N,N′-Diacetylchitobiose

• Catalog No.: D1523
• CAS Number: 35061-50-8
• M. F.: C16H28N2O11
• M. W.: 424.40032
• Purity: ≥96% (HPLC)

SYNONYMS

• IUPAC name: N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: Chitobiose; 2-Acetamido-2-deoxy-4-O-(2-acetamido-2-deoxy-β-D-gluco-pyranosyl)-D-glucopyranose; 4-O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-2-acetamido-2-deoxy-D-glucose

DATABASE IDS

• CAS Number: 35061-50-8
• PubChem SID: 24893467
• MDL Number: MFCD00077715
• Beilstein Number: 61689

PROPERTIES

• Purity: ≥96% (HPLC)
• Melting Point: 245-247 °C(lit.)
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319
• European Hazard Symbols: Irritant (Xi)
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• GHS Precautionary statements: P305 + P351 + P338
• Risk Statements: 36/38
• Safety Statements: 26-36
• Storage Temperature: -20°C
• German water hazard class: 3

DETAILS

Description (English)

Biochem/physiol Actions
In chitinolytic bacteria, such as Vibrio, Streptomyces and Serratia, N,N′-Diacetylchitobiose (GlcNAc2) is not only a major breakdown product of chitinase, but it is also the smallest substance that induces chitinase production. It can also be utilized as a carbon source by E. coli, which does not express chitinases, but is exposed to GlcNAc2 produced by intestinal chitinolytic bacteria. In most organisms, the uptake of GlcNAc2 occurs via the phosphoenolpyruvate:glycose phosphotransferase system (PTS). GlcNAc2 has also been used as a substrate or inhibitor to study the activity of glycolytic enzymes.
Preparation Note
Prepared by the method of Barker, S.A., et al., J. Chem. Soc., 2218 (1958).
Application
Diacetylchitobiose/Chitobiose, a dimer of β(1,4) linked N-acetyl-D glucosamine, is used as an alternative source of N-acetylglucosamine by some bacteria. Chitobiose is used to study and differentiate chitobiose transporter systems and enzymes such as β-N-acetylglucosaminidase(s) and chitobiose phosphorylase(s).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D1523.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.