D1523

N,N′-Diacetylchitobiose

≥96% (HPLC)

• Sinónimos: 2-Acetamido-2-deoxy-4-O-(2-acetamido-2-deoxy-β-D-gluco­pyranosyl)-D-glucopyranose, 4-O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-2-acetamido-2-deoxy-D-glucose, Chitobiose
• Fórmula empírica (notación de Hill): C₁₆H₂₈N₂O₁₁
• Número de CAS: 35061-50-8
• Peso molecular: 424.40
• Beilstein: 61689
• Número MDL: MFCD00077715
• Código UNSPSC: 12352201
• ID de la sustancia en PubChem: 24893467
• NACRES: NA.25

Propiedades

• Nivel de calidad: 200
• Ensayo: ≥96% (HPLC)
• Formulario: powder
• actividad óptica: [α]/D 15.00 to 19.00 °, c = 9.00-11.00 mg/mL in water
• color: off-white
• mp: 245-247 °C (lit.)
• solubilidad: H₂O: 49.00-51.00 mg/mL, clear, colorless
• temp. de almacenamiento: −20°C
• cadena 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
• 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
• Clave InChI: CDOJPCSDOXYJJF-CBTAGEKQSA-N

Descripción

Aplicación

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]

Acciones bioquímicas o fisiológicas

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.

Nota de preparación

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

Otras notas

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

Información de seguridad

• Pictogramas: GHS07
• Palabra de señalización: Warning
• Frases de peligro: H315,H319
• Consejos de prudencia: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Clasificaciones de peligro: Eye Irrit. 2 - Skin Irrit. 2
• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable
• Equipo de protección personal: dust mask type N95 (US), Eyeshields, Gloves