CHEBI:40356 - N-acetyl-α-D-galactosamine

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ChEBI Name N-acetyl-α-D-galactosamine
ChEBI ID CHEBI:40356
ChEBI ASCII Name N-acetyl-alpha-D-galactosamine
Definition An N-acetyl-D-galactosamine having α-configuration at the anomeric centre.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB5764857, eMolecules:30487763, ZINC000002562219
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Formula C8H15NO6
Net Charge 0
Average Mass 221.20780
Monoisotopic Mass 221.08994
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-CBQIKETKSA-N
SMILES CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@H](O)[C@@H]1O
Roles Classification
Biological Role(s): epitope
The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
(via N-acetyl-D-galactosamine )
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via N-acetyl-D-galactosamine )
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via N-acetyl-D-galactosamine )
(via N-acetylgalactosamine )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing N-acetyl-α-D-galactosamine (CHEBI:40356) has functional parent α-D-galactosamine (CHEBI:148869)
N-acetyl-α-D-galactosamine (CHEBI:40356) has role epitope (CHEBI:53000)
N-acetyl-α-D-galactosamine (CHEBI:40356) is a N-acetyl-D-galactosamine (CHEBI:28037)
Incoming α-D-GalpNAc-(1→3)-α-D-Galp (CHEBI:146643) has functional parent N-acetyl-α-D-galactosamine (CHEBI:40356)
α-D-GalpNAc-(1→3)-D-GlcpNAc (CHEBI:148388) has functional parent N-acetyl-α-D-galactosamine (CHEBI:40356)
α-D-GalpNAc-(1→6)-D-Galp (CHEBI:148285) has functional parent N-acetyl-α-D-galactosamine (CHEBI:40356)
α-D-GalpNAc-(1→6)-D-GalpNAc (CHEBI:148702) has functional parent N-acetyl-α-D-galactosamine (CHEBI:40356)
α-D-Glcp-(1→3)-α-D-GalpNAc (CHEBI:148178) has functional parent N-acetyl-α-D-galactosamine (CHEBI:40356)
β-D-Galp-(1→6)-α-D-GalpNAc (CHEBI:150906) has functional parent N-acetyl-α-D-galactosamine (CHEBI:40356)
β-D-GalpNAc-(1→6)-α-D-GalpNAc (CHEBI:152542) has functional parent N-acetyl-α-D-galactosamine (CHEBI:40356)
β-D-Glcp-(1→3)-α-D-GalpNAc (CHEBI:146727) has functional parent N-acetyl-α-D-galactosamine (CHEBI:40356)
2-acetamido-2-deoxy-α-D-Galp-(1→3)-2-acetamido-2-deoxy-D-Gal-OH (CHEBI:147876) has functional parent N-acetyl-α-D-galactosamine (CHEBI:40356)
N-acetyl-α-neuraminyl-(2→6)-N-acetyl-α-D-galactosamine (CHEBI:61818) has functional parent N-acetyl-α-D-galactosamine (CHEBI:40356)
N-acetyl-α-D-galactosaminyl group (CHEBI:88142) is substituent group from N-acetyl-α-D-galactosamine (CHEBI:40356)
IUPAC Name
2-acetamido-2-deoxy-α-D-galactopyranose
Synonyms Sources
2-(acetylamino)-2-deoxy-alpha-D-galactopyranose ChemIDplus
α-GalNAc ChEBI
α-GalpNAc ChEBI
GalNAc-α ChEBI
N-acetyl-α-D-galactosamine UniProt
Tn ChEBI
Tn antigen saccharide ChEBI
TN antigen saccharide ChEBI
Tn antigen saccharide component ChEBI
TN antigen saccharide component ChEBI
Tn saccharide ChEBI
TN saccharide ChEBI
Tn saccharide component ChEBI
TN saccharide component ChEBI
WURCS=2.0/1,1,0/[a2112h-1a_1-5_2*NCC/3=O]/1/ GlyTouCan
Manual Xrefs Databases
CPD-3604 MetaCyc
EP0788504 Patent
G57321FI GlyGen
G57321FI GlyTouCan
US5527891 Patent
View more database links
Registry Numbers Types Sources
14215-68-0 CAS Registry Number ChemIDplus
1429040 Reaxys Registry Number Reaxys
Citations
Dobrochaeva KL, Khasbiullina NR, Shilova NV, Obukhova PS, Knirel YA, Nokel AY, Bovin NV (2019)
Human antibodies eluted from ligand-free Sepharose capable of binding bacterial polysaccharides and sulfated glycans.
Molecular immunology 106, 63-68 [PubMed:30583222]
[show Abstract]
von Gunten S, Smith DF, Cummings RD, Riedel S, Miescher S, Schaub A, Hamilton RG, Bochner BS (2009)
Intravenous immunoglobulin contains a broad repertoire of anticarbohydrate antibodies that is not restricted to the IgG2 subclass.
The Journal of allergy and clinical immunology 123, 1268-76.e15 [PubMed:19443021]
[show Abstract]
Obukhova P, Rieben R, Bovin N (2007)
Normal human serum contains high levels of anti-Gal alpha 1-4GlcNAc antibodies.
Xenotransplantation 14, 627-635 [PubMed:17991151]
[show Abstract]
Coxon B (2005)
Deuterium isotope effects in carbohydrates revisited. Cryoprobe studies of the anomerization and NH to ND deuterium isotope induced 13C NMR chemical shifts of acetamidodeoxy and aminodeoxy sugars.
Carbohydrate research 340, 1714-1721 [PubMed:15936003]
[show Abstract]
Kjeldsen T, Hakomori S, Springer GF, Desai P, Harris T, Clausen H (1989)
Coexpression of sialosyl-Tn (NeuAc alpha 2----6GalNAc alpha 1----O-Ser/Thr) and Tn (GalNAc alpha 1----O-Ser/Thr) blood group antigens on Tn erythrocytes.
Vox sanguinis 57, 81-87 [PubMed:2800471]
[show Abstract]
Lipkind GM, Shashkov AS, Knirel YA, Vinogradov EV, Kochetkov NK (1988)
A computer-assisted structural analysis of regular polysaccharides on the basis of 13C-n.m.r. data.
Carbohydrate research 175, 59-75 [PubMed:3378242]
[show Abstract]
Last Modified
17 November 2021