 | |
| Names | |
|---|---|
| IUPAC name Uridine 5′-(2-acetamido-2-deoxy-α-D-glucopyranosyl dihydrogen diphosphate) | |
| Systematic IUPAC name O1-[(2R,3R,4R,5S,6R)-3-Acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]O3-{[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxyoxolan-2-yl]methyl} dihydrogen diphosphate | |
| Other names UDP-N-acetylglucosamine; UDP-GlcNAc | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider | |
| DrugBank | |
| KEGG | |
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| Properties | |
| C17H27N3O17P2 | |
| Molar mass | 607.355 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Uridine diphosphateN-acetylglucosamine orUDP-GlcNAc is anucleotide sugar and acoenzyme inmetabolism. It is used byglycosyltransferases to transferN-acetylglucosamine residues to substrates. UDP-GlcNAc is used for makingglycosaminoglycans,proteoglycans, andglycolipids.[1]D-Glucosamine is made naturally in the form of glucosamine-6-phosphate, and is the biochemical precursor of allnitrogen-containing sugars.[2] To be specific, glucosamine-6-phosphate is synthesized fromfructose 6-phosphate andglutamine[3] as the first step of thehexosamine biosynthesis pathway.[4] The end-product of this pathway is UDP-GlcNAc. Some enzymes involved in the biosynthesis of UDP-GlcNAc vary betweenprokaryotic andeukaryotic organisms, serving as potential drug targets for antibiotic development.[5]
UDP-GlcNAc is extensively involved inintracellular signaling as a substrate forO-linkedN-acetylglucosamine transferases (OGTs) to install theO-GlcNAcpost-translational modification in a wide range of species. It is also involved innuclear pore formation and nuclear signalling. OGTs and OG-ases play an important role in the structure of thecytoskeleton. In mammals, there is enrichment of OGT transcripts in thepancreasbeta-cells, and UDP-GlcNAc is thought to be part of the glucose sensing mechanism. There is also evidence that it plays a part ininsulin sensitivity in other cells. In plants, it is involved in the control ofgibberellin production.[6] In eukaryoticstem cells, the presence of UDP-GlcNAc is essential for maintainingpluripotency, which is sustained through O-GlcNAcylation.[7]
Clostridium novyi type A alpha-toxin is anO-linkedN-actetylglucosamine transferase acting onRho proteins and causing the collapse of the cytoskeleton.
There is a possible relationship between the inhibition of oxidative phosphorylation and reduced UDP-GlcNAc levels.[7]
UDP-GlcNAc biosynthesis is not regulated by the same enzymes in prokaryotic and eukaryotic organisms. The lack of the bifunctionalGlmUacetyltransferase and pyrophosphorylase in eukaryotes makes it a possible target for blocking UDP-GlcNAc synthesis (an essential precursor for peptidoglycan synthesis) in bacteria without affecting host cells.[5]
