized by depurination reaction of AMP in acidic conditions. 500.0mg of AMP (1.4 mmol) was stirred in 30 mL of 1 M aqueous HCl at 100 °C for an hour. Then, the reaction mixture was cooled to room temperature and adjusted to pH 8.2 with saturated aqueous KOH solution. The mixture was desalted by isopropanol precipitation three times and crude ribose 5′-monophosphate was obtained as pellets. The crude product was purified with Dowex 1x8 anion exchange column using a step-gradient of monochloroacetic acid solution from 0 to 1.0 M (0, 0.25, 0.5, 0.75, and 1.0 M). The purified ribose 5′- monophosphate was obtained by lyophilization and analyzed by 400 MHz Bruker NMR (D2O as solvent) with water-gate solvent suppression (Supplemental Information Fig. S2). The yield was 300.0 mg (95%).

Reference： [1]Clerc, Elliot P.; Riley, Andrew T.; Sanford, Tristan C.; Sumita, Minako; Woodard, Austin M. [Bioorganic and Medicinal Chemistry Letters, 2021, vol. 44]

87
[ 136-08-3 ]
[ 61-19-8 ]
adenosine thiamine triphosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; dicyclohexyl-carbodiimide In water at 50℃; for 3h;	2.6. Chemical synthesis and purification of AThTP AThTP was synthesized by condensing ThDP and AMP in pyridine in the presence of DCC. The routine procedure for the preparation of AThTP was as follows. Weighed amounts of AMP (0.55 mmol) and ThDP (0.46 mmol) were dissolved each in 0.68 ml of H2O, put in 137 ml of warmed up to 50 C pyridine and thoroughly stirred until being complete dissolved. Then 13.7 g of DCC was added and the final reaction mixture, containing 1.38 mg/ml of ThDP, 1.36 mg/ml of AMP and 96mg/ml of DCC, was let stand for 3 h at 50 C. Afterward, the reaction medium was transferred to 500 ml of absolute ethanol and the mixture was placed in a freezer at 20 C to precipitate the products. The precipitate formed was collected by centrifugation (5000 g, 10 min), dissolved in 8 ml of 5 mM Na-acetate buffer, pH 3.8, and passed through acolumn of SP Sephadex C-25 (2.5 × 20 cm) equilibrated with the same buffer (flow rate 10 cm/h). Fractions of 3 ml were collected and those ones containing AThTP were combined, adjusted to pH 7.0 with 0.5 MTris-HCl, pH 8.9, and applied to a DEAE Sephadex A-25 column (2.5 ×20 cm) equilibrated with 10 mM Tris-HCl buffer, pH 7.2. After washing the column, elution was carried out with a linear gradient of increasingNaCl concentration from 0 to 0.3 M (250 ml both in the mixing chamberand reservoir) at a flow rate of 15 cm/h. The volume of a fraction was 5ml. Then the AThTP fractions were pooled, evaporated to 1 ml and precipitated with 100 ml of absolute ethanol at 20 C. Finally, theprecipitate was collected by centrifugation (5000 g, 10 min), dissolved in 5 ml of 5 mM Na-acetate buffer, pH 3.8, and chromatographed repeatedly on the column of SP-Sephadex C-25. The fractions of AThTP peak were stored frozen at 20 C.

Reference： [1]Kolas, Iryna K.; Kudyrka, Tatsiana G.; Luchko, Tatyana A.; Makar, Alena A.; Makarchikov, Alexander F.; Rusina, Iryna M.; Usanov, Sergey A.; Yantsevich, Aliaksei V. [Biochimica et Biophysica Acta - General Subjects, 2022, vol. 1866, # 4]

88
[ 7647-01-0 ]
potassium aquapentachlororuthenate(III) [ No CAS ]
[ 61-19-8 ]
C₁₀H₁₂Cl₆N₁₀Ru₂⁽²⁺⁾*2Cl^(1-)*2H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	at 90℃; for 72h;	2.2.1 Synthesis of [{Ru(μ-Cl)(μ-Hade)}₂Cl₄]Cl₂·2H₂O (1) A solvothermal reaction of K2[RuCl5(H2O)] (11.2mg, 0.03mmol) and adenosine 5′-monophosphate monohydrate (11.0mg, 0.03mmol) was carried out in HCl (4mL, 3.0M) at 90°C for 3days, followed by a 12h cooling process to room temperature. Dark brown plates of 1 were thus grown and were suitable for X-ray diffraction studies. Yield: ca. 65%. Anal. Calcd. for C10H16Cl8N8O2Ru2: C, 15.1; H, 2.0; N, 17.6. Found: C, 15.2; H, 1.9; N, 17.7. SEM-EDX: a molar ratio of 1:4 for Ru/Cl was found for 1. IR peaks (KBr pellets, ν/cm-1): 3405(m), 3327(m), 3116(m), 3056(m), 2955(m), 2923(m), 2853(m), 1706(vs), 1653(m), 1616(m), 1559(m), 1521(w), 1466(s), 1404(m), 1320(m), 1234(s), 1180(m), 1135(m), 940(w), 800(w), 669(w), 608(m), 562(m), 414(w).
65%	at 90℃; for 72h;	2.2.1 Synthesis of [{Ru(μ-Cl)(μ-Hade)}₂Cl₄]Cl₂·2H₂O (1) A solvothermal reaction of K2[RuCl5(H2O)] (11.2mg, 0.03mmol) and adenosine 5′-monophosphate monohydrate (11.0mg, 0.03mmol) was carried out in HCl (4mL, 3.0M) at 90°C for 3days, followed by a 12h cooling process to room temperature. Dark brown plates of 1 were thus grown and were suitable for X-ray diffraction studies. Yield: ca. 65%. Anal. Calcd. for C10H16Cl8N8O2Ru2: C, 15.1; H, 2.0; N, 17.6. Found: C, 15.2; H, 1.9; N, 17.7. SEM-EDX: a molar ratio of 1:4 for Ru/Cl was found for 1. IR peaks (KBr pellets, ν/cm-1): 3405(m), 3327(m), 3116(m), 3056(m), 2955(m), 2923(m), 2853(m), 1706(vs), 1653(m), 1616(m), 1559(m), 1521(w), 1466(s), 1404(m), 1320(m), 1234(s), 1180(m), 1135(m), 940(w), 800(w), 669(w), 608(m), 562(m), 414(w).

Reference： [1]Castro, Isabel; Gil-Tebar, Anabel; Gutiérrez, Fernanda; Ibarrola-Villava, Maider; Jiménez-Martí, Elena; Martínez-Lillo, José; Orts-Arroyo, Marta; Ribas, Gloria; Silvestre-Llora, Adriana [Journal of Inorganic Biochemistry, 2022, vol. 232]
[2]Castro, Isabel; Gil-Tebar, Anabel; Gutiérrez, Fernanda; Ibarrola-Villava, Maider; Jiménez-Martí, Elena; Martínez-Lillo, José; Orts-Arroyo, Marta; Ribas, Gloria; Silvestre-Llora, Adriana [Journal of Inorganic Biochemistry, 2022, vol. 232]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	61-19-8	MDL No. :	MFCD00005750
Formula :	C₁₀H₁₄N₅O₇P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UDMBCSSLTHHNCD-KQYNXXCUSA-N
M.W :	347.22	Pubchem ID :	6083
Synonyms :	5'-Adenylic acid;AMP;NSC 20264;Lycedan;Adenosine phosphate	Chemical Name :	((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate

Num. heavy atoms :	23
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.5
Num. rotatable bonds :	4
Num. H-bond acceptors :	10.0
Num. H-bond donors :	5.0
Molar Refractivity :	73.58
TPSA :	195.88 Å²

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-10.92 cm/s

Log Po/w (iLOGP) :	-0.1
Log Po/w (XLOGP3) :	-3.52
Log Po/w (WLOGP) :	-2.18
Log Po/w (MLOGP) :	-3.47
Log Po/w (SILICOS-IT) :	-3.53
Consensus Log Po/w :	-2.56

[ CAS No. 61-19-8 ] {[proInfo.proName]}

Quality Control of [ 61-19-8 ]

Related Doc. of [ 61-19-8 ]

Product Details of [ 61-19-8 ]

Calculated chemistry of [ 61-19-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 61-19-8 ]

Application In Synthesis of [ 61-19-8 ]

[ 61-19-8 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

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Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	1.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.11

Log S (ESOL) :	0.2
Solubility :	549.0 mg/ml ; 1.58 mol/l
Class :	Highly soluble
Log S (Ali) :	-0.01
Solubility :	338.0 mg/ml ; 0.973 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	1.26
Solubility :	6380.0 mg/ml ; 18.4 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	4.35

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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Physical hazards
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