Chitobiose (PAMDB000515)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000515
Identification
Name: Chitobiose
Description:Chitobiose is a dimer of beta-1,4-linked glucosamine units. There is ambiguity as to which structure the name refers, owing to the method by which it was first isolated.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-(acetylamino)-4-O-[2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]-2-deoxy-β-D-glucopyranose
  • 2-(acetylamino)-4-O-[2-(acetylamino)-2-Deoxy-b-D-glucopyranosyl]-2-deoxy-b-D-glucopyranose
  • 2-(Acetylamino)-4-O-[2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]-2-deoxy-beta-D-glucopyranose
  • 2-(acetylamino)-4-O-[2-(acetylamino)-2-Deoxy-β-D-glucopyranosyl]-2-deoxy-β-D-glucopyranose
  • N-[2-[5-acetylamino-4,6-dihydroxy-2-(hydroxymethyl)tetrahydropyran-3-yl]oxy-4,5-dihyrdoxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide
  • CBS
  • Chitobiose
  • Chitodextrin
  • Diacetylchitobiose
  • N-[2-[5-Acetylamino-4,6-dihydroxy-2-(hydroxymethyl)tetrahydropyran-3-yl]oxy-4,5-dihyrdoxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide
Chemical Formula: C16H28N2O11
Average Molecular Weight: 424.403
Monoisotopic Molecular Weight: 424.16930973
InChI Key: CDOJPCSDOXYJJF-CBTAGEKQSA-N
InChI:InChI=1S/C16H28N2O11/c1-5(21)17-9-13(25)14(8(4-20)27-15(9)26)29-16-10(18-6(2)22)12(24)11(23)7(3-19)28-16/h7-16,19-20,23-26H,3-4H2,1-2H3,(H,17,21)(H,18,22)/t7-,8-,9-,10-,11-,12-,13-,14-,15?,16+/m1/s1
CAS number: 577-76-4
IUPAC Name:N-[(3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional IUPAC Name: N,N-diacetylchitobiose
SMILES:CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)[C@@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassOrganic oxygen compounds
Class Organooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct Parent Acylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Acetamide
  • 1,2-diol
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Acetal
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organonitrogen compound
  • Alcohol
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility111.0 mg/mLALOGPS
logP-2.6ALOGPS
logP-5.3ChemAxon
logS-0.58ALOGPS
pKa (Strongest Acidic)11.5ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area207.27 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity90.54 m3·mol-1ChemAxon
Polarizability40.89 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Phosphoenolpyruvic acid + Chitobiose > Diacetylchitobiose-6-phosphate + Pyruvic acid
Chitobiose + Water <>2 N-Acetyl-D-glucosamine
Water + Chitobiose + Chitobiose >2 N-Acetyl-D-glucosamine +2 N-Acetylglucosamine
Chitin + Water > Chitobiose + Chitin + Chitobiose
Pathways:
  • Amino sugar and nucleotide sugar metabolism pae00520
Spectra
Spectra:
References
References:
  • Collin M, Olsen A: EndoS, a novel secreted protein from Streptococcus pyogenes with endoglycosidase activity on human IgG. EMBO J. 2001 Jun 15;20(12):3046-55. Pubmed: 11406581
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Nimtz M, Grabenhorst E, Gambert U, Costa J, Wray V, Morr M, Thiem J, Conradt HS: In vitro alpha1-3 or alpha1-4 fucosylation of type I and II oligosaccharides with secreted forms of recombinant human fucosyltransferases III and VI. Glycoconj J. 1998 Sep;15(9):873-83. Pubmed: 10052591
  • van Pelt J, Hard K, Kamerling JP, Vliegenthart JF, Reuser AJ, Galjaard H: Isolation and structural characterization of twenty-one sialyloligosaccharides from galactosialidosis urine. An intact N,N'-diacetylchitobiose unit at the reducing end of a diantennary structure. Biol Chem Hoppe Seyler. 1989 Mar;370(3):191-203. Pubmed: 2713102
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Cottaz, Sylvain; Samain, Eric. Genetic engineering of Escherichia coli for the production of NI,NII-diacetylchitobiose (chitinbiose) and its utilization as a primer for the synthesis of complex carbohydrates. Metabolic Engineering (2005), 7(4), 311
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID28681
HMDB IDHMDB03556
Pubchem Compound ID656440
Kegg IDC01674
ChemSpider ID17216232
WikipediaChitobiose
BioCyc IDCHITOBIOSE
EcoCyc IDCHITOBIOSE

Enzymes

Protein Details
• Beta-hexosaminidase
General function:
Involved in beta-N-acetylhexosaminidase activity
Specific function:
Cleaves GlcNAc linked beta-1,4 to MurNAc tripeptides
Gene Name:
nagZ
Locus Tag:
PA3005
Molecular weight:
36.1 kDa
Reactions
Hydrolysis of terminal non-reducing N-acetyl-D-hexosamine residues in N-acetyl-beta-D-hexosaminides.

Transporters