[ CAS No. 305-84-0 ] {[proInfo.proName]}

Name: 305-84-0|(S)-2-(3-Aminopropanamido)-3-(1H-imidazol-5-yl)propanoic acid|98%
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Quality Control of [ 305-84-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 305-84-0 ]

SDS Specification

Alternatived Products of [ 305-84-0 ]

Product Details of [ 305-84-0 ]

CAS No. :	305-84-0	MDL No. :	MFCD00005207
Formula :	C₉H₁₄N₄O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CQOVPNPJLQNMDC-ZETCQYMHSA-N
M.W :	226.23	Pubchem ID :	439224
Synonyms :	L-Carnosine;NSC 524045;β-Alanylhistidine;Karnozin	Chemical Name :	(S)-2-(3-Aminopropanamido)-3-(1H-imidazol-5-yl)propanoic acid

Calculated chemistry of [ 305-84-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.44
Num. rotatable bonds :	7
Num. H-bond acceptors :	5.0
Num. H-bond donors :	4.0
Molar Refractivity :	55.07
TPSA :	121.1 Å²

Pharmacokinetics

GI absorption :	High
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) :	-10.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.21
Log Po/w (XLOGP3) :	-3.99
Log Po/w (WLOGP) :	-1.13
Log Po/w (MLOGP) :	-1.81
Log Po/w (SILICOS-IT) :	-0.21
Consensus Log Po/w :	-1.39

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	1.5
Solubility :	7180.0 mg/ml ; 31.8 mol/l
Class :	Highly soluble
Log S (Ali) :	2.05
Solubility :	25200.0 mg/ml ; 111.0 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-1.52
Solubility :	6.82 mg/ml ; 0.0301 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.63

Safety of [ 305-84-0 ]

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:

Applications of [ 305-84-0 ]

Carnosine (CAS: 305-84-0) is a dipeptide compound that acts as an antioxidant in biological systems. It scavenges free radicals and reactive oxygen species, thereby protecting cells and tissues from oxidative damage. Carnosine also helps buffer intracellular pH, maintaining the acid-base balance within cells.

Application In Synthesis of [ 305-84-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 305-84-0 ]
Downstream synthetic route of [ 305-84-0 ]

[ 305-84-0 ] Synthesis Path-Upstream 1~4

1
[ 3303-84-2 ]
[ 305-84-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: With trityl chloride polystyrene resin; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 0.5 h; Stage #2: With piperazine In dichloromethane; N,N-dimethyl-formamide for 1 h; Inert atmosphere	In the last step of the synthesis, peptide was cleaved from the resin with a mixture of TFA (1 mL), anizol(0.3 mL), phenol (0.3 g) and was shaken mechanically atroom temperature for 2 h. One important considerationwhen selecting the cleavage cocktail are scavengers, such asanizol, phenol, triisopropylsilane (TIPS), 1, 2-ethanedithiol(EDT), thioanisole or water. The reason the scavengers areoften added is because during the course of cleavage, highlyreactive cationic species can be generated, which can causedamage to the structure. The purpose of a scavenger is toextinguish any reactive species that may be generated duringrevelation from TFA cleavage. At the end of 2 h, the resin was filtered and washed with DMF (5 mL × 3) and after that with DCM (5 mL × 3). The filtrate was evaporated underreduced pressure and the resulting mixture precipitatedby adding diethylether (chemical formula = C9H14N4O3,molar mass = 226.23 g mol−1, melting point = 258 °C,yield = 90percent; Scheme 4). Boc is acid labile and sensitive toacid cleavage. A common process used to cleave the Boc offthe amine while on a solid phase resin is to add a solutionof 1:1 TFA in DCM (10 mL) at room temperature for 1 h.The amine will form a TFA salt and must be washed with3 successive steps of 1:1 DCM and DIPEA (10 mL g−1resin) to prepare the deprotected amine product for thenext addition step. If using 2-chlorotritylchloride resin, thiswill also cleave it, forming the resin as well as the amine.It is recommended to use a base labile resin if one needs toremove the Boc for further alkylation prior to deprotectionfrom a resin.15 (Yield = 90percent, melting point = 258 °C).Elemental analysis: calculated C (47.78percent), H (6.24percent),N (24.77percent), O (21.22percent). Molecular formula: C9H14N4O3;formula weight: 226.2324.

Reference： [1] Journal of the Brazilian Chemical Society, 2016, vol. 27, # 10, p. 1814 - 1819

2
[ 64017-81-8 ]
[ 7389-87-9 ]
[ 2140-53-6 ]
[ 1246364-63-5 ]
[ 1246364-64-6 ]
[ 305-84-0 ]

Reference： [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 2-3, p. 407 - 415

3
[ 64017-81-8 ]
[ 71-00-1 ]
[ 305-84-0 ]

Reference： [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 2-3, p. 407 - 415

4
[ 111196-17-9 ]
[ 71-00-1 ]
[ 305-84-0 ]

Reference： [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 2-3, p. 407 - 415

[ 305-84-0 ] Synthesis Path-Downstream 1~40

1
[ 305-84-0 ]
[ 125347-29-7 ]

Reference： [1]Bulletin de la Societe Chimique de France,1989,p. 88 - 94

2
[ 305-84-0 ]
[ 68808-73-1 ]
[ 39740-49-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 3302 - 3305

Yield	Reaction Conditions	Operation in experiment
		Plaque Cocktail, Part a (Dose):Taurine (10 g)HEPPS (1 g)Nicotinamide (500 mg)Carnosine (3 g)

4
[ 51908-29-3 ]
[ 305-84-0 ]
4-sulfamoylphenylthiourea-β-alanylhistidine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4884 - 4892

5
[ 75899-68-2 ]
[ 305-84-0 ]
(E)-(S)-2-(1-Hydroxy-hexyl)-8-oxo-1,5,9,13-tetraaza-bicyclo[10.2.1]pentadeca-4,12⁽¹⁵⁾,13-triene-10-carboxylic acid [ No CAS ]
N-(2-hydroxy-5-pentyltetrahydrofuran-yl)carnosine [ No CAS ]

Reference： [1]Journal of Mass Spectrometry,2002,vol. 37,p. 1219 - 1228

6
[ 305-84-0 ]
2^A,3^A-mannoepoxide-β-cyclodextrin [ No CAS ]
(2^AS,3^AR)-3^A-[(3-[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino}-3-oxopropyl)amino]-3^A-deoxy-β-cyclodextrin [ No CAS ]

Reference： [1]Helvetica Chimica Acta,2002,vol. 85,p. 1633 - 1643

7
[ 107-02-8 ]
[ 305-84-0 ]
(E)-(S)-8-Oxo-1,5,9,13-tetraaza-bicyclo[10.2.1]pentadeca-4,12⁽¹⁵⁾,13-triene-10-carboxylic acid [ No CAS ]
3-(1<i>H</i>-imidazol-4-yl)-2-[3-(3-oxo-propylamino)-propionylamino]-propionic acid [ No CAS ]
2-(3-amino-propionylamino)-3-[1-(3-oxo-propyl)-1<i>H</i>-imidazol-4-yl]-propionic acid [ No CAS ]
(E)-(S)-10-Carboxy-8-oxo-13-(3-oxo-propyl)-1,5,9-triaza-13-azonia-bicyclo[10.2.1]pentadeca-4,12⁽¹⁵⁾,13-triene [ No CAS ]

Reference： [1]Journal of Mass Spectrometry,2003,vol. 38,p. 996 - 1006

8
copper(II) nitrate [ No CAS ]
[ 305-84-0 ]
Cu⁽²⁺⁾*N₂C₃H₃CH₂CH(COO)NCOCH₂CH₂NH₂^(2-)={Cu(N₂C₃H₃CH₂CH(COO)NCOCH₂CH₂NH₂)} [ No CAS ]
2Cu⁽²⁺⁾*N₂C₃H₃CH₂CH(CO₂)NCOCH₂CH₂NH₂^(2-)={Cu₂(N₂C₃H₃CH₂CH(COO)NCOCH₂CH₂NH₂)}⁽²⁺⁾ [ No CAS ]
Cu⁽²⁺⁾*N₂C₃H₃CH₂CH(COOH)NHCOCH₂CH₂NH₂={Cu(N₂C₃H₃CH₂CH(COOH)NHCOCH₂CH₂NH₂)}⁽²⁺⁾ [ No CAS ]
Cu⁽²⁺⁾*N₂C₃H₃CH₂CH(COO)NHCOCH₂CH₂NH₂^(1-)={Cu(N₂C₃H₃CH₂CH(COO)NHCOCH₂CH₂NH₂)}⁽¹⁺⁾ [ No CAS ]
{Cu₂(N₂C₃H₃CH₂CH(COO)NCOCH₂CH₂NH₂)2} [ No CAS ]

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,1993,vol. 49,p. 1299 - 1306

9
[ 64017-81-8 ]
[ 7389-87-9 ]
[ 2140-53-6 ]
[ 1246364-63-5 ]
[ 1246364-64-6 ]
H-β-Ala-β-Ala-NH2 [ No CAS ]
[ 305-84-0 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 407 - 415

10
[ 64017-81-8 ]
[ 71-00-1 ]
[ 305-84-0 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 407 - 415

11
[ 111196-17-9 ]
[ 71-00-1 ]
[ 305-84-0 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 407 - 415

12
L-carnosine methyl ester [ No CAS ]
[ 305-84-0 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 407 - 415

13
[ 56-65-5 ]
[ 71-00-1 ]
[ 107-95-9 ]
[ 305-84-0 ]
[ 58-64-0 ]

Reference： [1]Journal of Biological Chemistry,2010,vol. 285,p. 9346 - 9356

14
[ 1284258-81-6 ]
[ 305-84-0 ]
[ 1284260-28-1 ]

Yield	Reaction Conditions	Operation in experiment
	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide;Inert atmosphere;	The reagents used for each of the amide bond formation was amino core (4 mumol), carboxylic acid (4 mumol, 1 eq.), DIEA (5 mumol, 1.2 eq.) and HBTU (4.5 mumol, 1.1eq.). A stock of the amino core for synthesis of 102 members requires an amount in excess of 150 fold. Both the starting amino core and the carboxylic acids were prepared as a stock solution of DMSO in a concentration of 0.6 mmol/1500 muL and 4 mumol/10 muL, respectively. HBTU and DIEA were dissolved in DMSO as a concentration of 4.5 mumol/10 muL (V/V) and 5 mumol/10 muL (V/V), respectively. Each of the acid portion was firstly mixed with the solution of HBTU in a plastic tube for 30 sec, followed by the addition of a mixture of the solution of amino core (4 mumol, 10 muL) and DIEA (10 muL) in a total volume of 40 muL. All vials were shaken for 1 min ultrasonically for the subsequent series dilution.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1320 - 1324

15
[ 84501-28-0 ]
[ 305-84-0 ]
C₃₀H₃₆N₈O₇^(2-)*2Na⁽¹⁺⁾ [ No CAS ]

Reference： [1]Synthetic Communications,2013,vol. 43,p. 345 - 360,16

16
[ 305-84-0 ]
(S)-S-((R)-2-acetamido-3-amino-3-oxopropyl)-2-(3-aminopropanamido)-3-(1H-imidazol-5-yl)propanethioate dihydrochloride [ No CAS ]

Reference： [1]Patent: WO2014/11624,2014,A2

17
[ 305-84-0 ]
[ 1538576-75-8 ]

Reference： [1]Patent: WO2014/11624,2014,A2

18
[ 305-84-0 ]
(R)-methyl 2-acetamido-3-(((S)-2-(3-aminopropanamido)-3-(1H-imidazol-5-yl)propanoyl)thio)propanoate dihydrochloride [ No CAS ]

Reference： [1]Patent: WO2014/11624,2014,A2

19
[ 305-84-0 ]
[ 1538576-76-9 ]

Reference： [1]Patent: WO2014/11624,2014,A2

20
[ 24424-99-5 ]
[ 305-84-0 ]
[ 405520-71-0 ]

Yield	Reaction Conditions	Operation in experiment
76%		To a stirring biphasic mixture of (S)-2-(3-aminopropanamido)-3-(lH-imidazol-5-yl)propanoic acid, L-Carnosine ( 25.0 g, 1 10.5 mmol) in 200 mL of dioxane and 200 mL of water containing NaOH (4.86 g, 121.51 mmol) at ~0 C under N2, was added dropwise a solution of di-ter/-butyl dicarbonate (53.1 g, 243.3 mmol) in 150 mL of dioxane. After allowing the solution to warm to room temperature overnight, the sample was acidified with the addition of 200 mL of saturated H2P04 solution, concentrated, then extracted with EtOAc (2 x 500 mL). The combined organic extracts were dried with MgSC , filtered and concentrated to give 35.74 g (76%) of 45c as white solid. MS (APCI) m/z 427 [M+H]+.

Reference： [1]Patent: WO2014/11624,2014,A2 .Location in patent: Paragraph 00141; 00142

21
[ 67-56-1 ]
[ 305-84-0 ]
methyl (2S)-2-[(3-aminopropanoyl)amino]-3-(4H-imidazol-4-yl)propanoate hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With thionyl chloride; for 1h;Reflux;	To a suspension of L-Carnosine (3g, 13.2 mmol) in dry MeOH (100 ml) cooled at 0C, SOCI2 (1.13ml, 15.6 mmol) was added dropwise and the mixture was stirred 10 minutes. The solution was then refluxed for 1 h and, after cooling to RT and the solvent was removed under reduced pressure. The product was triturated in DCM/MTBE 1/1 for 2 hours at rt, filtered and dried in vacuum to give the desired product in quantitative yield. MS: m z = 241 [M+H]+

Reference： [1]Patent: WO2016/34619,2016,A1 .Location in patent: Page/Page column 20-21

22
[ 305-84-0 ]
[ 78-98-8 ]
C₂₂H₂₉N₈O₆⁽¹⁺⁾ [ No CAS ]

Reference： [1]ChemMedChem,2016,p. 1778 - 1789

23
[ 131543-46-9 ]
[ 305-84-0 ]
C₁₁H₁₄N₄O₄ [ No CAS ]
C₂₂H₂₈N₈O₈ [ No CAS ]

Reference： [1]ChemMedChem,2016,p. 1778 - 1789

24
[ 100683-54-3 ]
[ 305-84-0 ]
C₁₂H₁₆N₄O₄ [ No CAS ]

Reference： [1]ChemMedChem,2016,p. 1778 - 1789

25
[ 850480-50-1 ]
[ 305-84-0 ]
C₁₈H₂₈N₄O₄ [ No CAS ]
N-(2-hydroxy-5-pentyltetrahydrofuran-yl)carnosine [ No CAS ]

Reference： [1]ChemMedChem,2016,p. 1778 - 1789

26
[ 3303-84-2 ]
N-9-fluorenylmethyloxycarbonyl-N-trityl-L-histidine [ No CAS ]
[ 305-84-0 ]

Yield	Reaction Conditions	Operation in experiment
90%		In the last step of the synthesis, peptide was cleaved from the resin with a mixture of TFA (1 mL), anizol(0.3 mL), phenol (0.3 g) and was shaken mechanically atroom temperature for 2 h. One important considerationwhen selecting the cleavage cocktail are scavengers, such asanizol, phenol, triisopropylsilane (TIPS), 1, 2-ethanedithiol(EDT), thioanisole or water. The reason the scavengers areoften added is because during the course of cleavage, highlyreactive cationic species can be generated, which can causedamage to the structure. The purpose of a scavenger is toextinguish any reactive species that may be generated duringrevelation from TFA cleavage. At the end of 2 h, the resin was filtered and washed with DMF (5 mL × 3) and after that with DCM (5 mL × 3). The filtrate was evaporated underreduced pressure and the resulting mixture precipitatedby adding diethylether (chemical formula = C9H14N4O3,molar mass = 226.23 g mol-1, melting point = 258 C,yield = 90%; Scheme 4). Boc is acid labile and sensitive toacid cleavage. A common process used to cleave the Boc offthe amine while on a solid phase resin is to add a solutionof 1:1 TFA in DCM (10 mL) at room temperature for 1 h.The amine will form a TFA salt and must be washed with3 successive steps of 1:1 DCM and DIPEA (10 mL g-1resin) to prepare the deprotected amine product for thenext addition step. If using 2-chlorotritylchloride resin, thiswill also cleave it, forming the resin as well as the amine.It is recommended to use a base labile resin if one needs toremove the Boc for further alkylation prior to deprotectionfrom a resin.15 (Yield = 90%, melting point = 258 C).Elemental analysis: calculated C (47.78%), H (6.24%),N (24.77%), O (21.22%). Molecular formula: C9H14N4O3;formula weight: 226.2324.

Reference： [1]Journal of the Brazilian Chemical Society,2016,vol. 27,p. 1814 - 1819

27
[ 2488-14-4 ]
[ 305-84-0 ]

Reference： [1]Synlett,2016,vol. 27,p. 2734 - 2736

28
[ 5970-45-6 ]
[ 305-84-0 ]
[ 107667-60-7 ]

Yield	Reaction Conditions	Operation in experiment
12.8 g	With sodium hydroxide; In methanol; at 50 - 60℃; for 1h;	In a 500 ml three-necked flask, 100 ml of methanol,9.71 g of zinc acetate dihydrate, 10 g of L-<strong>[305-84-0]carnosine</strong> was added and suspended,And gradually heated to maintain the temperature at 60 C. 3.52 g of sodium hydroxide was completely dissolved in 70 ml of methanol,Sodium hydroxide solution was prepared,Was slowly added to the suspension.The reaction solution was stirred at 50 to 60 DEG CAfter stirring for 1 hour,Cooled to 30 & lt; 0 & gt; C, and 80 ml of purified water was gradually added dropwise for 30 minutes. After the addition of purified water, the mixture was stirred at the same temperature for 1 hour,Filtered under reduced pressure, washed sequentially with 80 ml of purified water and 80 ml of methanol,12.8 g of a white powdery crystal was obtained.NMR analysis of the white powdery crystal revealed that the content of sodium acetate was 0.5% by weight.

Reference： [1]Patent: KR2017/23417,2017,A .Location in patent: Paragraph 0021; 0022

29
[ 305-84-0 ]
L-5-sulfanylcarnosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%	With hydrogenchloride; N-Bromosuccinimide; tiolacetic acid; In water; at 0℃; for 1h;	L-Carnosine (425 mg; 1.88 mmoles; 1 eq.) is dissolved in 12 mL of demineralized water containing a 37% concentrated hydrochloric acid solution (370 mg; 3.75 mmoles; 2 eq.), then the solution is cooled to 0 C. N-Bromosuccinimide (440 mg; 2.44 mmoles; 1.3 eq.) is added in one portion: the solution turns limpid orange. Thioacetic acid (960 muL; 1.03 g, 13.14 mmoles; 7 eq.) is added. The mixture is stirred at 0 C. for 1 h. The solution is extracted with 4 times 12 mL of ethyl acetate. After neutralization and purification on silica in the presence of dithiothreitol (290 mg; 1.88 mmoles; 1 eq.), L-5-sulfanyl<strong>[305-84-0]carnosine</strong> (Compound 30) (70 mg; 14%; 22% with respect to the quantity of the intermediate SAc) is obtained in the form of a colorless lacquer.1H NMR (D2O, 400 MHz): delta (ppm)=2.69 (t, J=6.7 Hz, 2H); 3.00 (m, 1H); 3.12 (m, 1H); 3.23 (t, J=6.7 Hz, 2H); 4.43 (dd, J=8.5 Hz, J=4.2 Hz, 1H); 8.20 (s, 1H).LCMS (APO): 259.1 [M+H]+

Reference： [1]Patent: US2017/190691,2017,A1 .Location in patent: Paragraph 0293; 0294; 0295; 0296

30
[ 50-99-7 ]
[ 305-84-0 ]
1-deoxy-D-fructosyl-N-β-alanyl-L-histidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With Sucrose In water at 60℃; for 2h;	5 Example 5: Preparation of 1-deoxy-D-fructosyl-N-β-alanyl-L-histidine from Glucose and Carnosine (8-alanyl-L-histidine) in a Liquid Eutectic Mixture [Glucose/Sucrose] at Different Heating Times Preparation of liquid eutectic mixture from glucose and sucrose: 5.0 g glucose (28 mmol) and 9.5 g sucrose (28 mmol) were dissolved in 30 mL water. The resulting solution was then concentrated under reduced pressure at 50° C. to give a liquid eutectic mixture consisting of glucose and sucrose at a molar ratio of 50/50 with 9.93% H2O. Sniffing the liquid eutectic mixture confirmed that there had been no change in aroma during the process of forming the liquid eutectic mixture. 150 mg carnosine (0.664 mmol) was added to 14.50 g of liquid eutectic mixture of glucose/sucrose (molar ratio 50/50, 9.93% H2O) and the resulting mixture was heated for 1, 2 or 6 hours at 60° C. Quantification of 1-Deoxy-D-fructosyl-N-β-alanyl-L-histidine was performed as described in Example 2. Influence of the heating time on the yield of 1-deoxy-D-fructosyl-N-β-alanyl-L-histidine is shown in FIG. 5. A yield of 71% was obtained after a heating time of 2 hours. It can be seen that reacting glucose and carnosine in a liquid eutectic mixture results in a higher yield of 1-deoxy-D-fructosyl-N-β-alanyl-L-histidine than when glucose and carnosine are reacted in a methanol/glycerol solvent (Example 1). The reaction in a liquid eutectic mixture results in yields of 1-deoxy-D-fructosyl-N-β-alanyl-L-histidine more than an order of magnitude greater than when glucose and carnosine are reacted in aqueous systems (Examples 2, 3 and 4).

Reference： [1]Current Patent Assignee: NESTLE S.A. - US2018/55078, 2018, A1 Location in patent: Paragraph 0033-0047

31
[ 305-84-0 ]
C₉H₁₄N₄O₃⁽¹⁸⁾O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(II) sulfate; ascorbic acid; oxygen-18; In aq. phosphate buffer; at 20℃; for 0.0833333h;pH 7.2;	Oxidation of the imidazole ring of the IDPs was carried outby the ascorbic acid-copper ion system (12). The reaction mix-tures (5 ml) containing 10 m M IDPs, 200 m M sodium phosphatebuffer (pH 7.2), 200 m M ascorbate, and 2 m M CuSO 4 were incu-bated at room temperature. Oxygen gas was bubbled into themixture for 30 min. The oxidized IDPs were purified under thefollowing conditions: a Scherzo SS-C18 column (6.0 100mm) using a linear gradient of solvent A (water containing 0.1%formic acid) and solvent B (water containing 50% acetonitrileand 100 m M ammonium formate) (0% B at 0 min; 90% B at 20min) at the flow rate of 1.5 ml/min. The elution was monitoredby absorbance at 250 nm. The chemical structures of the prod-ucts were characterized by LC-ESI-MS/MS and NMR analy-sis. The NMR analyses were performed using a JEOL JNM-ECZ500R (500 MHz) instrument. 2-Oxo-<strong>[305-84-0]carnosine</strong>:1H NMR(D 2 O):H2.54(dt,J 3.5 Hz, 2H), 2.66 (dd, J 8.2 Hz, 1H),2.80 (dd, J 5.5 Hz, 1H), 3.06 (t, J 6.8 Hz, 2H), 4.41 (dd, J 4.7Hz, 1H), 6.12 (s, 1H);C31.34,35.83,39.70,56.61,119.01,132.18, 159.10, 176.06, 179.17. 2-Oxo-anserine:1H NMR(D 2 O):H2.26(dt,J 3.1 Hz, 2H), 2.60 (dd, J 10 Hz, 1H),2.70 (t, J 6.5 Hz, 2H), 2.84 (m, 1H), 3.05 (s, 3H), 4.26 (dd, J 4.7 Hz, 1H), 6.12 (s, 1H);C29.10,31.92,37.67,38.87,55.07,117.95, 129.67, 155.86, 175.47, 179.10. 2-Oxo-homo<strong>[305-84-0]carnosine</strong>:1H NMR (D 2 O):H1.72-1.75(m,2H),2.21(dt,J 3.5 Hz, 2H),2.53 (dd, J 8.2 Hz, 1H), 2.76-2.81 (m, 3H), 4.23 (dd, J 4.7Hz, 1H), 6.08 (S, 1H);C24.41,29.46,33.86,40.21,55.46,116.34, 129.51, 164.25, 175.61, 178.91.

Reference： [1]Journal of Biological Chemistry,2019,vol. 294,p. 1279 - 1289

32
[ 305-84-0 ]
C₉H₁₄N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With oxygen; copper(II) sulfate; ascorbic acid; In aq. phosphate buffer; at 20℃; for 0.5h;pH 7.2;	Oxidation of the imidazole ring of the IDPs was carried outby the ascorbic acid-copper ion system (12). The reaction mix-tures (5 ml) containing 10 m M IDPs, 200 m M sodium phosphatebuffer (pH 7.2), 200 m M ascorbate, and 2 m M CuSO 4 were incu-bated at room temperature. Oxygen gas was bubbled into themixture for 30 min. The oxidized IDPs were purified under thefollowing conditions: a Scherzo SS-C18 column (6.0 100mm) using a linear gradient of solvent A (water containing 0.1%formic acid) and solvent B (water containing 50% acetonitrileand 100 m M ammonium formate) (0% B at 0 min; 90% B at 20min) at the flow rate of 1.5 ml/min. The elution was monitoredby absorbance at 250 nm. The chemical structures of the prod-ucts were characterized by LC-ESI-MS/MS and NMR analy-sis. The NMR analyses were performed using a JEOL JNM-ECZ500R (500 MHz) instrument. 2-Oxo-<strong>[305-84-0]carnosine</strong>:1H NMR(D 2 O):H2.54(dt,J 3.5 Hz, 2H), 2.66 (dd, J 8.2 Hz, 1H),2.80 (dd, J 5.5 Hz, 1H), 3.06 (t, J 6.8 Hz, 2H), 4.41 (dd, J 4.7Hz, 1H), 6.12 (s, 1H);C31.34,35.83,39.70,56.61,119.01,132.18, 159.10, 176.06, 179.17. 2-Oxo-anserine:1H NMR(D 2 O):H2.26(dt,J 3.1 Hz, 2H), 2.60 (dd, J 10 Hz, 1H),2.70 (t, J 6.5 Hz, 2H), 2.84 (m, 1H), 3.05 (s, 3H), 4.26 (dd, J 4.7 Hz, 1H), 6.12 (s, 1H);C29.10,31.92,37.67,38.87,55.07,117.95, 129.67, 155.86, 175.47, 179.10. 2-Oxo-homo<strong>[305-84-0]carnosine</strong>:1H NMR (D 2 O):H1.72-1.75(m,2H),2.21(dt,J 3.5 Hz, 2H),2.53 (dd, J 8.2 Hz, 1H), 2.76-2.81 (m, 3H), 4.23 (dd, J 4.7Hz, 1H), 6.08 (S, 1H);C24.41,29.46,33.86,40.21,55.46,116.34, 129.51, 164.25, 175.61, 178.91.

Reference： [1]Journal of Biological Chemistry,2019,vol. 294,p. 1279 - 1289

33
[ 14691-88-4 ]
[ 305-84-0 ]
C₁₈H₃₂N₆O₄ [ No CAS ]
C₉H₁₄N₄O₄ [ No CAS ]

Reference： [1]Journal of Biological Chemistry,2019,vol. 294,p. 1279 - 1289

34
[ 1236199-60-2 ]
[ 305-84-0 ]
C₂₈H₄₁ClN₈O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In aq. buffer; at 37℃;pH 7.3;	General procedure: <strong>[1236199-60-2]NL-101</strong> (0.03 g) was incubated with amino acids (0.02 g) and peptides (0.03 g) at 37 oC in a buffer solution, which pH was 5.3,7.3 and 9.3 respectively as the experimental surroundings. The pH of the samples was determined by a pH-meter (FE 20, MettlerToledo). All samples were kept at -20 oC until further analysis. The desalting step of the <strong>[1236199-60-2]NL-101</strong> adducts obtained under theexperimental conditions was not carried out before MS analysis.

Reference： [1]Chinese Chemical Letters,2018

35
[ 305-84-0 ]
[ 40846-94-4 ]
[ 1313499-16-9 ]

Reference： [1]Biochemistry (Moscow) Supplement Series B: Biomedical Chemistry,2018,vol. 12,p. 308 - 315

36
[ 79-63-0 ]
[ 305-84-0 ]
L-carnosine lanosteryl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In chloroform; for 4h;Reflux;	A 100-mL round-bottomed flask was charged with L-<strong>[305-84-0]carnosine</strong> (1 .41 g, 6.2 mmol), chloroform (CHC , 40 mL), lanosterol (3.2 g, 7.5 mmol) and p-toluenesulfonic acid (3.5 g, 18.8 mmol). The suspension was heated at reflux, and H2O, which is formed during the reaction, was removed by continuous azeotropic distillation. The distillation temperature was progressively increased and the starting suspension became a solution. After 4 h, the reaction was complete. The solvent was evaporated in vacuo, and the residue was dissolved in MeOH and passed through an ion exchange column to remove p-toluenesulfonic acid. The collected solution was evaporated in vacuo to yield L-<strong>[305-84-0]carnosine</strong> lanosteryl ester as a white solid.

Reference： [1]Patent: WO2019/97434,2019,A1 .Location in patent: Paragraph 00120-00122

37
Smoc-β-alanine [ No CAS ]
[ 71-00-1 ]
[ 305-84-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-hydroxy-pyrrolidine-2,5-dione; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In water; acetonitrile; at 4℃; for 0.2h;pH 7.5;	Smoc--alanine is added to an ion exchange resin (DEAE Sephadex A-25; GE Healthcare) at a maximum load. Smoc--alanine is activated by 3 equivalents 1 - ethyl-3-(3-dimethylaminopropyl)carbodiimid (EDC) and 2 equivalents N- hydroxysuccinimide (NHS) in mixture of water and acetonitrile (MeCN) 4:1 ratio (volume). The activation was much higher than in Example 4. Thereafter the ion exchanger loaded with the activated Smoc--alanine is washed two times with water. After the washing step, 1 .5 equivalents L-histidine solved in water are added to the activated Smoc--alanine and reacted at 4C for 12 minutes at pH 7.5 under agitation. Excess of L-histidine and released NHS are removed by washing with water. The yield in Example 5 is higher than the yield in Example 4. The formed L-carnosine is released by deprotection using 0.25 mM NaOH (pH 10, 10 minutes) or Na2C03 (pH 10, 20 minutes).The formed L-carnosine is released by deprotection using 0.25 mM NaOH (pH 10, 10 minutes) or Na2C03 (pH 10, 20 minutes).

Reference： [1]Patent: WO2019/101940,2019,A1 .Location in patent: Page/Page column 60-61; 63-64

38
4-(((L-histidyl)oxy)methyl)-N,N,N-trimethylbenzenaminium [ No CAS ]
Smoc-β-alanine [ No CAS ]
[ 305-84-0 ]

Reference： [1]Patent: WO2019/101940,2019,A1 .Location in patent: Page/Page column 73

39
C₅₉H₉₀N₄O₇ [ No CAS ]
[ 305-84-0 ]
C₆₄H₉₉N₇O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		General procedure: 1 mL NaHCO3 aqueous solution with 66 mg (0.62 mmol) was added into the 5 mL DMF solution with 37 mg (0.21 mmol) L-arginine.This solution was stirred 30 min, and then 0.1 g (0.1 mmol) Py3-NHS DMF solution was added drop-wisely into the reaction. It was stirred overnight and then adjusted with the equally HCl aqueous solution. The mixture was extracted with CH2Cl2 three times and organic phase was collected. Anhydrous Na2SO4 was used to dry the organic extract. The crude product was purified by a silica column with CH2Cl2/MeOH 10:1 as eluent (Yield: 63%).

Reference： [1]Chinese Chemical Letters,2020,vol. 31,p. 885 - 889

40
[ 1025967-78-5 ]
[ 305-84-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
85.4%	In water at 20 - 25℃; for 1h;	2 Preparation of lifitegrast carnosine salt 18 mL of water and 345 mg of carnosine were added to a vessel equipped with a magnetic stirrer at room temperature (20-25°C) and mixed for 10 minutes. To the mixture, 960 mg of lifitegrast was then added. The mixture was stirred for 60 minutes (until the solution was clear) and was then filtered and evaporated to dryness.Preparation of amorphous lifitegrast carnosine salt (method I)Lifitegrast carnosine salt (438 mg) was added to 96% ethanol (3 mL). The mixture was heated to 60- 65°C and stirred for 60 minutes at this temperature. The solution was then cooled to 5-8°C. The resulting white precipitate was removed by filtration, washed with cold absolute ethanol, and dried to provide amorphous lifitegrast carnosine salt (85.4% yield). The PXRD of the dried carnosine salt was recorded confirming amorphous form of salt (see Figure 1 , Lif_Car_A).

Reference： [1]Current Patent Assignee: WARSZAWSKIE ZAKL FARMACEUTYCZNE POLFA - WO2021/130168, 2021, A1 Location in patent: Page/Page column 11-12

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Technical Information

• Acids Combine with Acyl Halides to Produce Anhydrides • Acyl Chloride Hydrolysis • Amide Hydrolysis • Amide Hydrolysis • Anhydride Hydrolysis • Arndt-Eistert Homologation • Carbonation of Organometallics • Carboxylate Salt Formation • Carboxylic Acids React with Alcohols to Form Esters • Decarboxylation of Substituted Propanedioic • Deprotection of Cbz-Amino Acids • Esters Hydrolyze to Carboxylic Acids and Alcohols • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Hunsdiecker-Borodin Reaction • Nitriles Hydrolyze to Carboxylic Acids • Oxidation of Aldehydes Furnishes Carboxylic Acids • Oxidation of Primary Alcohols Furnishes Carboxylic Acids • Passerini Reaction • Peptide Bond Formation with DCC • Periodic Acid Degradation of Sugars • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Carboxylic Acids • Reduction of Carboxylic Acids by LiAlH4 • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • The Conversion of Carboxylic Acids into Acyl Halides • Ugi Reaction

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[ 305-84-0 ]

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H200	Unstable explosive
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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