N-Acetylglucosamine
Oxford Dictionary of Biochemistry:
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N-acetylglucosamine
symbol: d-GlcpNAc; abbr.: NAG; the d isomer, 2-acetamido-2-deoxy-d-glucopyranose, is a common structural unit of plant glycoproteins and of many animal and bacterial glycoproteins. It is often the terminal sugar of anoligosaccharide moiety of a glycoprotein, linked glycosidically to the amide nitrogen of a protein asparagine residue. The acetyl group is introduced in a reaction between acetyl-CoA and glucosamine 6-phosphate to give N-acetylglucosamine 6-phosphate, which undergoes amutase reaction to form N-acetylglucosamine 1-phosphate, from which UDP-N-acetylglucosamine is formed. The latter is the reactant in pathways of oligosaccharide synthesis and is also a precursor of N-acetylneuraminic acid (see sialic acid).
| N-acetylgalactosaminidase, N-acetylgalactosamine-6-sulfatase, N-acetylgalactosamine-4-sulfatase | |
| N-acetylglucosamine phosphotransferase, N-acetylglucosamine-6-sulfatase, N-acetylglucosaminidase |
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N-Acetylglucosamine
| N-Acetylglucosamine | |
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2-(Acetylamino)-2-deoxy-D-glucose |
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Other names
N-Acetyl-D-Glucosamine |
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| Identifiers | |
| CAS number | 7512-17-6  |
| PubChem | 24139 |
| ChemSpider | 22563 |
| UNII | V956696549  |
| ChEBI | CHEBI:28009 |
| ChEMBL | CHEMBL447878 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C8H15NO6 |
| Molar mass | 221.21 |
| Melting point |
211 |
| Hazards | |
| S-phrases | S24/25 |
| Related compounds | |
| Related Monosaccharides | N-Acetylgalactosamine |
| Related compounds | Glucosamine Glucose |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
N-Acetylglucosamine (N-acetyl-D-glucosamine, or GlcNAc, or NAG) is a monosaccharide derivative of glucose. It is an amide between glucosamine and acetic acid. It has a molecular formula of C8H15NO6, a molar mass of 221.21 g/mol, and it is significant in several biological systems.
It is part of a biopolymer in the bacterial cell wall, built from alternating units of GlcNAc and N-acetylmuramic acid (MurNAc), cross-linked with oligopeptides at the lactic acid residue of MurNAc. This layered structure is called peptidoglycan.
GlcNAc is the monomeric unit of the polymer chitin, which forms the outer coverings of insects and crustaceans. It is the main component of the cell walls of fungi, the radulas of mollusks, and the beaks of cephalopods.
Polymerized with glucuronic acid, it forms hyaluronan.
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Contents
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Medical uses
It has been proposed as a treatment for autoimmune diseases,[1] and recent tests have claimed some success.[2]
See also
- Keratan sulfate
- Chitin
- N-acetyllactosamine synthase
- Wheat germ agglutinin, a plant lectin that binds to this substrate
References
- ^ "Sugar supplement may treat immune disease - health - 07 June 2007 - New Scientist". http://www.newscientist.com/channel/health/mg19426074.500?DCMP=NLC-nletter&nsref=mg19426074.500. Retrieved 2007-06-08.
- ^ "Glucosamine-Like Supplement Suppresses Multiple Sclerosis Attacks, Study Suggests". Science Daily. http://www.sciencedaily.com/releases/2011/09/110930123057.htm.
External links
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Oxford Dictionary of Biochemistry
Oxford University Press. Oxford Dictionary of Biochemistry and Molecular Biology © 1997, 2000, 2006 All rights reserved.
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