N-Acetylglucosamine
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N-Acetylglucosamine (N-Acetyl-D-Glucosamine, or GlcNAc, or NAG) is a monosaccharide derivative of glucose with formula weight 221.21 amu. Chemically it is an amide between glucosamine and acetic acid.
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.
N-acetylglucosamine is the monomeric unit of the polymer chitin, which forms the exoskeleton of insects.
NAG is also of note in neurotransmission, where it is thought to be an atypical neurotransmitter functioning in nocioceptive (pain) pathways.
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