N-Acetylmannosamine - Moligand™,10mM in DMSO , CAS No.7772-94-3

CAS: 7772-94-3 Cat. No.: N425917 Molecular Weight: 221.21 EC Number: 616-491-5

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

7772-94-3|N-acetylmannosamine|N-((2R,3S,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide|N-Acetyl-beta-D-mannosamine|beta-ManNAc|N-[(2R,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide|N-acetyl-beta-mannosam

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

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.

Specifications

Synonyms

7772-94-3 | N-acetylmannosamine | N-((2R, 3S, 4R, 5S, 6R)-2, 4, 5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide | N-Acetyl-beta-D-mannosamine | beta-ManNAc | N-[(2R, 3S, 4R, 5S, 6R)-2, 4, 5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide | N-acetyl-beta-mannosam

Specifications & Purity

Moligand™, 10mM in DMSO

Biochemical and Physiological Mechanisms

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

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Names and Identifiers

• Canonical Smiles: CC(=O)NC1C(C(C(OC1O)CO)O)O
• IUPAC Name: N-[(2R,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• InChIKey: OVRNDRQMDRJTHS-OZRXBMAMSA-N
• 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
• Isomeric SMILES: CC(=O)N[C@H]1[C@H]([C@@H]([C@H](O[C@H]1O)CO)O)O
• Alternate CAS: 3615-17-6
• Molecular Weight: 221.21
• Reaxy-Rn: 1913591
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1913591&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Aminosaccharides
          • Level6 Amino sugars
            • Level7 Acylaminosugars

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Aminosaccharides - Amino sugars
• Direct Parent: Acylaminosugars
• Alternative Parents: N-acyl-alpha-hexosamines Hexoses Oxanes Acetamides Secondary carboxylic acid amides Secondary alcohols Hemiacetals Polyols Oxacyclic compounds Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Acylaminosugar - N-acyl-alpha-hexosamine - Hexose monosaccharide - Monosaccharide - Oxane - Acetamide - Carboxamide group - Hemiacetal - Secondary carboxylic acid amide - Secondary alcohol - Carboxylic acid derivative - Oxacycle - Organoheterocyclic compound - Polyol - Alcohol - Hydrocarbon derivative - Organic oxide - Organic nitrogen compound - Organopnictogen compound - Organonitrogen compound - Primary alcohol - Carbonyl group - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
• External Descriptors: N-acetyl-D-mannosamine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: Hygroscopic
• Molecular Weight: 221.210 g/mol
• XLogP3: -1.700
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 221.09 Da
• Monoisotopic Mass: 221.09 Da
• Topological Polar Surface Area: 119.000 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 235.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yue Sun, Shi-Qi Cheng, Junkai Ma, Fei Zhu, Wei Hong, Haibing Li.  (2020)  Biomimetic nanochannels platform for detecting N-acetylglucosamine analogues.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2020.128705]

2. Guimeng Xiao, Xiaonan Zhao, Shaoyun Shi, Jianxing Lu, Guiling Li, Fengying Gong, Xinming Feng, Juanjuan Liu, Dongdong Meng.  (2025)  Thermostable Whole-Cell Biocatalysts Enable Sustainable and Practical Synthesis of N-Acetylneuraminic Acid.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:41456346] [10.1021/acs.jafc.5c10911]