N-[(2S,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

• ChemBase ID: 133596
• Molecular Formular: C8H15NO6
• Molecular Mass: 221.2078
• Monoisotopic Mass: 221.08993721
• SMILES: CC(=O)N[C@H]1[C@H]([C@@H]([C@H](O[C@@H]1O)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H](O)[C@H]([C@H]([C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5+,6-,7-,8+/m1/s1
• InChIKey: OVRNDRQMDRJTHS-UOLFYFMNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-acetyl-α-D-mannosamine
• Synonyms: N-Acetyl-D-mannosamine; N-乙酰-D-甘露糖胺

Database IDs

• CAS Number: 7772-94-3
• PubChem SID: 24891208; 162227873
• PubChem CID: 644170

CALCULATED PROPERTIES

• Acid pKa: 11.60413
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.2205749
• LogD (pH = 7.4): -3.2206008
• Log P: -3.2205744
• Molar Refractivity: 47.0247 cm^3
• Polarizability: 19.398714 Å^3
• Polar Surface Area: 119.25 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (TLC)

DETAILS

Sigma Aldrich - A8176

Biochem/physiol Actions
N-Acetyl-D-mannosamine (ManNAc) is an essential precursor of N-acetylneuraminic acid (NeuAc), the specific monomer of polysialic acid. Transport studies in the E. coli K1 strain have been performed to probe the effect of ManNAc on capsular polysialic acid production.
包装
10 mg in autosmp vl
Application
N-Acetyl-D-mannosamine (ManNAc) is used as a substrate to identify, differentiate and characterize enzymes such as N-acetyl-glucosamine epimerase(s) and aldolase(s). N-Acetyl-D-mannosamine is used for the synthesis of of N-acetylneuraminic acid.
Protocols & Applications
Sialic Acid Synthesis and Signaling Overview