N,N′-Diacetylchitobiose

• Catalog No.: 31538
• CAS Number: 35061-50-8
• M. F.: C16H28N2O11
• M. W.: 424.40032
• Purity: ≥96.0% (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
• MDL Number: MFCD00077715
• Beilstein Number: 61689

PROPERTIES

• Empirical Formula (Hill Notation): C16H28N2O11
• Purity: ≥96.0% (HPLC)
• Melting Point: 245-247 °C(lit.)
• Solubility: H2O: soluble50 mg/mL, clear, colorless
• 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.
Other Notes
Binding characteristics of N-acetylglucosamine-specific lectin on isolated chicken hepatocytes1; Characterization of a chito-oligosaccharide-specific lectin from the exudate of ridge gourd2
Preparation Note
by the procedure of S.A. Barker et al., J. Chem. Soc. 2218 (1958)

Description (简体中文)

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.
Other Notes
Binding characteristics of N-acetylglucosamine-specific lectin on isolated chicken hepatocytes1; Characterization of a chito-oligosaccharide-specific lectin from the exudate of ridge gourd2
Preparation Note
by the procedure of S.A. Barker et al., J. Chem. Soc. 2218 (1958)