同: UDP-GlcNAc

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the 14th letter of the Roman alphabet (同)n

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nitrogenの化学記号
neodymiumの化学記号

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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)

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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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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.

ABEIJON C.
J. Biol. Chem. 271, 8851-8854, 1996
NAID 80009003853

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

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リンク元	「ウリジン二リン酸-N-アセチルグルコサミン」
関連記事	「diphosphate」「n」「N」「acetylglucosamine」「Nd」

「ウリジン二リン酸-N-アセチルグルコサミン」

Uridine diphosphate N-acetylglucosamine
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
	Other names UDP-N-acetylglucosamine; UDP-GlcNAc
Identifiers
CAS Number	91183-98-1
IUPHAR/BPS	1779
Jmol 3D model	Interactive image
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 ;
Properties
Chemical formula	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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