N-Acetylglucosamine

  • N-acetyl -D-glucosamine
  • 2 -acetamido- 2-deoxy- D- glucopyranose
  • 2 - ( acetylamino )-2- deoxy -D-glucose (IUPAC)
  • GlcNAc
  • NAG

Odorless, white to off-white crystalline powder

Fixed

195-215 ° C

Slightly soluble in water

Template: Infobox chemical / molecular formula search available

N-acetylglucosamine is a monosaccharide and a derivative of D-glucose, which has an amide group at the position acetylated two of the ring.

Properties

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

Biological Significance

N -acetyl-glucosamine is part of the biopolymers in the cell wall of bacteria which ( MurNAc ) is constructed with cross-linked oligopeptides the lactic acid moiety of MurNAc of alternating units of N -acetylglucosamine and N- acetylmuramic acid. This layer structure is called peptidoglycan. Also in archaea it is an important component of the cell wall ( Pseudopeptidoglycan ). N-acetylglucosamine is also the monomer of the polymer, chitin, of which the outer shells of insects and crustaceans are constructed.

Naturally occurring in the body D -glucosamine component of cartilage and the synovial fluid is fluid (joint fluid ). More specifically, the N-acetyl -D-glucosamine in the polysaccharide part of the hyaluronic acid, the " lubricant " of the joints and the backbone of the proteoglycans, an integral part of the cartilage. In proteoglycan and of the cornea and the keratan sulfate chains are present, which is also made ​​up of N- acetyl-D- glucosamine. In other glycoproteins N-acetyl- D-glucosamine plays a major role in the core structure of N - glycans as well as in the antennas of N- glycans and O- glycans.

As a common feature of all blood groups occur as N- acetylglucosamine present in the glycocalyx of the erythrocytes. It binds galactose. At the galactose fucose is not bound. These form the blood group 0 or the " family tree " of all blood types. In addition to the galactose nor N -acetylgalactosamine (blood group A) or another galactose bind (blood group B).

CAS registry number PubChem
27002
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