| Uridine diphosphate N-acetylglucosamine | |
|---|---|
|
[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate |
|
|
Other names
UDP-N-acetylglucosamine; UDP-GlcNAc |
|
| Identifiers | |
| CAS number | 7277-98-7 |
| PubChem | 445675 |
| Jmol-3D images | Image 1 |
|
|
| Properties | |
| Molecular formula | C17H27N3O17P2 |
| Molar mass | 607.35 g mol−1 |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
|
| Infobox references | |
Uridine diphosphate N-acetylglucosamine or UDP-GlcNAc is a nucleotide sugar and a coenzyme in metabolism. It is used by glycosyltransferases to transfer N-acetylglucosamine residues to substrates. D-Glucosamine is made naturally in the form of glucosamine-6-phosphate, and is the biochemical precursor of all nitrogen-containing sugars.[1] To be specific, glucosamine-6-phosphate is synthesized from fructose 6-phosphate and glutamine[2] as the first step of the hexosamine biosynthesis pathway.[3] The end-product of this pathway is UDP-GlcNAc, which is then used for making glycosaminoglycans, proteoglycans, and glycolipids.[4]
UDP-GlcNAc is extensively involved in intracellular signaling as a substrate for O-linked N-actetylglucosamine transferases (OGTs) in a wide range of species. It is also involved in nuclear pore formation and nuclear signalling. OGTs and OG-ases play an important role in the structure of the cytoskeleton. In mammals, there is enrichment of OGT transcripts in the pancreas beta-cells, and UDP-GlcNAc is thought to be part of the glucose sensing mechanism. There is also evidence that it plays a part in insulin sensitivity in other cells. In plants, it is involved in the control of gibberellin production.[5]
Clostridium novyi type A alpha-toxin is an O-linked N-actetylglucosamine transferase acting on Rho proteins and causing the collapse of the cytoskeleton.
|
||||||||