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beta-N-Acetylglucosamine (PC000168)

Record Information
Version1.0
Creation date2015-10-09 22:29:01 UTC
Update date2017-01-19 02:36:15 UTC
FoodComEx IDPC000168
FoodDB RecordFDB022253
Chemical Information
Namebeta-N-Acetylglucosamine
DescriptionAll animals and plants dynamically attach and remove beta-N-acetylglucosamine at serine and threonine residues on myriad nuclear and cytoplasmic proteins. b-N-Acetylglucosamine cycling, which is tightly regulated by the concerted actions of two highly conserved enzymes, serves as a nutrient and stress sensor. On some proteins, b-N-Acetylglucosamine competes directly with phosphate for serine/threonine residues. b-N-Acetylglucosamine's subcellular localization in hepatocytes established that it is highly concentrated at the nuclear envelope, particularly at the nuclear pore complex, but is also abundant and widespread within chromatin. However, several cytosolic and cytoskeletal proteins are also found to be glycosylated with b-N-Acetylglucosamine. b-N-Acetylglucosamination is in many ways distinct from 'classical' protein glycosylation. First, it is found mostly within the cytoplasm or nucleoplasm. Second, unlike the extraordinarily complex array of glycans found on extracellular glycoproteins, b-N-Acetylglucosamine is not elongated or further modified. Third, b-N-Acetylglucosamine cycles by means of mechanisms and on a timescale similar to those of phosphorylation and quite different from the cycling of complex extracellular glycans. b-N-Acetylglucosamination is one of the most common post-translational modifications. In terms of high-energy compounds, the intracellular concentration of the direct donor for b-N-Acetylglucosamination, UDP-GlcNAc, is second only to that of ATP, with 2-5% of all glucose being used to generate this sugar nucleotide. b-N-Acetylglucosaminated proteins can be found in almost every intracellular compartment, and there are proteins in almost every functional class that are subject to b-N-Acetylglucosamination. (PMID: 17460662) [HMDB]
CAS Number14131-68-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
2-Acetamido-2-deoxy-b-D-glucosehmdb
2-Acetamido-2-deoxy-beta-D-glucosehmdb
2-Acetamido-2-deoxy-beta-delta-glucosehmdb
b-N-Acetyl-D-glucosaminehmdb
b-N-Acetylglucosaminehmdb
beta-N-Acetyl-D-glucosaminehmdb
beta-N-Acetyl-delta-glucosaminehmdb
beta-N-Acetylglucosaminehmdb
BetaGlcNAcChEBI
GlcNAc-bGenerator
GlcNAc-betaChEBI
GlcNAc-βGenerator
N-Acetyl-b-D-glucosaminehmdb
N-Acetyl-beta-D-glucosaminehmdb
N-Acetyl-β-D-glucosamineGenerator
Chemical FormulaC8H15NO6
IUPAC nameN-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
InChI IdentifierInChI=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
InChI KeyOVRNDRQMDRJTHS-FMDGEEDCSA-N
Isomeric SMILESCC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O
Average Molecular Weight221.2078
Monoisotopic Molecular Weight221.089937217
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Hexose monosaccharide
  • Monosaccharide
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 1 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Not Available