CHEBI:183051 - tetraacetyl-N-azidoacetyl-D-mannosamine

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ChEBI Name tetraacetyl-N-azidoacetyl-D-mannosamine
ChEBI ID CHEBI:183051
ChEBI ASCII Name tetraacetyl-N-azidoacetyl-D-mannosamine
Definition A monosaccharide derivative that is D-mannosamine in pyranose form with an azidocarbonyl group substituted on nitrogen and all hydroxy groups acetylated. It can be used to introduce an azido group in living cells which can be metabolized to N-azido acetylneuramic acid and eventually incorporated into the glycoproteins and glycolipids on the cell surface, while exhibiting very low toxicity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C15H20N4O10
Net Charge 0
Average Mass 416.343
Monoisotopic Mass 416.11794
InChI InChI=1S/C15H20N4O10/c1-6(20)25-5-10-12(26-7(2)21)13(27-8(3)22)11(17-15(24)18-19-16)14(29-10)28-9(4)23/h10-14H,5H2,1-4H3,(H,17,24)/t10-,11+,12-,13-,14?/m1/s1
InChIKey MRRKYEUMMAEYHG-DYPLGBCKSA-N
SMILES CC(=O)OC[C@H]1OC(OC(C)=O)[C@@H](NC(=O)N=[N+]=[N-])[C@@H](OC(C)=O)[C@@H]1OC(C)=O
Roles Classification
Biological Role(s): immunogen
An antigen capable, on its own, of inducing an immune response.
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ChEBI Ontology
Outgoing tetraacetyl-N-azidoacetyl-D-mannosamine (CHEBI:183051) has functional parent D-mannosamine (CHEBI:62324)
tetraacetyl-N-azidoacetyl-D-mannosamine (CHEBI:183051) has role immunogen (CHEBI:60816)
tetraacetyl-N-azidoacetyl-D-mannosamine (CHEBI:183051) is a acetate ester (CHEBI:47622)
tetraacetyl-N-azidoacetyl-D-mannosamine (CHEBI:183051) is a azide (CHEBI:22680)
tetraacetyl-N-azidoacetyl-D-mannosamine (CHEBI:183051) is a monosaccharide derivative (CHEBI:63367)
IUPAC Name
1,3,4,6-tetra-O-acetyl-2-[(azidocarbonyl)amino]-2-deoxy-D-mannopyranose
Synonyms Sources
2-[(azidocarbonyl)amino]-2-deoxy-D-mannopyranose 1,3,4,6-tetraacetate ChEBI
AC4ManNAz ChEBI
Citation Waiting for Citations Type Source
34158858 PubMed citation Europe PMC
Last Modified
22 October 2021