N-Acetylglucosamine

Source: Wikipedia, the free encyclopedia.

"GlcNAc" redirects here. Not to be confused with
GlyNAC
.
N-Acetylglucosamine

Names
IUPAC name
β-D-(Acetylamino)-2-deoxy-glucopyranose
Other names
N-Acetyl-D-glucosamine
GlcNAc
NAG
Identifiers
3D model (
JSmol
)
1247660
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.028.517 Edit this at Wikidata
EC Number
  • 231-368-2
721281
KEGG
UNII
  • InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8-/m1/s1 checkY
    Key: OVRNDRQMDRJTHS-FMDGEEDCSA-N checkY
  • InChI=1/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8-/m1/s1
    Key: OVRNDRQMDRJTHS-FMDGEEDCBL
  • O=C(N[C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@H]1O)CO)C
Properties
C8H15NO6
Molar mass 221.21
Melting point 211
Related compounds
Related Monosaccharides
 N-Acetylgalactosamine
Related compounds
 Glucosamine
Glucose
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N-Acetylglucosamine molecule

N-Acetylglucosamine (GlcNAc) is an amide derivative of the monosaccharide glucose. It is a secondary amide between glucosamine and acetic acid. It is significant in several biological systems.

It is part of a biopolymer in the bacterial

oligopeptides at the lactic acid residue of MurNAc. This layered structure is called peptidoglycan
(formerly called murein).

GlcNAc is the monomeric unit of the

fungi
.

Polymerized with glucuronic acid, it forms hyaluronan.

GlcNAc has been reported to be an inhibitor of elastase release from human polymorphonuclear leukocytes (range 8–17% inhibition), however this is much weaker than the inhibition seen with N-acetylgalactosamine (range 92–100%).[1]

Medical uses

It has been proposed as a treatment for

autoimmune diseases and recent tests have claimed some success.[2][3]

O-GlcNAcylation

Main article: O-GlcNAc

O-GlcNAcylation is the process of adding a single N-acetylglucosamine sugar to the serine or threonine of a protein.[4] Comparable to phosphorylation, addition or removal of N-acetylglucosamine is a means of activating or deactivating enzymes or transcription factors.[4] In fact, O-GlcNAcylation and phosphorylation often compete for the same serine/threonine sites.[4] O-GlcNAcylation most often occurs on chromatin proteins, and is often seen as a response to stress.[4]

spatial learning and memory improved.[6]

See also

References

  1. PMID 2054963
    .
  2. PMID 21965673
    .
  3. PMID 37705084
    .
  4. ^
    PMID 21391816
    .
  5. PMID 23992419
    .
  6. PMID 31588002
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=N-Acetylglucosamine&oldid=1179200076"