D-Glucosamine 6-phosphate (gam6p)

Human Metabolome Database (HMDB): Glucosamine 6-phosphate (CAS: 3616-42-0) is normally produced in endothelial cells via de novo glucosamine synthesis by the enzyme fructose-6-phosphate amidotransferase and the modulation of this pathway by hyperglycemia and glutamine. Glutamine-fructose-6-phosphate amidotransferase (GFAT) catalyzes the first committed step in the pathway for biosynthesis of hexosamines in mammals.It is a member of the N-terminal nucleophile class of amidotransferases, GFAT transfers the amino group from the L-glutamine amide to D-fructose 6-phosphate, producing glutamic acid and glucosamine 6-phosphate. As glucosamine inhibits endothelial nitric oxide synthesis it has important implications for impaired endothelium-dependent relaxation and vascular dysfunction in diabetes mellitus (PMID:11270676, 11842094).

Charged formula:

C6H13NO8P

Charge:

-1

InChIKey:

XHMJOUIAFHJHBW-IVMDWMLBSA-M

SMILES:

[H]OC1([H])O[C@]([H])(C([H])([H])OP(=O)([O-])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])N([H])[H]

External links: hmdb.cakegg.jpebi.ac.ukpubchem.ncbi.nlm.nih.gov

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