D1523

N,N′-Diacetylchitobiose

≥96% (HPLC)

• Synonym(e): 4-O-(2-Acetamino-2-deoxy-β-D-glucopyranosyl)-2-acetamino-2-deoxy-D-glucose
• Empirische Formel (Hill-System): C₁₆H₂₈N₂O₁₁
• CAS-Nummer: 35061-50-8
• Molekulargewicht: 424.40
• Beilstein: 61689
• MDL-Nummer: MFCD00077715
• UNSPSC-Code: 12352201
• PubChem Substanz-ID: 24893467
• NACRES: NA.25

Eigenschaften

• Qualitätsniveau: 200
• Assay: ≥96% (HPLC)
• Form: powder
• Optische Aktivität: [α]/D 15.00 to 19.00 °, c = 9.00-11.00 mg/mL in water
• Farbe: off-white
• mp (Schmelzpunkt): 245-247 °C (lit.)
• Löslichkeit: H₂O: 49.00-51.00 mg/mL, clear, colorless
• Lagertemp.: −20°C
• SMILES String: 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
• 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
• InChIKey: CDOJPCSDOXYJJF-CBTAGEKQSA-N

Beschreibung

Anwendung

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.[1] It is used in fermentation research to study, differentiate and characterize chitobiose transporter systems and enzymes such as β-N-acetylglucosaminidase(s) and chitobiose phosphorylase(s).[2][3]

Biochem./physiol. Wirkung

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.

Angaben zur Herstellung

Prepared by the method of Barker, S.A., et al., J. Chem. Soc., 2218 (1958).

Sonstige Hinweise

To gain a comprehensive understanding of our extensive range of Disaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H315,H319
• P-Sätze: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Gefahreneinstufungen: Eye Irrit. 2 - Skin Irrit. 2
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: dust mask type N95 (US), Eyeshields, Gloves