Home Cart 0 Sign in  

[ CAS No. 113-24-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 113-24-6
Chemical Structure| 113-24-6
Structure of 113-24-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 113-24-6 ]

Related Doc. of [ 113-24-6 ]

Alternatived Products of [ 113-24-6 ]

Product Details of [ 113-24-6 ]

CAS No. :113-24-6 MDL No. :MFCD00002586
Formula : C3H3NaO3 Boiling Point : -
Linear Structure Formula :- InChI Key :DAEPDZWVDSPTHF-UHFFFAOYSA-M
M.W :110.04 Pubchem ID :23662274
Synonyms :
Sodium 2-oxopropanoate

Calculated chemistry of [ 113-24-6 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.33
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 16.56
TPSA : 57.2 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : -18.51
Log Po/w (XLOGP3) : -0.33
Log Po/w (WLOGP) : -1.67
Log Po/w (MLOGP) : -0.96
Log Po/w (SILICOS-IT) : -0.48
Consensus Log Po/w : -4.39

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.25
Solubility : 62.1 mg/ml ; 0.564 mol/l
Class : Very soluble
Log S (Ali) : -0.41
Solubility : 42.8 mg/ml ; 0.389 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.51
Solubility : 358.0 mg/ml ; 3.25 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 113-24-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 113-24-6 ]

* 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.

  • Downstream synthetic route of [ 113-24-6 ]

[ 113-24-6 ] Synthesis Path-Downstream   1~81

  • 1
  • [ 453-17-8 ]
  • [ 113-24-6 ]
  • (2R,4R,5R)-2,4,5-Trihydroxy-tetrahydro-pyran-2-carboxylic acid; compound with ammonia [ No CAS ]
  • 2
  • [ 453-17-8 ]
  • [ 113-24-6 ]
  • [ 60299-43-6 ]
  • 3
  • [ 497-09-6 ]
  • [ 113-24-6 ]
  • (2R,4R,5S)-2,4,5-Trihydroxy-tetrahydro-pyran-2-carboxylic acid; compound with ammonia [ No CAS ]
  • 4
  • [ 21593-77-1 ]
  • [ 2179-57-9 ]
  • [ 539-86-6 ]
  • [ 29418-05-1 ]
  • [ 113-24-6 ]
  • 5
  • [ 154-17-6 ]
  • [ 113-24-6 ]
  • [ 75003-84-8 ]
  • 6
  • [ 3615-17-6 ]
  • [ 113-24-6 ]
  • N-acetyl neuraminic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
42.6% With sodium azide; potassium phosphate buffer In water at 25℃; for 48h; pH 7.5, sialic acid aldolase (EC 4.1.3.3, from Escherichia coli);
  • 7
  • [ 15753-50-1 ]
  • [ 113-24-6 ]
  • [ 89395-29-9 ]
  • 8
  • [ 304-20-1 ]
  • [ 113-24-6 ]
  • [ 67536-13-4 ]
  • 9
  • [ 113-24-6 ]
  • [ 524-36-7 ]
  • C11H12N2O4(2-) [ No CAS ]
  • 10
  • [ 154-17-6 ]
  • [ 113-24-6 ]
  • (4R,6R)-3,5-dideoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]hex-2-ulopyranosonic acid [ No CAS ]
  • 12
  • [ 453-17-8 ]
  • [ 113-24-6 ]
  • sodium 2-dehydro-3-deoxy-D-gluconate [ No CAS ]
  • 13
  • [ 453-17-8 ]
  • [ 113-24-6 ]
  • [ 142937-56-2 ]
  • [ 60299-43-6 ]
  • 14
  • [ 453-17-8 ]
  • [ 113-24-6 ]
  • [ 108-24-7 ]
  • [ 90044-39-6 ]
  • [ 148130-14-7 ]
  • 15
  • [ 113-24-6 ]
  • [ 42373-30-8 ]
  • [ 197507-59-8 ]
  • 16
  • [ 113-24-6 ]
  • [ 55279-29-3 ]
  • [ 316155-87-0 ]
  • 17
  • [ 453-17-8 ]
  • [ 113-24-6 ]
  • [ 56742-44-0 ]
  • [ 17510-99-5 ]
  • 18
  • [ 497-09-6 ]
  • [ 113-24-6 ]
  • 3-deoxy-L-threo-2-hexulosonic acid [ No CAS ]
  • (4R,5S)-3-deoxy-2-hexulosonic acid [ No CAS ]
  • 19
  • [ 530-26-7 ]
  • [ 113-24-6 ]
  • [ 3150-24-1 ]
  • 4-nitrophenyl O-(3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranose [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tPm0188Ph; cytidine triphosphate; magnesium chloride In various solvents at 37℃; for 2h;
  • 20
  • [ 2268-15-7 ]
  • [ 113-24-6 ]
  • [ 182756-63-4 ]
  • 22
  • [ 1794-45-2 ]
  • [ 113-24-6 ]
  • [ 939810-20-5 ]
  • 23
  • [ 304-20-1 ]
  • [ 113-24-6 ]
  • 1-hydrazinophthalazine pyruvate hydrazone [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% EXAMPLE 7 Preparation of 1-hydrazinophthalazine Pyruvate Hydrazone (a) 1-hydrazinophthalazine HCL (5 g; 25 mmoles) is dissolved in 50 ml 0.1 M sodium phosphate buffer pH 7.4, and a solution of sodium pyruvate (11 g; 100 mmoles) in 30 ml of 0.1 M sodium phosphate buffer pH 7.4 is added while stirring vigorously. The solution becomes distinctively yellow almost immediately and the hydrazone is precipitated slowly. After standing overnight at 4 C., the yellow crystalline product is filtered off and washed with cold distilled water. The residue is recrystallized from hot ethanol-water to yield 4.3 g of 1-hydrazinophthalazine pyruvate hydrazone (70% of theoretical yield). [Journal of Chromatography 187:171-179 (1980)]
70% EXAMPLE 7 Preparation of 1-hydrazinophthalazine pyruvate hydrazone (a) 1-hydrazinophthalazine HCL (5 g; 25 mmoles) is dissolved in 50 ml 0.1 M sodium phosphate buffer pH 7.4, and a solution of sodium pyruvate (11 g; 100 mmoles) in 30 ml of 0.1 M sodium phosphate buffer pH 7.4 is added while stirring vigorously. The solution becomes distinctively yellow almost immediately and the hydrazone is precipitated slowly. After standing overnight at 4 C., the yellow crystalline product is filtered off and washed with cold distilled water. The residue is recrystallized from hot ethanol-water to yield 4.3 g of 1-hydrazinophthalazine pyruvate hydrazone (70% of theoretical yield). [Journal of Chromatography 187:171-179 (1980)].
  • 24
  • [ 113-24-6 ]
  • [ 40918-51-2 ]
  • [ 82834-12-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;palladium-carbon; In tetrahydrofuran; ethanol; at 40℃; under 22502.3 Torr; for 40.5h;Heating / reflux;Product distribution / selectivity; L-norvaline ethyl ester hydrochloride (50 g), 300 ml of ethanol and pyruvic acid sodium salt (31.8 g) were hydrogenated in the presence of 5 g of 7.5 % Pd/C (dry basis) for 40 h at 40 C and at a pressure of 3 MPa. Then, the mixture was filtered to remove the catalyst and sodium chloride. The filtrate was evaporated to dryness. 300 ml of THF were added and the mixture was heated to reflux for 30 minutes and then filtered. 45 ml of water were added to the clear filtrate and the solution was cooled to 10 C for crystallization. The obtained solid was collected and dried at 70 C for 6 h to give 24 g of N-((S)-1-carbethoxybutyl)-(S)-alanine (HPLC: 92.4%; R-isomer, i.e. N-((S)-1-carbethoxybutyl)-(R)-alanine: 1.7%). This solid was again purified with THF and water as described above to obtain 19 g of the title compound (HPLC: 94.6%; R-isomer: 0.8%; optical rotation: +3.1).
With hydrogen;palladium-carbon; In tetrahydrofuran; ethanol; water; at 40℃; under 22502.3 Torr; for 10.5h;Heating / reflux;Product distribution / selectivity; L-norvaline ethyl ester hydrochloride (50 g), 280 ml of 95 % ethanol and pyruvic acid sodium salt (31.8 g) were hydrogenated in the presence of 5 g of 7.5 % Pd/C (dry basis) for 10 h at 40 C and at a pressure of 3 MPa. Then, the mixture was filtered to remove the catalyst and sodium chloride. The filtrate was evaporated to dryness. 350 ml of THF were added and the mixture was heated to reflux for 30 minutes and then filtered to remove sodium chloride. The filtrate was cooled to 10 C for crystallization. The obtained solid was collected and dried to give 34 g of N-((S)-1-carbethoxybutyl)-(S)-alanine (HPLC: 91.4%; R-isomer: 1.8%). This solid was purified with THF again as described above to obtain 24 g of the title compound (HPLC: 97.6%; R-isomer: 0.48%; optical rotation: +2.78).
  • 25
  • [ 10025-99-7 ]
  • [ 113-24-6 ]
  • [ 1738-76-7 ]
  • [ 98798-30-2 ]
  • 26
  • potassium tetrachloroplatinate [ No CAS ]
  • [ 113-24-6 ]
  • [ 42303-42-4 ]
  • [ 99127-10-3 ]
  • 27
  • [ 113-24-6 ]
  • [ 42303-42-4 ]
  • nickel(II) hydroxide [ No CAS ]
  • [ 99127-11-4 ]
  • 28
  • [ 113-24-6 ]
  • [ 42303-42-4 ]
  • [ 20427-59-2 ]
  • [ 99127-12-5 ]
  • 29
  • potassium tetrachloroplatinate [ No CAS ]
  • [ 22059-21-8 ]
  • [ 113-24-6 ]
  • [ 99127-09-0 ]
  • 30
  • [ 12128-23-3 ]
  • [ 113-24-6 ]
  • [ 524-36-7 ]
  • [ 62914-46-9 ]
  • 31
  • [ 52462-29-0 ]
  • [ 113-24-6 ]
  • [ 22838-46-6 ]
  • [ 355023-67-5 ]
  • 32
  • [ 10025-74-8 ]
  • [ 113-24-6 ]
  • [ 212697-43-3 ]
  • [Dy(C2H4)3N3(C2H4NC(CH3)CO2)3]*3NaCl*2H2O [ No CAS ]
  • 33
  • N-methoxyacetate-D-mannosamine [ No CAS ]
  • [ 113-24-6 ]
  • [ 3150-24-1 ]
  • 4-nitrophenyl O-[5-(2-methoxyacetamido)-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid]-(2->3)-O-β-D-galactopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida sialyltransferase 1; Pasturella multocida sialic acid aldolase; magnesium chloride; cytidine 5'-triphosphate disodium salt In water at 37℃; aq. Tris-HCl buffer; Enzymatic reaction;
  • 34
  • N-methoxyacetate-D-mannosamine [ No CAS ]
  • [ 113-24-6 ]
  • [ 3150-24-1 ]
  • 4-nitrophenyl O-[5-(2-methoxyacetamido)-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid]-(2->6)-O-β-D-galactopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With Neisseria meningitidis CMP-sialic acid synthetase; Pasturella multocida sialic acid aldolase; Photobacterium damsela α2-6-sialyltransferase; magnesium chloride; cytidine 5'-triphosphate disodium salt In water at 37℃; aq. Tris-HCl buffer; Enzymatic reaction;
  • 35
  • [ 113-24-6 ]
  • [ 97604-58-5 ]
  • [ 3150-24-1 ]
  • 4-nitrophenyl O-[5-azido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid]-(2->3)-O-β-D-galactopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida sialyltransferase 1; Pasturella multocida sialic acid aldolase; magnesium chloride; cytidine 5'-triphosphate disodium salt In water at 37℃; aq. Tris-HCl buffer; Enzymatic reaction;
  • 36
  • [ 113-24-6 ]
  • [ 97604-58-5 ]
  • [ 3150-24-1 ]
  • 4-nitrophenyl O-[5-azido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid]-(2->6)-O-β-D-galactopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With Neisseria meningitidis CMP-sialic acid synthetase; Pasturella multocida sialic acid aldolase; Photobacterium damsela α2-6-sialyltransferase; magnesium chloride; cytidine 5'-triphosphate disodium salt In water at 37℃; aq. Tris-HCl buffer; Enzymatic reaction;
  • 37
  • [ 113-24-6 ]
  • 2-deoxy-2-(fluoroacetamido)-D-mannose [ No CAS ]
  • [ 3150-24-1 ]
  • 4-nitrophenyl O-[5-(2-fluoroacetamido)-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid]-(2->3)-O-β-D-galactopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida sialyltransferase 1; Pasturella multocida sialic acid aldolase; magnesium chloride; cytidine 5'-triphosphate disodium salt In water at 37℃; aq. Tris-HCl buffer; Enzymatic reaction;
  • 38
  • [ 113-24-6 ]
  • [ 20577-61-1 ]
  • ethyl 3-hydroxy-3-methyl-4-oxopentanoate [ No CAS ]
  • ethyl 3-hydroxy-3-methyl-4-oxopentanoate [ No CAS ]
  • 39
  • [ 367-12-4 ]
  • [ 113-24-6 ]
  • [ 7423-96-3 ]
  • 40
  • [ 6296-89-5 ]
  • [ 113-24-6 ]
  • C11H12N2O4 [ No CAS ]
  • 41
  • [ 113-24-6 ]
  • [ 2243-58-5 ]
  • [ 42178-83-6 ]
  • 42
  • [ 10025-74-8 ]
  • [ 113-24-6 ]
  • [ 7732-18-5 ]
  • Dy(pyruvate)3*3.5H2O [ No CAS ]
  • 43
  • [ 1080-12-2 ]
  • [ 113-24-6 ]
  • [ 1073529-13-1 ]
  • 44
  • [ 6326-79-0 ]
  • [ 113-24-6 ]
  • [ 31009-04-8 ]
  • 45
  • [ 317-20-4 ]
  • [ 113-24-6 ]
  • 8-fluoroquinoline-4-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With sodium hydroxide; In water; at 110℃; for 0.166667h;Microwave irradiation; Preparation 5. Synthesis of 8-F-4-CO2H-quinoline: To a solution of <strong>[317-20-4]7-fluoroisatin</strong> (500 mg, 3.03 mmol) in water (10 mL) at the room temperature were added aqueous NaOH solution (2.5 mL, SM, 12.5 mmol) and sodium pyruvate (400 mg, 3.66 mmol), and it?s then placed in a microwavereactor (CEM discover 5) at 110C for 10 mm. The resulting solution was cooled down and acidified to pH 2, and the dark solid was then collected. A suspension ofsolid in water (2 mL) was then placed in a 10 mL microwave tube followed by stirring at 170C (or 280 psi) in a microwave reactor for 5 mm. The desired product (brown solid, 340 mg, 60% yield) was then filtered off and collected. LRMS (M+Hj m/z: cacld 192.04, found 192.16.
  • 46
  • [ 346-34-9 ]
  • [ 113-24-6 ]
  • [ 1219834-23-7 ]
  • 47
  • [ 346-34-9 ]
  • [ 113-24-6 ]
  • 5-fluoroquinoline-2,4-dicarboxylic acid [ No CAS ]
  • 48
  • [ 20780-72-7 ]
  • [ 113-24-6 ]
  • [ 1219834-22-6 ]
  • 50
  • [ 39755-95-8 ]
  • [ 113-24-6 ]
  • [ 86-68-0 ]
  • 51
  • [ 84575-27-9 ]
  • [ 113-24-6 ]
  • [ 1092288-64-6 ]
  • 52
  • [ 84575-27-9 ]
  • [ 113-24-6 ]
  • 8-methoxy-quinoline-2,4-dicarboxylic acid [ No CAS ]
  • 53
  • [ 113-24-6 ]
  • [ 87-48-9 ]
  • [ 160233-76-1 ]
  • 54
  • [ 113-24-6 ]
  • 5-ethoxy-indol-2,3-dione [ No CAS ]
  • [ 525-39-3 ]
  • 55
  • [ 3615-17-6 ]
  • [ 1448670-81-2 ]
  • [ 113-24-6 ]
  • C66H97N15O26S [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With Escherichia coli sialic acid aldolase; Neisseria meningitidis cytidine 5′-triphosphate-sialic acid synthetase; Photobacterium damselae α2–6-sialyltransferase; cytidine triphosphate; magnesium chloride In aq. buffer at 37℃; for 16h; Enzymatic reaction; 4.6 One-pot three-enzyme synthesis of STn-MUC1 glycopeptides APG(Siaα2-6GalNAcα)STAPPA General procedure: Tn-MUC1 glycopeptide 2 (4mg, 3μmol, 1.0 equiv), sodium pyruvate (5 equiv), and CTP (2 equiv) were dissolved in water and in a 0.5mL centrifuge tube containing Tris-HCl buffer (100mM, pH 8.5) and MgCl2 (20mM). The resulting mixture was split equally to 4 tubes and ManNAc or its derivative (1.5equiv) was added to each tube. After the addition of EcNanA (25μg/mL), NmCSS (30μg/mL), and Pd2, 6ST (50μg/mL), ddH2O was added to bring the volume of the reaction mixture to 300μL. The reaction mixture was incubated at 37°C for 6h with shaking (140 rpm). Additional CTP (1equiv) was added and the reaction was continued for 10h. The product formation was monitored by thin-layer chromatography (TLC) developed with EtOAc/MeOH/H2O/HOAc (4:2:1:0.2) as the developing solvent. After TLC indication that the reaction reached 90% yield, the reaction mixture was loaded to a C18 cartridge for flash purification. The cartridge was washed six times with 1mL of water each time and the glycopeptide was eluted with 2mL of methanol and dried using SpeedVap concentrator. The obtained glycopeptide mixture was subjected to another round of OPME reaction to allow the complete consumption of the Tn-MUC1 glycopeptide acceptor. The resulting STn-MUC1 glycopeptides were dissolved in a 1:1 mixture of CH3CN/H2O (100μL) and purified by reverse-phase HPLC column as the final purification step.
  • 56
  • [ 3615-17-6 ]
  • [ 1448670-86-7 ]
  • [ 113-24-6 ]
  • [ 1448670-87-8 ]
YieldReaction ConditionsOperation in experiment
87% With Escherichia coli sialic acid aldolase; Neisseria meningitidis cytidine 5′-triphosphate-sialic acid synthetase; Pasteurella multocida α2–3-sialyltransferase 3; cytidine triphosphate; magnesium chloride In aq. buffer at 37℃; for 16h; Enzymatic reaction; 4.8 One-pot three-enzyme synthesis of ST-MUC1 glycopeptides APG(Siaα2-3Galβ1-3GalNAcα)STAPPA General procedure: T-MUC1 glycopeptide 7 (0.4mg, 0.3μmol, 1.0equiv), sodium pyruvate (5equiv), and CTP (2equiv) were dissolved in water in a 0.5mL centrifuge tube containing Tris-HCl buffer (100mM, pH 8.5) and MgCl2 (20mM). The resulting mixture was split equally to 4 tubes and ManNAc or its derivative (1.5equiv) was added to each tube. After the addition of EcNanA (25μg/mL), NmCSS (30μg/mL), and PmST3 (50μg/mL), millipore water was added to bring the volume to 80μL. The reaction and product purification were carried out similarly to those described above for the synthesis of STn-MUC1 glycopeptides.
  • 57
  • [ 113-24-6 ]
  • 2-acetamido-2,4-dideoxy-4-fluoro-D-mannopyranoside [ No CAS ]
  • [ 3150-24-1 ]
  • 4-nitrophenyl O-(7-fluoro-5-acetamido-3,5,7-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-O-β-D-galactopyranoside [ No CAS ]
  • 4-nitrophenyl O-(7-fluoro-5-acetamido-3,5,7-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→6)-O-β-D-galactopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 98% 2: 92% With cytidine 5′-triphosphate disodium salt; neisseria meningitides CMP-sialicacid synthetase; pasteurella multocida sialic acidaldolase; magnesium chloride In aq. buffer at 37℃; Inert atmosphere; Enzymatic reaction; General procedure for one-pot three-enzyme preparativescalesynthesis of a2-3- and a2-6-linked sialosides General procedure: GalpNP (1.0 equiv, 10 mM, 0.1 mmol), a sialic acid precursor(1.5 equiv, 15 mM, 0.15 mmol) chosen from 1a-8a, sodium pyruvate(10.0 equiv, 100 mM, 1 mmol), and CTP (2.0 equiv, 20 mM,0.2 mmol) were dissolved in water in a 50 mL centrifuge tube containingTris-HCl buffer (100 mM, pH 8.5) and MgCl2 (20 mM). Afteradding appropriate amounts of Pasteurella multocida sialic acidaldolase30 (PmNanA, 0.7-1.1 mg), Neisseria meningitides CMP-sialicacid synthetase31 (NmCSS, 1.0-1.3 mg), and a sialyltransferase(PmST16, 0.1-0.2 mg or Pd2,6ST7, 0.3-0.5 mg), water was addedto bring the volume of the reaction mixture to 10 mL. The reactionwas incubated at 37 C in an isotherm incubator with agitating at120 rpm for 3-16 h using PmST1 or 16-48 h using Pd2,6ST. Theproduct formation was monitored by TLC using EtOAc/MeOH/H2O/AcOH = 7:2:0.5:0.1 (by volume) as the developing solventand stained with p-anisaldehyde sugar stain solution. The reactionwas terminated by adding the same volume (10 mL) of ice-coldEtOH followed by incubation at 4 C for 30 min. The mixture wascentrifuged to remove precipitates. The supernatant was concentratedand passed through a Bio-gel P-2 gel filtration column withwater as the eluant to obtain the desired product. Silica gel columnpurification (EtOAc/MeOH/H2O = 7:2:0.6, by volume) was used forfurther purification.
  • 58
  • 4-deoxy-4-fluoro-D-mannopyranoside [ No CAS ]
  • [ 113-24-6 ]
  • [ 3150-24-1 ]
  • 4-nitrophenyl O-(3,7-dideoxy-7-fluoro-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-O-β-D-galactopyranoside [ No CAS ]
  • 4-nitrophenyl O-(3,9-dideoxy-7-fluoro-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→6)-O-β-D-galactopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 98% 2: 95% With cytidine 5′-triphosphate disodium salt; neisseria meningitides CMP-sialicacid synthetase; pasteurella multocida sialic acidaldolase; magnesium chloride In aq. buffer at 37℃; Inert atmosphere; Enzymatic reaction; General procedure for one-pot three-enzyme preparativescalesynthesis of a2-3- and a2-6-linked sialosides General procedure: GalpNP (1.0 equiv, 10 mM, 0.1 mmol), a sialic acid precursor(1.5 equiv, 15 mM, 0.15 mmol) chosen from 1a-8a, sodium pyruvate(10.0 equiv, 100 mM, 1 mmol), and CTP (2.0 equiv, 20 mM,0.2 mmol) were dissolved in water in a 50 mL centrifuge tube containingTris-HCl buffer (100 mM, pH 8.5) and MgCl2 (20 mM). Afteradding appropriate amounts of Pasteurella multocida sialic acidaldolase30 (PmNanA, 0.7-1.1 mg), Neisseria meningitides CMP-sialicacid synthetase31 (NmCSS, 1.0-1.3 mg), and a sialyltransferase(PmST16, 0.1-0.2 mg or Pd2,6ST7, 0.3-0.5 mg), water was addedto bring the volume of the reaction mixture to 10 mL. The reactionwas incubated at 37 C in an isotherm incubator with agitating at120 rpm for 3-16 h using PmST1 or 16-48 h using Pd2,6ST. Theproduct formation was monitored by TLC using EtOAc/MeOH/H2O/AcOH = 7:2:0.5:0.1 (by volume) as the developing solventand stained with p-anisaldehyde sugar stain solution. The reactionwas terminated by adding the same volume (10 mL) of ice-coldEtOH followed by incubation at 4 C for 30 min. The mixture wascentrifuged to remove precipitates. The supernatant was concentratedand passed through a Bio-gel P-2 gel filtration column withwater as the eluant to obtain the desired product. Silica gel columnpurification (EtOAc/MeOH/H2O = 7:2:0.6, by volume) was used forfurther purification.
  • 59
  • [ 113-24-6 ]
  • 2-acetylamino-2-deoxy-4-O-methyl-D-mannopyranose [ No CAS ]
  • [ 3150-24-1 ]
  • 4-nitrophenyl O-(5-acetamido-3,5-dideoxy-7-O-methyl-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-O-β-D-galactopyranoside [ No CAS ]
  • 4-nitrophenyl O-(5-acetamido-3,5-dideoxy-7-O-methyl-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→6)-O-β-D-galactopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 95% 2: 57% With cytidine 5′-triphosphate disodium salt; neisseria meningitides CMP-sialicacid synthetase; pasteurella multocida sialic acidaldolase; magnesium chloride In aq. buffer at 37℃; Inert atmosphere; Enzymatic reaction; General procedure for one-pot three-enzyme preparativescalesynthesis of a2-3- and a2-6-linked sialosides General procedure: GalpNP (1.0 equiv, 10 mM, 0.1 mmol), a sialic acid precursor(1.5 equiv, 15 mM, 0.15 mmol) chosen from 1a-8a, sodium pyruvate(10.0 equiv, 100 mM, 1 mmol), and CTP (2.0 equiv, 20 mM,0.2 mmol) were dissolved in water in a 50 mL centrifuge tube containingTris-HCl buffer (100 mM, pH 8.5) and MgCl2 (20 mM). Afteradding appropriate amounts of Pasteurella multocida sialic acidaldolase30 (PmNanA, 0.7-1.1 mg), Neisseria meningitides CMP-sialicacid synthetase31 (NmCSS, 1.0-1.3 mg), and a sialyltransferase(PmST16, 0.1-0.2 mg or Pd2,6ST7, 0.3-0.5 mg), water was addedto bring the volume of the reaction mixture to 10 mL. The reactionwas incubated at 37 C in an isotherm incubator with agitating at120 rpm for 3-16 h using PmST1 or 16-48 h using Pd2,6ST. Theproduct formation was monitored by TLC using EtOAc/MeOH/H2O/AcOH = 7:2:0.5:0.1 (by volume) as the developing solventand stained with p-anisaldehyde sugar stain solution. The reactionwas terminated by adding the same volume (10 mL) of ice-coldEtOH followed by incubation at 4 C for 30 min. The mixture wascentrifuged to remove precipitates. The supernatant was concentratedand passed through a Bio-gel P-2 gel filtration column withwater as the eluant to obtain the desired product. Silica gel columnpurification (EtOAc/MeOH/H2O = 7:2:0.6, by volume) was used forfurther purification.
  • 60
  • [ 113-24-6 ]
  • [ 637011-89-3 ]
  • [ 3150-24-1 ]
  • 4-nitrophenyl O-(5-acetamido-3,5,7-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-O-β-D-galactopyranoside [ No CAS ]
  • 4-nitrophenyl O-(5-acetamido-3,5,7-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→6)-O-β-D-galactopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 80% 2: 88% With cytidine 5′-triphosphate disodium salt; neisseria meningitides CMP-sialicacid synthetase; pasteurella multocida sialic acidaldolase; magnesium chloride In aq. buffer at 37℃; Inert atmosphere; Enzymatic reaction; General procedure for one-pot three-enzyme preparativescalesynthesis of a2-3- and a2-6-linked sialosides General procedure: GalpNP (1.0 equiv, 10 mM, 0.1 mmol), a sialic acid precursor(1.5 equiv, 15 mM, 0.15 mmol) chosen from 1a-8a, sodium pyruvate(10.0 equiv, 100 mM, 1 mmol), and CTP (2.0 equiv, 20 mM,0.2 mmol) were dissolved in water in a 50 mL centrifuge tube containingTris-HCl buffer (100 mM, pH 8.5) and MgCl2 (20 mM). Afteradding appropriate amounts of Pasteurella multocida sialic acidaldolase30 (PmNanA, 0.7-1.1 mg), Neisseria meningitides CMP-sialicacid synthetase31 (NmCSS, 1.0-1.3 mg), and a sialyltransferase(PmST16, 0.1-0.2 mg or Pd2,6ST7, 0.3-0.5 mg), water was addedto bring the volume of the reaction mixture to 10 mL. The reactionwas incubated at 37 C in an isotherm incubator with agitating at120 rpm for 3-16 h using PmST1 or 16-48 h using Pd2,6ST. Theproduct formation was monitored by TLC using EtOAc/MeOH/H2O/AcOH = 7:2:0.5:0.1 (by volume) as the developing solventand stained with p-anisaldehyde sugar stain solution. The reactionwas terminated by adding the same volume (10 mL) of ice-coldEtOH followed by incubation at 4 C for 30 min. The mixture wascentrifuged to remove precipitates. The supernatant was concentratedand passed through a Bio-gel P-2 gel filtration column withwater as the eluant to obtain the desired product. Silica gel columnpurification (EtOAc/MeOH/H2O = 7:2:0.6, by volume) was used forfurther purification.
  • 61
  • [ 113-24-6 ]
  • 2-acetamido-4-azido-2,4-dideoxy-D-mannopyranoside [ No CAS ]
  • [ 3150-24-1 ]
  • 4-nitrophenyl O-(7-azido-5-acetamido-3,5,7-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→6)-O-β-D-galactopyranoside [ No CAS ]
  • C23H30N5O15(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 80% 2: 98% With cytidine 5′-triphosphate disodium salt; neisseria meningitides CMP-sialicacid synthetase; pasteurella multocida sialic acidaldolase; magnesium chloride In aq. buffer at 37℃; Inert atmosphere; Enzymatic reaction; General procedure for one-pot three-enzyme preparativescalesynthesis of a2-3- and a2-6-linked sialosides General procedure: GalpNP (1.0 equiv, 10 mM, 0.1 mmol), a sialic acid precursor(1.5 equiv, 15 mM, 0.15 mmol) chosen from 1a-8a, sodium pyruvate(10.0 equiv, 100 mM, 1 mmol), and CTP (2.0 equiv, 20 mM,0.2 mmol) were dissolved in water in a 50 mL centrifuge tube containingTris-HCl buffer (100 mM, pH 8.5) and MgCl2 (20 mM). Afteradding appropriate amounts of Pasteurella multocida sialic acidaldolase30 (PmNanA, 0.7-1.1 mg), Neisseria meningitides CMP-sialicacid synthetase31 (NmCSS, 1.0-1.3 mg), and a sialyltransferase(PmST16, 0.1-0.2 mg or Pd2,6ST7, 0.3-0.5 mg), water was addedto bring the volume of the reaction mixture to 10 mL. The reactionwas incubated at 37 C in an isotherm incubator with agitating at120 rpm for 3-16 h using PmST1 or 16-48 h using Pd2,6ST. Theproduct formation was monitored by TLC using EtOAc/MeOH/H2O/AcOH = 7:2:0.5:0.1 (by volume) as the developing solventand stained with p-anisaldehyde sugar stain solution. The reactionwas terminated by adding the same volume (10 mL) of ice-coldEtOH followed by incubation at 4 C for 30 min. The mixture wascentrifuged to remove precipitates. The supernatant was concentratedand passed through a Bio-gel P-2 gel filtration column withwater as the eluant to obtain the desired product. Silica gel columnpurification (EtOAc/MeOH/H2O = 7:2:0.6, by volume) was used forfurther purification.
  • 62
  • [ 27552-11-0 ]
  • [ 113-24-6 ]
  • [ 3150-24-1 ]
  • 4-nitrophenyl O-(3-deoxy-7-O-methyl-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-O-β-D-galactopyranoside [ No CAS ]
  • 4-nitrophenyl O-(7-azido-5-acetamido-3,5,7-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→6)-O-β-D-galactopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 89% 2: 53% With cytidine 5′-triphosphate disodium salt; neisseria meningitides CMP-sialicacid synthetase; pasteurella multocida sialic acidaldolase; magnesium chloride In aq. buffer at 37℃; Inert atmosphere; Enzymatic reaction; General procedure for one-pot three-enzyme preparativescalesynthesis of a2-3- and a2-6-linked sialosides General procedure: GalpNP (1.0 equiv, 10 mM, 0.1 mmol), a sialic acid precursor(1.5 equiv, 15 mM, 0.15 mmol) chosen from 1a-8a, sodium pyruvate(10.0 equiv, 100 mM, 1 mmol), and CTP (2.0 equiv, 20 mM,0.2 mmol) were dissolved in water in a 50 mL centrifuge tube containingTris-HCl buffer (100 mM, pH 8.5) and MgCl2 (20 mM). Afteradding appropriate amounts of Pasteurella multocida sialic acidaldolase30 (PmNanA, 0.7-1.1 mg), Neisseria meningitides CMP-sialicacid synthetase31 (NmCSS, 1.0-1.3 mg), and a sialyltransferase(PmST16, 0.1-0.2 mg or Pd2,6ST7, 0.3-0.5 mg), water was addedto bring the volume of the reaction mixture to 10 mL. The reactionwas incubated at 37 C in an isotherm incubator with agitating at120 rpm for 3-16 h using PmST1 or 16-48 h using Pd2,6ST. Theproduct formation was monitored by TLC using EtOAc/MeOH/H2O/AcOH = 7:2:0.5:0.1 (by volume) as the developing solventand stained with p-anisaldehyde sugar stain solution. The reactionwas terminated by adding the same volume (10 mL) of ice-coldEtOH followed by incubation at 4 C for 30 min. The mixture wascentrifuged to remove precipitates. The supernatant was concentratedand passed through a Bio-gel P-2 gel filtration column withwater as the eluant to obtain the desired product. Silica gel columnpurification (EtOAc/MeOH/H2O = 7:2:0.6, by volume) was used forfurther purification.
  • 63
  • [ 24707-42-4 ]
  • [ 113-24-6 ]
  • [ 3150-24-1 ]
  • 4-nitrophenyl O-(3,7-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-O-β-D-galactopyranoside [ No CAS ]
  • 4-nitrophenyl O-(3,7-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→6)-O-β-D-galactopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 90% 2: 58% With cytidine 5′-triphosphate disodium salt; neisseria meningitides CMP-sialicacid synthetase; pasteurella multocida sialic acidaldolase; magnesium chloride In aq. buffer at 37℃; Inert atmosphere; Enzymatic reaction; General procedure for one-pot three-enzyme preparativescalesynthesis of a2-3- and a2-6-linked sialosides General procedure: GalpNP (1.0 equiv, 10 mM, 0.1 mmol), a sialic acid precursor(1.5 equiv, 15 mM, 0.15 mmol) chosen from 1a-8a, sodium pyruvate(10.0 equiv, 100 mM, 1 mmol), and CTP (2.0 equiv, 20 mM,0.2 mmol) were dissolved in water in a 50 mL centrifuge tube containingTris-HCl buffer (100 mM, pH 8.5) and MgCl2 (20 mM). Afteradding appropriate amounts of Pasteurella multocida sialic acidaldolase30 (PmNanA, 0.7-1.1 mg), Neisseria meningitides CMP-sialicacid synthetase31 (NmCSS, 1.0-1.3 mg), and a sialyltransferase(PmST16, 0.1-0.2 mg or Pd2,6ST7, 0.3-0.5 mg), water was addedto bring the volume of the reaction mixture to 10 mL. The reactionwas incubated at 37 C in an isotherm incubator with agitating at120 rpm for 3-16 h using PmST1 or 16-48 h using Pd2,6ST. Theproduct formation was monitored by TLC using EtOAc/MeOH/H2O/AcOH = 7:2:0.5:0.1 (by volume) as the developing solventand stained with p-anisaldehyde sugar stain solution. The reactionwas terminated by adding the same volume (10 mL) of ice-coldEtOH followed by incubation at 4 C for 30 min. The mixture wascentrifuged to remove precipitates. The supernatant was concentratedand passed through a Bio-gel P-2 gel filtration column withwater as the eluant to obtain the desired product. Silica gel columnpurification (EtOAc/MeOH/H2O = 7:2:0.6, by volume) was used forfurther purification.
  • 64
  • [ 113-24-6 ]
  • [ 3150-24-1 ]
  • 4-azido-4-deoxy-D-mannopyranoside [ No CAS ]
  • 4-nitrophenyl O-(7-azido-3,7-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-O-β-D-galactopyranoside [ No CAS ]
  • 4-nitrophenyl O-(7-azido-3,7-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→6)-O-β-D-galactopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 98% 2: 89% With cytidine 5′-triphosphate disodium salt; neisseria meningitides CMP-sialicacid synthetase; pasteurella multocida sialic acidaldolase; magnesium chloride In aq. buffer at 37℃; Inert atmosphere; Enzymatic reaction; General procedure for one-pot three-enzyme preparativescalesynthesis of a2-3- and a2-6-linked sialosides General procedure: GalpNP (1.0 equiv, 10 mM, 0.1 mmol), a sialic acid precursor(1.5 equiv, 15 mM, 0.15 mmol) chosen from 1a-8a, sodium pyruvate(10.0 equiv, 100 mM, 1 mmol), and CTP (2.0 equiv, 20 mM,0.2 mmol) were dissolved in water in a 50 mL centrifuge tube containingTris-HCl buffer (100 mM, pH 8.5) and MgCl2 (20 mM). Afteradding appropriate amounts of Pasteurella multocida sialic acidaldolase30 (PmNanA, 0.7-1.1 mg), Neisseria meningitides CMP-sialicacid synthetase31 (NmCSS, 1.0-1.3 mg), and a sialyltransferase(PmST16, 0.1-0.2 mg or Pd2,6ST7, 0.3-0.5 mg), water was addedto bring the volume of the reaction mixture to 10 mL. The reactionwas incubated at 37 C in an isotherm incubator with agitating at120 rpm for 3-16 h using PmST1 or 16-48 h using Pd2,6ST. Theproduct formation was monitored by TLC using EtOAc/MeOH/H2O/AcOH = 7:2:0.5:0.1 (by volume) as the developing solventand stained with p-anisaldehyde sugar stain solution. The reactionwas terminated by adding the same volume (10 mL) of ice-coldEtOH followed by incubation at 4 C for 30 min. The mixture wascentrifuged to remove precipitates. The supernatant was concentratedand passed through a Bio-gel P-2 gel filtration column withwater as the eluant to obtain the desired product. Silica gel columnpurification (EtOAc/MeOH/H2O = 7:2:0.6, by volume) was used forfurther purification.
  • 65
  • [ 867-56-1 ]
  • [ 113-24-6 ]
  • 66
  • [ 2613-22-1 ]
  • [ 113-24-6 ]
  • 3-chloro-2-fluoro-4-vinyl phenol [ No CAS ]
  • 67
  • [ 1504-74-1 ]
  • [ 113-24-6 ]
  • sodium 2-methoxycinnamylidenepyruvate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In methanol; water; at 5 - 25℃; for 3h;Cooling with ice; General procedure: The <strong>[1504-74-1]2-methoxycinnamaldehyde</strong>, (CH3O-C6H4-(CH)2-CHO) 96%pure predominantly trans, was obtained from Aldrich and sodiumpyruvate (H3C-CO-COONa) 99% pure from Sigma.Sodium 2-methoxycinnamylidenepyruvate (Na-2-MeO-CP)and its corresponding acid were both synthesized following theprocedure described in the literature [10], with some modifica-tions which include an aqueous solution of sodium pyruvate (8.71 gper 10 mL) added under continuous stirring to 20 mL of methano-lic solution of <strong>[1504-74-1]2-methoxycinnamaldehyde</strong> (13.23 g). Sixty-threemilliliters of an aqueous sodium hydroxide solution 5% (m/v) wasslowly added while the reacting system was stirred and cooledin an ice bath. The addition rate of alkali was regulated so thatthe temperature remained between 5 and 9C. The formation of apale yellow precipitate was observed during the addition of sodiumhydroxide solution.The system was left to stand for about 3 h at temperaturebetween 23 and 25C. The pale yellow precipitate (impure sodium2-methoxycinnamylidenepyruvate) was filtered and washed with100 mL portions of methanol to remove most of the unreacted alde-hyde and secondary products. The crude product was dissolved inwater (200 mL) and concentrated hydrochloric acid (12 mol L-1)was added to the solutions under continuous stirring until totalprecipitation of 2-methoxycinnamylidenepyruvic acid (4.8 g).
  • 68
  • [ 453-17-8 ]
  • [ 113-24-6 ]
  • [ 162284-35-7 ]
  • [ 162284-34-6 ]
  • [ 60299-43-6 ]
  • 69
  • 2,6-diacetamido-2,6-dideoxy-D-mannopyranose [ No CAS ]
  • [ 113-24-6 ]
  • [ 3150-24-1 ]
  • 4-nitrophenyl O-(5,9-diacetamido-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-O-β-D-galactopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With CTP(3Na+); Neisseria meningitidis CMP-sialic acid synthetase; pasteurella multocida sialic acidaldolase; Pasteurella multocidasialyltransferase 1 M144D mutant; magnesium chloride In aq. buffer at 37℃; Enzymatic reaction; 2.15 1.2 One-pot three-enzyme synthesis of α2-3/6-linked sialosides General procedure: An acceptor (30-50mg, 10mM) and ManNAc6NAc (1.2-1.5 equiv.) were incubated at 37°C in Tris-HCl buffer (100mM) (pH 8.5 for synthesizing α2-3-sialosides or α2-6-sialosides using Psp2,6STA366G, pH 7.5 for synthesizing α2-6-sialosides using Pd2,6ST) containing sodium pyruvate (6.0-7.5 equiv.), CTP (1.5 equiv.), MgCl2 (20mM), an appropriate amount of PmAldolase (1.5mg), NmCSS (2.5mg), and Pd2,6ST (2.5mg), Psp2,6ST A366G mutant (2.5mg), or PmST1 M144D mutant (2.5mg). The reaction was monitored by thin-layer chromatography (TLC) using a developing solvent consisting of EtOAc:MeOH:H2O=5:2:1 (by volume) and the TLC plates were stained with a p-anisaldehyde sugar stain. After 1-24h, the reaction was quenched by adding the same volume of pre-chilled ethanol and the reaction mixture was centrifuged to remove precipitates. The supernatant was concentrated and passed through a BioGel P-2 gel filtration column eluting with water followed by a C18 column (H2O:CH3CN=1:0-4:1) to obtain the target products.
80% With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida sialic acid aldolase; pasteurella multocida 2-3-sialyltransferase 1 M144D mutant; cytidine triphosphate; magnesium chloride In aq. buffer at 37℃; Enzymatic reaction; 7 General procedure: An acceptor (30-50 mg, 10 mM) and ManNAc6NAc (1.2-1.5 equiv.) were incubated at 37 °C in Tris-HCl buffer ( 100 mM) (pH 8.5 for synthesizing oc2-3 -sialosides or a2-6-sialosides using Psp2,6STA366G, pH 7.5 for synthesizing cc2-6-sialosides using Pd2,6ST) containing sodium pyruvate (6.0-7.5 equiv.), CTP (1.5 equiv.), MgC . (20 raMj, an appropriate amount of PmAldolase (1.5 mg), NmCSS (2.5 mg), and Pd2,6ST (2.5 mg), Psp2,6ST A366G mutant (2.5 mg), or PmSTl M144D mutant (2.5 mg). The reaction was monitored by thin-layer chromatography (TLC) using a developing solvent consisting of EtOAciMeOHiffcO = 5:2: 1 (by volume) and the TLC plates were stained with ap- anisaldehyde sugar stain. After 1-24 h, the reaction was quenched by adding the same volume of pre-chilled ethanol and the reaction mixture was centrifuged to remove precipitates. The supernatant was concentrated and passed through a BioGel P-2 gel filtration column eluting with water followed by a C18 column 1:0 - 4: 1) to obtain the target products.As shown in Table 2, using PmSTl M144D as the sialyltransferase, oc2-3-linked sialosides (2.1-2.7) were obtained in 61-86% yields. These are comparable to the synthesis of 2-3-sialyllactoside, Neu5Ac9NAca2-3Gaipi-4GlcpProN3, which was obtained in 84% yield. Two 2-6-sialyitransferases were used for synthesizing o 2-6-linked sialosides (2.8- 2.16). Psp2,6ST A366G mutant with an increased expression level and improved activities in sialylating Tn antigens was used for synthesizing Neu5Ac9NAca2-6Ga1NAcaProN3 (2.16) with 71% yield. For other 2-6-linked Neu5Ac9NAc-containing sialosides (2.8-2.15) synthesized, both Pd2,6ST and Psp2,6ST A366G could provide similar yields in small scale reactions. Pd2,6ST was used for the synthesis of Neu5Ac9NAca2-6GaipProN3 (2.9) and Neu5 Ac9NAc 2-6Gal l-3GalNAcaProN3 (2.12) with excellent 92% and 98% yields, respectively. Due to the higher expression level of Psp2,6ST A366G, it was used for the synthesis of the rest of the a2-6-linked sialoside targets (2.8, 2.10-2.11, 2.13-2.15). Good to excellent yields (64-96%) were obtained. 4-Nitrophenyl 0-(5,9-diacetamido-3,5,9-trideoxy-D-glycero-a-D-galacto-2- nomdopyranosylonie acid)-(2-→3)-0-P-D-galactopyranoside (Neu5Ac9NAcoc2- 3( βρΝΡ, 2.1). Yield 80%; 87 mg, White foam. NMR (400 MHz, D2O) δ 8.32-8.15 (rn, 2H), 7.32-7.1 7 (m, 2H), 5.29 (d, J = 7.8 Hz, IH), 4,25 (dd, J = 3.2 and 9.8 Hz, 1H), 4.06 (d, J - 3.2 Hz, IH), 3.98-3.84 (m, 4H), 3.81-3.64 (m, 4H), 3.61-3.46 (m, 2H), 3.29 (dd, J = 7.6 and 14.2 Hz, 1H), 2.80 (dd, ./ 4.6 and 12,4 Hz, 1H), 2,04 (s, 3H), 1 ,95 (s, 3H), 1.84 (t, ,/ 12.1 Hz, I II);13C NMR ( 100 MHz, D2O) δ 174,95, 174.32, 173.75, 161.70, 142.47,126.07(2C), 1 16.41 (2C), 99.94, 99.70, 75 ,50, 75.45, 72.76, 70.00, 69.60, 68.77, 68.29, 67,29, 60.67, 51.67, 42.10, 39.67, 22.03, 21.75; HRMS (ESI) Anal. Calcd for C25H34N3O16 [M-H]": 632.1945, Found: 632.1957.
  • 70
  • 2,6-diacetamido-2,6-dideoxy-D-mannopyranose [ No CAS ]
  • [ 113-24-6 ]
  • [ 3150-24-1 ]
  • 4-nitrophenyl O-(5,9-diacetamido-3,5,9-trideoxy-D-glycero-α-D-gaIacto-2-nonulopyranosylonic acid)-(2→6)-O-β-D-galactopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With CTP(3Na+); Neisseria meningitidis CMP-sialic acid synthetase; pasteurella multocida sialic acidaldolase; Photobacterium sp. α2-6 sialyltransferase A366G mutants; magnesium chloride In aq. buffer at 37℃; Enzymatic reaction; 2.15 1.2 One-pot three-enzyme synthesis of α2-3/6-linked sialosides General procedure: An acceptor (30-50mg, 10mM) and ManNAc6NAc (1.2-1.5 equiv.) were incubated at 37°C in Tris-HCl buffer (100mM) (pH 8.5 for synthesizing α2-3-sialosides or α2-6-sialosides using Psp2,6STA366G, pH 7.5 for synthesizing α2-6-sialosides using Pd2,6ST) containing sodium pyruvate (6.0-7.5 equiv.), CTP (1.5 equiv.), MgCl2 (20mM), an appropriate amount of PmAldolase (1.5mg), NmCSS (2.5mg), and Pd2,6ST (2.5mg), Psp2,6ST A366G mutant (2.5mg), or PmST1 M144D mutant (2.5mg). The reaction was monitored by thin-layer chromatography (TLC) using a developing solvent consisting of EtOAc:MeOH:H2O=5:2:1 (by volume) and the TLC plates were stained with a p-anisaldehyde sugar stain. After 1-24h, the reaction was quenched by adding the same volume of pre-chilled ethanol and the reaction mixture was centrifuged to remove precipitates. The supernatant was concentrated and passed through a BioGel P-2 gel filtration column eluting with water followed by a C18 column (H2O:CH3CN=1:0-4:1) to obtain the target products.
64% With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida sialic acid aldolase; photobacterium sp. α2-6-sialyltransferase A366G mutant; cytidine triphosphate; magnesium chloride In aq. buffer at 37℃; Enzymatic reaction; 7 General procedure: An acceptor (30-50 mg, 10 mM) and ManNAc6NAc (1.2-1.5 equiv.) were incubated at 37 °C in Tris-HCl buffer ( 100 mM) (pH 8.5 for synthesizing oc2-3 -sialosides or a2-6-sialosides using Psp2,6STA366G, pH 7.5 for synthesizing cc2-6-sialosides using Pd2,6ST) containing sodium pyruvate (6.0-7.5 equiv.), CTP (1.5 equiv.), MgC . (20 raMj, an appropriate amount of PmAldolase (1.5 mg), NmCSS (2.5 mg), and Pd2,6ST (2.5 mg), Psp2,6ST A366G mutant (2.5 mg), or PmSTl M144D mutant (2.5 mg). The reaction was monitored by thin-layer chromatography (TLC) using a developing solvent consisting of EtOAciMeOHiffcO = 5:2: 1 (by volume) and the TLC plates were stained with ap- anisaldehyde sugar stain. After 1-24 h, the reaction was quenched by adding the same volume of pre-chilled ethanol and the reaction mixture was centrifuged to remove precipitates. The supernatant was concentrated and passed through a BioGel P-2 gel filtration column eluting with water followed by a C18 column 1:0 - 4: 1) to obtain the target products.As shown in Table 2, using PmSTl M144D as the sialyltransferase, oc2-3-linked sialosides (2.1-2.7) were obtained in 61-86% yields. These are comparable to the synthesis of 2-3-sialyllactoside, Neu5Ac9NAca2-3Gaipi-4GlcpProN3, which was obtained in 84% yield. Two 2-6-sialyitransferases were used for synthesizing o 2-6-linked sialosides (2.8- 2.16). Psp2,6ST A366G mutant with an increased expression level and improved activities in sialylating Tn antigens was used for synthesizing Neu5Ac9NAca2-6Ga1NAcaProN3 (2.16) with 71% yield. For other 2-6-linked Neu5Ac9NAc-containing sialosides (2.8-2.15) synthesized, both Pd2,6ST and Psp2,6ST A366G could provide similar yields in small scale reactions. Pd2,6ST was used for the synthesis of Neu5Ac9NAca2-6GaipProN3 (2.9) and Neu5 Ac9NAc 2-6Gal l-3GalNAcaProN3 (2.12) with excellent 92% and 98% yields, respectively. Due to the higher expression level of Psp2,6ST A366G, it was used for the synthesis of the rest of the a2-6-linked sialoside targets (2.8, 2.10-2.11, 2.13-2.15). Good to excellent yields (64-96%) were obtained. 4-Nitrophenyl 0-(5,9-diacetamido-3,5,9-trideoxy-D-glycero-(X-D-gaIacto-2- nonulopyranosylesiie acid)~(2-→6)~0- -D-galactopyranosde (Neu5Ac9NAcoc2- 6( βρΝΡ, 2.8), Yield 64%: 69 mg, White foam, NMR (400 MHz, D2O) δ 8,26-8.15 (m, 2H), 7.26-7.12 (m, 2H), 5.09 (d, J = 7.6 Hz, 1H), 3.95 (dd, J = 4,0 and 7.6 Hz, 2H), 3.91- 3.56 (m, 8H), 3.47 (dd, J = 2.8 and 14.2 Hz, 11 1). 3.36 (dd, J = 1.6 and 8.8 Hz, 1H), 3.14 (dd, j = 8.0 and 14.2 Hz, 1H), 2.67 (dd, J = 4.4 and 12.4 Hz, 1H), 1.94 (s, 3H), 1.86 (s, 3H), 1.67- 1 .49 (m, 1H);:'C N.MR ( ()() MHz, D2O) δ 174.94, 174.30, 173.48, 161.84, 142,51, 126.12(2C), 116.39(2C), 100.42, 99,88, 74.04, 72.47, 72.33, 70,2.5, 69.96, 69.69, 68.36,68.15, 63 ,02, 51.80, 42.15, 40.14, 21,98, 21.72; HRMS (ESI) Anal. Calcd for C25H34N3O16 I M i i j": 632.1945, Found: 632.1955.
  • 71
  • 2,4-diazido-2,4,6-trideoxy-D-mannose [ No CAS ]
  • [ 113-24-6 ]
  • [ 3150-24-1 ]
  • C21H27N7O13 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida sialic acid aldolase; pasteurella multocida 2-3-sialyltransferase 1 M144D mutant; cytidine triphosphate; magnesium chloride In water at 30℃; for 48h; Enzymatic reaction; 12 Leg5,7diN3a2-3GaiPpNP (3-13) GalfipNP ( 15 mg, 0.050 mmol), 2,4-di~azido~6~ deoxy-mannose (16 mg, 0.075 mmol), sodium, pyruvate (38 mg, 0.35 mmol ).. CTP (39 mg, 0,075 mmol) were dissolved in water in a 15 ml, centrifuge tube containing Tris-HCl buffer (100 mM, pH 8.5) and MgCh (20 mM). After adding sialic acid aldolase (0.5 mg), NmCSS (0.5 mg), and a sialyltransferase PmSTl M144D (1.5 mg) water was added to bring the final volume to 5 niL. The reaction mixture was incubated at 30 °C for 48 h. Tire reaction progress was monitored using TLC (EtQAeiMeQHiH O = 6: 1 : 1, by volume) and mass spectrometry. Tire reaction mixture was diluted with the same volume of ethanol and incubated at 4 °C for 30 min. The mixture was then centrifuged and concentrated, wrhich was purified by automated flash chromatograph using CI 8 column (CftCN in H2O gradient was used as running solvents) to produce 3-13 (22 mg, 73%). NMR (800 MHz, D2O) δ 8.28 (d, J = 9.2 Hz, II I). 7.25 (d, J = 9,2 Hz, 2H), 5.28 (d, / = 7.8 Hz, i l l). 4.18-4.13 (m, 2H), 4.05-3.99 (m, 1H), 3 ,89 (q, ,/ 8.4, 6.9 Hz, 2H), 3.79-3.72 (m, 3H), 3.70 (d, J ----- 10.3 Hz, lH), 3.61-3.55 (m, 1H), 3.42 (d, ./ 8.7 Hz, 1H), 2.75 dd. ./ 12.7, 4.6 Hz, 1H), 1.91 i t. ./ 12.3 Hz, 1H), 1.37 (d, ,/ = 6.4 Hz, 3H).13C NMR (200 MHz, D2O) δ 172.87, 161 , 19, 142.04, 125.60, 1 15.93, 100.08, 99,08, 75.07, 74.91, 7.1.76, 68,94, 68.20, 67.12, 66,05, 64.80, 62.86, 60.14, 38.46, 18.33. HRMS (ESI) m/∑ calculated for C21H27N7O13 (M-H) 585, 1594, found 585 , 1583 ,
  • 72
  • 2,4-diazido-2,4,6-trideoxy-D-mannose [ No CAS ]
  • [ 113-24-6 ]
  • [ 3150-24-1 ]
  • C21H27N7O13 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida sialic acid aldolase; photobacterium species α2-6-sialyltransferase; cytidine triphosphate; magnesium chloride In water at 30℃; for 48h; Enzymatic reaction; 12 Leg5,7diN32-6GiiP/?NP (3-14) GaiftoNP (15 mg, 0.050 mmol), 2,4-di-azido-6- deoxy-mannose (16 mg, 0.075 mmol), sodium pyruvate (38 mg, 0.35 mmol), CTP (39 mg, 0.075 mmol) were dissolved in water in a 15 mL centrifuge tube containing Tris-HCl buffer (100 mM, pH 8.5) and MgCh (20 mM). After adding sialic acid aldolase (0.5 mg), NmCSS (0.5 mg), and Psp2,6ST (1.5 mg) water was added to bring the final volume to 5 mL. The reaction mixture was incubated at 30 °C for 48 h. The reaction progress was monitored using TLC (EtOAc:MeOH:tbO:=:6: 1: 1, by volume) and mass spectrometry. The reaction mixture was diluted with the same volume of ethanol and incubated at 4 °C for 30 min. The mixture was then centrifuged and concentrated, which was purified by automated flashchromatograph using C18 column (CftCN in H2O gradient was used as mnning solvents) to produce 3-14 (21 mg, 70%). NMR (800 MHz, D2O) δ 8.29 (d, J= 8,8 Hz, 2H), 7.26 (d, ./ - 9.6 Hz, 2H), 5.18 id../ 7.2 Hz, 1H), 4.09-4.04 (m, 1H), 4.01 (d. ./ 3.3 Hz, 1H), 3.97 (dd, J= 7,6, 4.5 Hz, 1H), 3,88 (dd, ./= 10.5, 7.8 Hz, 1H), 3.86-3 ,83 (m, 1H), 3.78 (dd, J = 10.0, 3.4 Hz, 1H), 3.75-3.69 (m, 2H), 3 ,67 (dd, J= 10.6, 4.4 Hz, 1H), 3.48 (dd, J= 8.6, 2.2 Hz, 1H), 3.43 (t, J ------ 9.8 Hz, 1H), 2.74-2.71 (m, 1H), 1.71 (t, J ------- 12.3 Hz, 1H), 1.34 (d, J=6,4 Hz, 3H).13C NMR (200 MHz, D2O) δ 172.62, 161.33, 142,01, 125.58, 1 16.04, 100.08, 99.26, 73.56, 71.85, 71 ,37, 69.78, 68.82, 67.89, 66,25, 65.35, 63.13, 62,77, 39.50, 18.29. HRMS (ESI) m/z calculated for C21H27N7O13 (M-H) 585.1594, found 585.1589
  • 73
  • [ 113-24-6 ]
  • [ 112641-20-0 ]
  • C11H6F4O3 [ No CAS ]
  • 74
  • [ 3615-17-6 ]
  • 3-azidopropyl 3-O-sulfo-β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)[-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside [ No CAS ]
  • [ 113-24-6 ]
  • 3-azidopropyl 3-O-sulfo-β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)[5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl-(2→3)-β-D–galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida α2−3-sialyltransferase 1 M144D mutant; pasteurella multocida aldolase; Neisseria meningitides β1−4-galactosyltransferase; cytidine triphosphate In aq. buffer at 37℃; Enzymatic reaction;
  • 75
  • [ 3615-17-6 ]
  • 3-azidopropyl 3-O-sulfo-β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)[β-D-galactopyranosyl-(1→4)[α-L-fucopyranosyl-(1→3)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside [ No CAS ]
  • [ 113-24-6 ]
  • 3-azidopropyl 3-O-sulfo-β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)[5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl-(2→3)-β-D-galactopyranosyl-(1→4)[α-L-fucopyranosyl-(1→3)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida α2−3-sialyltransferase 1 M144D mutant; pasteurella multocida aldolase; Neisseria meningitides β1−4-galactosyltransferase; cytidine triphosphate In aq. buffer at 37℃; Enzymatic reaction;
  • 76
  • [ 3615-17-6 ]
  • 3-azidopropyl β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)[3-O-sulfo-β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside [ No CAS ]
  • [ 113-24-6 ]
  • 3-azidopropyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl-(2→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)[3-O-sulfo-β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida α2−3-sialyltransferase 1 M144D mutant; pasteurella multocida aldolase; Neisseria meningitides β1−4-galactosyltransferase; cytidine triphosphate In aq. buffer at 37℃; Enzymatic reaction;
  • 77
  • [ 3615-17-6 ]
  • 3-azidopropyl β-D-galactopyranosyl-(1→4)[α-L-fucopyranosyl-(1→3)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)[3-O-sulfo-β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside [ No CAS ]
  • [ 113-24-6 ]
  • 3-azidopropyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl-(2→3)-β-D-galactopyranosyl-(1→4)[α-L-fucopyranosyl-(1→3)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)[3-O-sulfo-β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida α2−3-sialyltransferase 1 M144D mutant; pasteurella multocida aldolase; Neisseria meningitides β1−4-galactosyltransferase; cytidine triphosphate In aq. buffer at 37℃; Enzymatic reaction;
  • 78
  • [ 3615-17-6 ]
  • 3-azidopropyl β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)[β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside [ No CAS ]
  • [ 113-24-6 ]
  • 3-azidopropyl β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2){5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl-(2→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)}-α-D-mannopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida α2−3-sialyltransferase 1 M144D mutant; pasteurella multocida aldolase; Neisseria meningitides β1−4-galactosyltransferase; cytidine triphosphate In aq. buffer at 37℃; Enzymatic reaction;
  • 79
  • [ 3615-17-6 ]
  • 3-azidopropyl β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)[β-D-galactopyranosyl-(1→4)-[α-L-fucopyranosyl-(1→3)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside [ No CAS ]
  • [ 113-24-6 ]
  • 3-azidopropyl β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2){5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl-(2→3)-β-D-galactopyranosyl-(1→4)[α-L-fucopyranosyl-(1→3)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)}-α-D-mannopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida α2−3-sialyltransferase 1 M144D mutant; pasteurella multocida aldolase; Neisseria meningitides β1−4-galactosyltransferase; cytidine triphosphate In aq. buffer at 37℃; Enzymatic reaction;
  • 80
  • [ 3615-17-6 ]
  • 3-azidopropyl β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside [ No CAS ]
  • [ 113-24-6 ]
  • 3-azidopropyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl-(2→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)[β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida α2−3-sialyltransferase 1 M144D mutant; pasteurella multocida aldolase; Neisseria meningitides β1−4-galactosyltransferase; cytidine triphosphate In aq. buffer at 37℃; Enzymatic reaction;
  • 81
  • [ 3615-17-6 ]
  • 3-azidopropyl β-D-galactopyranosyl-(1→4)[α-L-fucopyranosyl-(1→3)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)[β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside [ No CAS ]
  • [ 113-24-6 ]
  • 3-azidopropyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl-(2→3)-β-D-galactopyranosyl-(1→4)[α-L-fucopyranosyl-(1→3)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)[β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida α2−3-sialyltransferase 1 M144D mutant; pasteurella multocida aldolase; Neisseria meningitides β1−4-galactosyltransferase; cytidine triphosphate In aq. buffer at 37℃; Enzymatic reaction;
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 113-24-6 ]

Aliphatic Chain Hydrocarbons

Chemical Structure| 127-17-3

[ 127-17-3 ]

2-Oxopropanoic acid

Similarity: 0.95

Chemical Structure| 4151-33-1

[ 4151-33-1 ]

Potassiumpyruvate

Similarity: 0.90

Chemical Structure| 52009-14-0

[ 52009-14-0 ]

Calcium 2-oxopropanoate

Similarity: 0.90

Chemical Structure| 2013-26-5

[ 2013-26-5 ]

Sodium 2-oxobutanoate

Similarity: 0.83

Chemical Structure| 473-90-5

[ 473-90-5 ]

2-Oxomalonic acid

Similarity: 0.82

Ketones

Chemical Structure| 127-17-3

[ 127-17-3 ]

2-Oxopropanoic acid

Similarity: 0.95

Chemical Structure| 4151-33-1

[ 4151-33-1 ]

Potassiumpyruvate

Similarity: 0.90

Chemical Structure| 52009-14-0

[ 52009-14-0 ]

Calcium 2-oxopropanoate

Similarity: 0.90

Chemical Structure| 2013-26-5

[ 2013-26-5 ]

Sodium 2-oxobutanoate

Similarity: 0.83

Chemical Structure| 473-90-5

[ 473-90-5 ]

2-Oxomalonic acid

Similarity: 0.82

Carboxylic Acid Salts

Chemical Structure| 52009-14-0

[ 52009-14-0 ]

Calcium 2-oxopropanoate

Similarity: 0.90

Chemical Structure| 2013-26-5

[ 2013-26-5 ]

Sodium 2-oxobutanoate

Similarity: 0.83