- 同
- UDP-GlcNAc
WordNet
- the 14th letter of the Roman alphabet (同)n
PrepTutorEJDIC
- nitrogenの化学記号
- neodymiumの化学記号
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/20 16:14:48」(JST)
[Wiki en表示]
Uridine diphosphate N-acetylglucosamine
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| Names |
| IUPAC name
[(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
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| Other names
UDP-N-acetylglucosamine; UDP-GlcNAc
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| Identifiers |
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CAS Number
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91183-98-1 N |
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IUPHAR/BPS
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1779 |
| Jmol 3D model |
Interactive image |
| PubChem |
445675 |
SMILES
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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
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| Properties |
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Chemical formula
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C17H27N3O17P2 |
| Molar mass |
607.35 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| N verify (what is YN ?) |
| Infobox references |
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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.
References
- ^ Roseman, S (2001). "Reflections on glycobiology". The Journal of Biological Chemistry 276 (45): 41527–42. doi:10.1074/jbc.R100053200. PMID 11553646.
- ^ Sudhamoy Ghosh; Blumenthal, HJ; Davidson, E; Roseman, S (1960-05-01). "Glucosamine Metabolism". Journal of Biological Chemistry 235 (5): 1265–73. PMID 13827775.
- ^ International Union of Biochemistry and Molecular Biology
- ^ Milewski S, Gabriel I, Olchowy J (2006). "Enzymes of UDP-GlcNAc biosynthesis in yeast". Yeast 23 (1): 1–14. doi:10.1002/yea.1337. PMID 16408321.
- ^ Hanover, J. A. (2001). "Glycan-dependent signaling: O-linked N-acetylglucosamine". The FASEB Journal 15: 1865–1876. doi:10.1096/fj.01-0094rev.
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Types of nucleotide sugars
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- CDP-glucose
- GDP-mannose
- TDP-glucose
- UDP-glucose
- UDP-galactose
- UDP-glucuronic acid
- UDP-N-acetylglucosamine
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UpToDate Contents
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English Journal
- New insights: A role for O-GlcNAcylation in diabetic complications.
- Peterson SB1, Hart GW1.
- Critical reviews in biochemistry and molecular biology.Crit Rev Biochem Mol Biol.2016 Jan 24:1-12. [Epub ahead of print]
- Diabetes is a debilitating metabolic disease that is riddled with complications that can cause blindness, renal failure, nerve damage, and cardiovascular disease. Poor glycemic control is thought to be a key initiator in the progression of diabetic complications. Hyperglycemia has been shown to incr
- PMID 26806492
- Biophysical characterization and activity of lymphostatin, a multifunctional virulence factor of attaching & effacing Escherichia coli.
- Cassady-Cain RL1, Blackburn EA2, Alsarraf H3, Dedic E3, Bease AG1, Böttcher B2, Jørgensen R3, Wear M2, Stevens MP4.
- The Journal of biological chemistry.J Biol Chem.2016 Jan 19. pii: jbc.M115.709600. [Epub ahead of print]
- Attaching & effacing Escherichia coli cause diarrhoea and typically produce lymphostatin (LifA), an inhibitor of mitogen-activated proliferation of lymphocytes and pro-inflammatory cytokine synthesis. A near-identical factor (Efa1) has been reported to mediate adherence of E. coli to epithelial
- PMID 26786100
- Characterizing non-hydrolyzing Neisseria meningitidis serogroup A UDP-N-acetylglucosamine (UDP-GlcNAc) 2-epimerase using UDP-N-acetylmannosamine (UDP-ManNAc) and derivatives.
- Zhang L1, Muthana MM1, Yu H1, McArthur JB1, Qu J1, Chen X2.
- Carbohydrate research.Carbohydr Res.2016 Jan;419:18-28. doi: 10.1016/j.carres.2015.10.016. Epub 2015 Nov 5.
- Neisseria meningitidis serogroup A non-hydrolyzing uridine 5'-diphosphate-N-acetylglucosamine (UDP-GlcNAc) 2-epimerase (NmSacA) catalyzes the interconversion between UDP-GlcNAc and uridine 5'-diphosphate-N-acetylmannosamine (UDP-ManNAc). It is a key enzyme involved in the biosynthesis of the capsula
- PMID 26598987
Japanese Journal
- Effects of exercise on the hexosamine biosynthetic pathway and glycosylation
- Shirato Ken,Kizaki Takako,Ohno Hideki,Imaizumi Kazuhiko
- The Journal of Physical Fitness and Sports Medicine 1(1), 145-150, 2012
- … Minor amounts of glucose incorporated into the cells is metabolized via the hexosamine biosynthetic pathway, resulting in the production of uridine-5'-diphosphate-N-acetylglucosamine (UDP-GlcNAc), which is utilized as a donor substrate for the N- and O-linked glycosylation of extracellular and membrane proteins in the Golgi apparatus, or for the O-linked GlcNAc modification (O-GlcNAcylation) of intracellular proteins in the cytosol. …
- NAID 130001930777
- A mutant yeast deficient in Golgi transport of uridine diphosphate N-acetylglucosamine.
- Glycosylated DNA-Binding Proteins from Filamentous Fungus, Aspergillus oryzae : Modification with N-Acetylglucosamine Monosaccharide through an O-Glycosidic Linkage
- Machida Masayuki,Jigami Yoshifumi
- Ｂｉｏｓｃｉｅｎｃｅ， Ｂｉｏｔｅｃｈｎｏｌｏｇｙ， ａｎｄ Ｂｉｏｃｈｅｍｉｓｔｒｙ 58(2), 344-348, 1994-02-23
- … The labeling of the proteins by uridine 5'-diphosphate(UDP)-[^<14>C]galactose using galactosyltransferase showed the same electrophoretic pattern with the WGA-probing. … The [^<14>C]-galactose-labeled saccharides were released from the proteins by mild-base treatment but not by N-glyco-peptidase F digestion, indicating the O-glycosidic linkage of the saccharide chain attachment to proteins. …
- NAID 110002676817
Related Links
- "Uridine Diphosphate N-Acetylglucosamine" is a descriptor in the National Library of Medicine's controlled vocabulary thesaurus, MeSH (Medical Subject Headings). Descriptors are arranged in a hierarchical structure, which enables ...
- 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 ...
★リンクテーブル★
[★]
- 英
- uridine diphosphate N-acetylglucosamine
[★]
二リン酸エステル、二リン酸塩、二リン酸
- 関
- bisphosphate、diphosphoric acid、pyrophosphate
[★]
- 関
- number of experiment、sample size
- pの前の[n]はmと記載する。synptom→symptom
[★]
[★]
アセチルグルコサミン
- 関
- N-acetyl-D-glucosamine
[★]
ネオジム neodymium