N-Acetyl-D-mannosamine

N-Acetyl-D-mannosamine

N-Acetyl-D-mannosamine (ManNAc) (CAS No. 7772-94-3) is an N-acetylated derivative of D-mannosamine, classified as a hexosamine sugar with molecular formula C8H15NO6 and molecular weight 221.21 g/mol. It serves as a crucial biochemical precursor in the biosynthesis of sialic acids, particularly N-acetylneuraminic acid (Neu5Ac), which are important components of glycoproteins and glycolipids in mammals.pubchem.ncbi.nlm.nih+2

Chemical Identity and Structure

• IUPAC Name: N-[(2R,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamidehmdb
• Synonyms: ManNAc, 2-Acetamido-2-deoxy-D-mannose, N-Acetylmannosamine monohydrateicepharma+1
• Molecular Formula: C8H15NO6pubchem.ncbi.nlm.nih+1
• Molecular Weight: 221.21 g/mol (anhydrous); 239.22 g/mol (monohydrate)icepharma

Physical and Chemical Properties

• Appearance: White to almost white powder or crystalstcichemicals
• Melting Point: Approximately 118-125°Chmdb+1
• Solubility: Soluble in water; typically available with >98% purity (HPLC)tcichemicals
• Optical Rotation: Specific optical rotation data is consistent with D-configuration sugarshmdb

Biological Role and Applications

• ManNAc is the first committed precursor for biosynthesis of sialic acids (Neu5Ac), essential in cell surface glycosylation and signaling processes.hmdb
• It participates in the metabolic pathways involving UDP-GlcNAc 2-epimerase and ManNAc kinase enzymes encoded by the GNE gene involved in sialic acid biosynthesis.hmdb
• Has therapeutic potential in treatment of GNE myopathy and other glycosylation-related genetic diseases.icepharma+1
• Enhances sialylation in mammalian cell culture systems to improve yield and effectiveness of glycoprotein-based therapeutics.icepharma

Storage and Handling

• Store in a cool, dry, and dark place preferably below 15°C; stable under recommended conditions.tcichemicals

Regulatory and Identification Numbers

N-Acetyl-D-mannosamine is an essential biochemical building block in glycoscience with significant applications in biotechnology and therapeutic development.pubchem.ncbi.nlm.nih+1