C6H13NO9P

C6H13NO9P is the molecular formula for glucosamine-6-phosphate (GlcN-6-P), an amino sugar phosphate that serves as a key intermediate in carbohydrate metabolism. The molecule combines a hexose sugar backbone bearing an amino group at C-2 with a phosphate ester at the terminal carbon (C-6).

Biological role: In humans and other organisms, GlcN-6-P is formed in the hexosamine biosynthetic pathway, primarily by the enzyme glutamine-fructose-6-phosphate amidotransferase (GFAT) from fructose-6-phosphate and glutamine. It acts as a precursor for UDP-N-acetylglucosamine (UDP-GlcNAc), which is used in protein glycosylation and the synthesis of glycosaminoglycans, as well as in the biosynthesis of chitin and peptidoglycan in certain microbes.

Physical properties: Molecular weight is approximately 274.17 g/mol. The compound is highly polar and water-soluble; at physiological pH it bears charges from both the amino group and the phosphate group, often existing as a zwitterion or other ionized forms in solution.

Occurrence and metabolism: GlcN-6-P occurs in both prokaryotes and eukaryotes. In bacteria it is a branch point leading to cell wall biosynthesis; in animals it contributes to pathways that generate essential glycoproteins and extracellular matrix components through downstream products such as UDP-GlcNAc.

See also: hexosamine biosynthetic pathway; UDP-N-acetylglucosamine; glucosamine.