N-Acetylglucosamine
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| N-Acetylglucosamine | |
|---|---|
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| IUPAC name | 2-(Acetylamino)-2-deoxy-D-glucose |
| Other names | N-Acetyl-D-Glucosamine GlcNAc NAG |
| Molecular formula | C8H15NO6 |
| Identifiers | |
| CAS number | [] |
| PubChem | |
| SMILES | [H][C@](C([H])(CO)O[C@@](O)([H])[C@@](NC(C)=O)1[H])(O)[C@@]1(O)[H] |
| Properties | |
| Molar mass | 221.21 |
| Melting point |
211 |
| Hazards | |
| S-phrases | S24/25 |
| Related Compounds | |
| Related Monosaccharides | N-Acetylgalactosamine |
| Related compounds | Glucosamine Glucose |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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N-Acetylglucosamine (N-Acetyl-D-Glucosamine, or GlcNAc, or NAG) is a monosaccharide derivative of glucose. Chemically 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. GlcNAc is also of note in neurotransmission, where it is thought to be an atypical neurotransmitter functioning in nocioceptive (pain) pathways.
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