N -acetylglucosamine

Structural formula
General
Surname	N-acetylglucosamine
other names	N -acetyl- D -glucosamine; 2-acetamido-2-deoxy- D- glucopyranose; 2- (Acetylamino) -2-deoxy- D -glucose ( IUPAC ); GlcNAc; NAG;
Molecular formula	C 8 H 15 NO 6
Brief description	odorless, white to off-white, crystalline powder
External identifiers / databases
EC number	231-368-2
ECHA InfoCard	100.028.517
PubChem	24139
ChemSpider	22563
DrugBank	DB00141
Wikidata	Q284367
properties
Molar mass	221.21 g mol −1
Physical state	firmly
Melting point	195-215 ° C
solubility	easily soluble in water
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

N -acetylglucosamine is a monosaccharide and a derivative of D - glucose , which has an acetylated amine residue in position 2 of the ring.

properties

N -acetylglucosamine is an odorless, white to off-white, crystalline powder. It is the amide of glucosamine and acetic acid . When polymerized with glucuronic acid , it forms hyaluronic acid , which belongs to the glycosaminoglycans or heteroglycans .

Biological importance

N -acetylglucosamine is part of the biopolymers in the cell wall of bacteria , which is built from alternating units of N -acetylglucosamine and N -acetylmuramic acid (MurNAc), linked with oligopeptides on the lactic acid residue of MurNAc. This layer structure is also called peptidoglycan . Also in archaea it is an important part of the cell wall ( pseudopeptidoglycan ). N- acetylglucosamine is also the monomer unit of the polymer chitin , from which the outer shells of insects and crabs are built.

D- glucosamine, which occurs naturally in the body, is part of the cartilage and synovial fluid (joint fluid). More precisely, the N -acetyl- D -glucosamine is part of the polysaccharide chain of hyaluronic acid , the “lubricant” of the joints and backbone of the proteoglycan , an integral part of cartilage. In the proteoglycan and in the cornea there are also chains of keratan sulfate , which is also made up of N -acetyl- D -glucosamine. In other glycoproteins , N -acetyl- D- glucosamine plays an important role in the core structure of N -glycans and in the antennae of N -glycans and O -glycans .

As a common characteristic of all blood groups , it occurs as N- acetylglucosamine in the glycocalix of the erythrocytes . Galactose binds to it . Fucose is still bound to the galactose . These form blood group 0 or the "family tree" of all blood groups. In addition, N- acetylgalactosamine (blood group A) or another galactose (blood group B) can bind to the galactose.

Web links

Use of glucosamine and its compounds in food supplements - BfR Opinion No. 031/2007 of June 15, 2007 (PDF; 112 kB)

Individual evidence

↑ ^a ^b ^c ^d ^e Data sheet N-Acetylglucosamine (PDF) from Carl Roth , accessed on December 19, 2012.
↑ Georg Löffler, Petro E. Petrides, Peter C. Heinrich (Eds.): Biochemistry and Pathobiochemistry. 8th, completely revised edition. Springer-Medizin-Verlag, Heidelberg 2007, ISBN 978-3-540-32680-9 .

[roth-1] Data sheet N-Acetylglucosamine (PDF) from Carl Roth , accessed on December 19, 2012.

[2] Georg Löffler, Petro E. Petrides, Peter C. Heinrich (Eds.): Biochemistry and Pathobiochemistry. 8th, completely revised edition. Springer-Medizin-Verlag, Heidelberg 2007, ISBN 978-3-540-32680-9 .