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  • 3616-42-0, D-氨基葡萄糖-6-磷酸, D-Glucosamine 6-phosphate, GLCN-6-p, CAS:3616-42-0
  • 3616-42-0, D-氨基葡萄糖-6-磷酸, D-Glucosamine 6-phosphate, GLCN-6-p, CAS:3616-42-0
3616-42-0, D-氨基葡萄糖-6-磷酸, D-Glucosamine 6-phosphate, GLCN-6-p, CAS:3616-42-03616-42-0, D-氨基葡萄糖-6-磷酸, D-Glucosamine 6-phosphate, GLCN-6-p, CAS:3616-42-0

3616-42-0, D-氨基葡萄糖-6-磷酸, D-Glucosamine 6-phosphate, GLCN-6-p, CAS:3616-42-0

D-氨基葡萄糖-6-磷酸,
D-Glucosamine 6-phosphate,
GLCN-6-p,
CAS:3616-42-0
MDL No.:MFCD00067382
M.F.:C6H14NO8P
M.W.:259.15

D-氨基葡萄糖 6-磷酸, D-Glucosamine 6-phosphate

D-Glucosamine 6-phosphate, the natural form of glucosamine, is a monosaccharide produced during hexosamine biosynthesis pathway by the enzyme glucosamine-6-phosphate deaminase from the two substrates fructose 6-phosphate and glutamine.

Glucosamine 6-phosphate, also known as GLCN-6-p or glucose-6-phosphoric acid, belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. Glucosamine 6-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, glucosamine 6-phosphate is primarily located in the cytoplasm and lysosome. Glucosamine 6-phosphate exists in all eukaryotes, ranging from yeast to humans. Glucosamine 6-phosphate participates in a number of enzymatic reactions. In particular, Glucosamine 6-phosphate and L-glutamic acid can be biosynthesized from fructose 6-phosphate and L-glutamine; which is mediated by the enzyme glutamine--fructose-6-phosphate aminotransferase. Furthermore, Acetyl-CoA and glucosamine 6-phosphate can be converted into N-acetyl-D-glucosamine 6-phosphate; which is mediated by the enzyme glucosamine 6-phosphate N-acetyltransferase. Furthermore, Glucosamine 6-phosphate and acetic acid can be biosynthesized from N-acetyl-D-glucosamine 6-phosphate; which is mediated by the enzyme putative N-acetylglucosamine-6-phosphate deacetylase. Finally, Glucosamine 6-phosphate can be converted into N-acetyl-D-glucosamine 6-phosphate; which is catalyzed by the enzyme glucosamine 6-phosphate N-acetyltransferase. In humans, glucosamine 6-phosphate is involved in the amino sugar metabolism pathway, the glutamate metabolism pathway, and the homocarnosinosis pathway. Glucosamine 6-phosphate is also involved in several metabolic disorders, some of which include the salla disease/infantile sialic Acid storage disease pathway, the g(m2)-gangliosidosis: variant b, tay-sachs disease pathway, the hyperinsulinism-hyperammonemia syndrome pathway, and the tay-sachs disease pathway.

Alpha-D-glucosamine 6-phosphate is a 2-amino-2-deoxy-D-glucopyranose 6-phosphate that has an alpha-configuration at the anomeric position. It has a role as a human metabolite and a Saccharomyces cerevisiae metabolite. It derives from an alpha-D-glucosamine. It is a conjugate acid of an alpha-D-glucosamine 6-phosphate(1-).

CAS Number3616-42-0
Product NameD-glucosamine-6-phosphate
IUPAC Name[(2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxohexyl] dihydrogen phosphate
Molecular FormulaC6H14NO8P
Molecular Weight259.15 g/mol
InChIInChI=1S/C6H14NO8P/c7-3(1-8)5(10)6(11)4(9)2-15-16(12,13)14/h1,3-6,9-11H,2,7H2,(H2,12,13,14)/t3-,4+,5+,6+/m0/s1
InChI KeyAEJSSXDYDSUOOZ-SLPGGIOYSA-N
SMILESC(C(C(C(C(C=O)N)O)O)O)OP(=O)(O)O
Synonyms2-Amino-2-deoxy-D-glucose 6-(Dihydrogen Phosphate) Hydrate; Glucosamine 6-Phosphate Hydrate; 2-Amino-2-deoxy-D-glucose 6-Phosphate Hydrate; 2-Amino-2-deoxyglucose 6-Phosphate Hydrate; 2-Amino-D-glucose-6-phosphate Hydrate; D-Glucosamine 6-Phosphate
Canonical SMILESC(C(C(C(C(C=O)N)O)O)O)OP(=O)(O)O
Isomeric SMILESC([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)N)O)O)OP(=O)(O)O


D-Glucosamine 6-phosphate is a non-essential amino acid that belongs to the group of nucleotide sugar phosphates. It is a metabolite of the sugar D-glucose and it plays an important role in the energy metabolism of bacteria, plants, and animals. It has been shown to have anti-cancer effects on prostate cancer cells. D-Glucosamine 6-phosphate inhibits methyltransferase activity by binding to the enzyme's active site. This inhibition prevents DNA synthesis, leading to cell death. The structural analysis has been done using NMR spectroscopy on d-arabinose as a model substrate.

CAS:3616-42-0

MDL No.:MFCD00067382

M.F.:C6H14NO8P

M.W.:259.15


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