| 词条 | Uridine diphosphate N-acetylglucosamine |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 428729548 | Name = Uridine diphosphate N-acetylglucosamine | ImageFile = UDP-N-acetylglucosamine.png | ImageSize = 200px | IUPACName = [(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 | OtherNames = UDP-N-acetylglucosamine; UDP-GlcNAc |Section1={{Chembox Identifiers | IUPHAR_ligand = 1779 | CASNo_Ref = {{cascite|changed|??}} | CASNo = 91183-98-1 | PubChem = 445675 | SMILES = CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OP(=O)(O)OP(=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)CO)O)O }} |Section2={{Chembox Properties | C=17 | H=27 | N=3 | O=17 | P=2 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}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-acetylglucosamine 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. References1. ^{{cite journal | doi = 10.1074/jbc.R100053200 | last1 = Roseman | first1 = S | title = Reflections on glycobiology | journal = The Journal of Biological Chemistry | volume = 276 | issue = 45 | pages = 41527–42 | year = 2001 | pmid = 11553646 }} {{Nucleotide sugars}}{{Purinergics}}{{portal bar|Metabolism}}2. ^{{cite journal | author1 = Sudhamoy Ghosh | last2 = Blumenthal | first2 = HJ | last3 = Davidson | first3 = E | last4 = Roseman | first4 = S | title = Glucosamine Metabolism | url = http://www.jbc.org/cgi/reprint/235/5/1265 | journal = Journal of Biological Chemistry | volume = 235 | issue = 5 | pages = 1265–73 | date = 1960-05-01 | pmid = 13827775 }} 3. ^International Union of Biochemistry and Molecular Biology 4. ^{{cite journal |vauthors=Milewski S, Gabriel I, Olchowy J |title=Enzymes of UDP-GlcNAc biosynthesis in yeast |journal=Yeast |volume=23 |issue=1 |pages=1–14 |year=2006 |pmid=16408321 |doi=10.1002/yea.1337}} 5. ^{{cite journal | last1 = Hanover | first1 = J. A. | year = 2001 | title = Glycan-dependent signaling: O-linked N-acetylglucosamine | url = http://www.fasebj.org/cgi/content/full/15/11/1865 | journal = The FASEB Journal | volume = 15 | issue = 11| pages = 1865–1876 | doi=10.1096/fj.01-0094rev| pmid = 11532966 | citeseerx = 10.1.1.324.6370 }} 2 : Metabolism|Coenzymes |
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