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| 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 | 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 Temp | Store at -80°C |
| Shipped In |
Ice chest + Ice pads This product requires cold chain shipping. Ground and other economy services are not available. |
| Product Description |
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. |
Taxonomy Tree
| 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 |
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| IUPAC Name | N-[(2R,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide |
|---|---|
| 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-OZRXBMAMSA-N |
| Smiles | CC(=O)NC1C(C(C(OC1O)CO)O)O |
| Isomeric SMILES | CC(=O)N[C@H]1[C@H]([C@@H]([C@H](O[C@H]1O)CO)O)O |
| 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= |
| 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 |
| 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, 323 (128705). |