N-Acetylneuraminic acid
Conditions | Yield |
---|---|
Stage #1: 5-(1-acetylamino-2,3,4,5-tetrahydroxy-pentyl)-2-tert-butyl-isoxazolidine-3-carboxylic acid ethyl ester With sodium methylate In methanol at 20℃; Stage #2: With water for 24h; |
Conditions | Yield |
---|---|
With potassium phosphate buffer; magnesium chloride In water; xylene at 28℃; for 32h; pH=8.0; |
Conditions | Yield |
---|---|
With potassium phosphate buffer; D-glucose; magnesium chloride In water; xylene at 28℃; for 32h; pH=8.0; |
N-acetyl-D-mannosamine
sodium lactate
N-Acetylneuraminic acid
Conditions | Yield |
---|---|
With tris hydrochloride; Pseudomonas stutzeri SDM cells (lactate oxidase) In water; toluene at 30℃; for 20h; pH=7.0; Microbiological reaction; | 5.93 g |
N-Acetylneuraminic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydrogen carbonate / methanol / 1 h 2.1: dioxane / 336 h / 30 °C 3.1: NaOMe / methanol / 20 °C 3.2: water / 24 h View Scheme |
N-Acetylneuraminic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: dioxane / 336 h / 30 °C 2.1: NaOMe / methanol / 20 °C 2.2: water / 24 h View Scheme |
N-Acetylneuraminic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: trifluoroacetic acid / ethanol / 16 h 2.1: sodium hydrogen carbonate / methanol / 1 h 3.1: dioxane / 336 h / 30 °C 4.1: NaOMe / methanol / 20 °C 4.2: water / 24 h View Scheme |
N-Acetylneuraminic acid
Conditions | Yield |
---|---|
With recombinant oxidoreductase from Ruminococcus gnavus ATCC 29149; NADH In aq. phosphate buffer at 37℃; pH=7.5; Catalytic behavior; Solvent; Time; Reagent/catalyst; Enzymatic reaction; |
Conditions | Yield |
---|---|
With Amberlite IR 120 H(1+) form at 20℃; for 15h; | 100% |
With Dowex 50 x 8 (H(1+) form) for 2h; Ambient temperature; | |
With Amberlite IR-120 (H+) ion-exchange resin |
N-Acetylneuraminic acid
Conditions | Yield |
---|---|
With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida α2,3-sialyltransferase 3; cytidine triphosphate; magnesium chloride In aq. buffer at 37℃; pH=8.5; Green chemistry; Enzymatic reaction; | 96% |
N-Acetylneuraminic acid
N-acetylneuraminic acid methyl ester
Conditions | Yield |
---|---|
In methanol | 95% |
methanol
N-Acetylneuraminic acid
N-acetylneuraminic acid methyl ester
Conditions | Yield |
---|---|
With Amberlite IR-120 resin H(1+) form | 92% |
N-Acetylneuraminic acid
3-azidopropyl (β-D-galactopyranosyl)-(1→4)-O-2-deoxy-2-acetamido-β-D-glucopyranoside
Conditions | Yield |
---|---|
With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida α2,3-sialyltransferase 3; cytidine triphosphate; magnesium chloride In aq. buffer at 37℃; pH=8.5; Green chemistry; Enzymatic reaction; | 91% |
N-Acetylneuraminic acid
Conditions | Yield |
---|---|
With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida α2,3-sialyltransferase 3; cytidine triphosphate; magnesium chloride In aq. buffer at 37℃; pH=8.5; Green chemistry; Enzymatic reaction; | 91% |
N-Acetylneuraminic acid
Conditions | Yield |
---|---|
With phospho(enol)pyruvic acid mono potassium salt; cytidine triphosphate; ATP In aq. buffer at 37℃; pH=7.5; Enzymatic reaction; | 90% |
N-Acetylneuraminic acid
Conditions | Yield |
---|---|
With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida α2,3-sialyltransferase 3; cytidine triphosphate; magnesium chloride In aq. buffer at 37℃; pH=8.5; Green chemistry; Enzymatic reaction; | 87% |
N-Acetylneuraminic acid
Conditions | Yield |
---|---|
With phospho(enol)pyruvic acid mono potassium salt; cytidine triphosphate; ATP In aq. buffer at 37℃; pH=7.5; Enzymatic reaction; | 80% |
N-Acetylneuraminic acid
3-azidopropyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside
3-azidopropyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-β-D-galactopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-galactopyranoside
Conditions | Yield |
---|---|
With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida α2,3-sialyltransferase1 mutant; cytidine triphosphate; magnesium chloride In aq. buffer at 37℃; pH=8.5; Green chemistry; Enzymatic reaction; | 76% |
methanol
N-Acetylneuraminic acid
N-Acetyl-β-D-neuraminylsaeure-methyl-methylglycosid
Conditions | Yield |
---|---|
With ion exchange resin Dowex 50x8 H+ for 72h; Reflux; | 71% |
N-Acetylneuraminic acid
3-azidopropyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranoside
3-azidopropyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl-(2→3)-β-D-galactopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranoside
Conditions | Yield |
---|---|
With Neisseria meningitidis CMP-sialic acid synthetase; Pasteurella multocida α2,3-sialyltransferase1 mutant; cytidine triphosphate; magnesium chloride In aq. buffer at 37℃; pH=8.5; Green chemistry; Enzymatic reaction; | 63% |
N-Acetylneuraminic acid
5-aminopentyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate-(2→6)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-α-D-mannopyranosyl-(1→3)-[di(α-D-mannopyranosyl)-(1→3),(1→6)-α-D-mannopyranosyl]-(1→6)-β-D-mannopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranoside
Conditions | Yield |
---|---|
With phospho(enol)pyruvic acid mono potassium salt; cytidine triphosphate; ATP In aq. buffer at 37℃; for 48h; pH=7.5; Enzymatic reaction; | 60% |
N-Acetylneuraminic acid
5-aminopentyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate-(2→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-α-D-mannopyranosyl-(1→3)-[di(α-D-mannopyranosyl)-(1→3),(1→6)-α-D-mannopyranosyl]-(1→6)-β-D-mannopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranoside
Conditions | Yield |
---|---|
With phospho(enol)pyruvic acid mono potassium salt; cytidine triphosphate; ATP In aq. buffer at 37℃; for 192h; pH=7.5; Enzymatic reaction; | 56% |
N-Acetylneuraminic acid
Conditions | Yield |
---|---|
With phospho(enol)pyruvic acid mono potassium salt; cytidine triphosphate; ATP In aq. buffer at 37℃; for 96h; pH=7.5; Enzymatic reaction; | 52% |
Conditions | Yield |
---|---|
With pyrophosphatase; α-2,6-sialyltransferase; cytidine triphosphate; CMP-sialic acid synthetases; magnesium chloride; manganese(ll) chloride In aq. buffer Enzymatic reaction; | 50% |
N-Acetylneuraminic acid
5-amino-O2-methyl-β-D-glycero-D-galacto-3,5-dideoxy-[2]nonulopyranosonic acid
Conditions | Yield |
---|---|
With hydrogenchloride; methanol at 105℃; |
N-Acetylneuraminic acid
ethanethiol
5-Acetamino-3,5-didesoxy-D-glycero-D-galakto-2-keto-nononsaeure-γ-lacton-diethylmercaptal
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
With Dowex 50 x 8 (H(1+) form) for 3h; Ambient temperature; |
N-Acetylneuraminic acid
Conditions | Yield |
---|---|
With hydrogen fluoride |
Lactose
N-acetyl-D-galactosamine
N-Acetylneuraminic acid
A
O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic-acid)-(2-3)-O-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-β-D-galactopyranose
Conditions | Yield |
---|---|
With Triton-X-100; Na-cacodylate buffer; potassium chloride; phospho(enol)pyruvic acid mono potassium salt; cytidine monophosphate; cytidine triphosphate; magnesium chloride; manganese(ll) chloride In water at 37℃; for 82h; myokinase from porcine muscle, pyruvate kinase, inorganical phosphatase, CMP-Neu5Ac-synthase from calf brain, β-galactosidase from bovine testes, α-2,3-sialyltransferase from rat liver; pH 7.5; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
N-acetyl-D-galactosamine
N-Acetylneuraminic acid
A
O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic-acid)-(2-3)-O-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-β-D-galactopyranose
B
O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic-acid)-(2-3)-O-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-α-D-galactopyranose
Conditions | Yield |
---|---|
With Triton-X-100; Na-cacodylate buffer; potassium chloride; phospho(enol)pyruvic acid mono potassium salt; cytidine monophosphate; cytidine triphosphate; magnesium chloride; manganese(ll) chloride In water at 37℃; for 82h; myokinase from porcine muscle, pyruvate kinase, inorganical phosphatase, CMP-Neu5Ac-synthase from calf brain, β-galactosidase from bovine testes, α-2,3-sialyltransferase from rat liver; pH 7.5; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
N-Acetylneuraminic acid
N-Acetylneuraminic acid
N-acetyl neuraminic acid
Conditions | Yield |
---|---|
With formic acid; water |
N-Acetylneuraminic acid
4-(acetylamino)-2,4-dideoxy-D-glycero-D-galacto-octonic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide In phosphate buffer at 37℃; pH=6 - 8; Kinetics; Further Variations:; pH-values; Solvents; Temperatures; |
IUPAC Name: (2S,4S,5R,6R)-5-Acetamido-2,4-dihydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
Synonyms of N-Acetylneuraminic Acid (CAS NO.131-48-6): Aceneuramic acid ; Acide aceneuramique ; Acidium aceneuramicum ; Acido aceneuramico ; (-)-5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acid ; Neuraminic acid, N-acetyl-
CAS NO: 131-48-6
Molecular Formula: C11H19NO9
Molecular Weight: 309.27
Molecular Structure:
EINECS: 205-023-1
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 22 Å2
Index of Refraction: 1.752
Molar Refractivity: 52.97 cm3
Molar Volume: 129.7 cm3
Surface Tension: 63.5 dyne/cm
Density: 1.727 g/cm3
Flash Point: 193 °C
Enthalpy of Vaporization: 64.57 kJ/mol
Boiling Point: 395.6 °C at 760 mmHg
Vapour Pressure: 1.82E-06 mmHg at 25°C
Melting point: 184-186 ºC
Alpha: -32 º (c=2,water)
Water solubility: 50 g/L (20 ºC)
Storage temp: −20°C
Sensitive: Air Sensitive
Stability: Stable. Incompatible with strong oxidizing agents.
Appearance: Crystalline
Product Categories of N-Acetylneuraminic Acid (CAS NO.131-48-6): Bioproducts;Sugar derivatives;Miscellaneous Natural Products;Zanamavir;13C & 2H Sugars;Sialic Acids;Biochemistry;Sugar Acids;Sugars;Carbohydrates & Derivatives;Miscellaneous Compounds
Along with involvement in preventing infections, N-Acetylneuraminic Acid (CAS NO.131-48-6) acts as a receptor for influenza viruses, allowing attachment to mucous cells via hemaglutinin.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-36-26
S22: Do not breathe dust.
S24/25: Avoid contact with skin and eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
WGK Germany: 3
F: 3-10-23
Hazard Note: Irritant
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media: In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage: Store N-Acetylneuraminic Acid (CAS NO.131-48-6) in a cool, dry place. Keep container closed when not in use. Deep freeze (below -20°C). Keep refrigerated. (Store below 4°C/39°F.)
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