D1523

N,N′-Diacetylchitobiose

≥96% (HPLC)

• Sinônimo(s): 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 (Notação de Hill): C₁₆H₂₈N₂O₁₁
• Número CAS: 35061-50-8
• Peso molecular: 424.40
• Beilstein: 61689
• Número MDL: MFCD00077715
• Código UNSPSC: 12352201
• ID de substância PubChem: 24893467
• NACRES: NA.25

Propriedades

• Nível de qualidade: 200
• Ensaio: ≥96% (HPLC)
• forma: powder
• atividade óptica: [α]/D 15.00 to 19.00 °, c = 9.00-11.00 mg/mL in water
• cor: off-white
• pf: 245-247 °C (lit.)
• solubilidade: H₂O: 49.00-51.00 mg/mL, clear, colorless
• temperatura de armazenamento: −20°C
• cadeia de caracteres 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
• chave InChI: CDOJPCSDOXYJJF-CBTAGEKQSA-N

Descrição

Aplicação

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. 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).

Ações bioquímicas/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 preparo

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

Outras notas

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

Informações de segurança

• Pictogramas: GHS07
• Palavra indicadora: Warning
• Frases de perigo: H315,H319
• Declarações de precaução: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Classificações de perigo: Eye Irrit. 2 - Skin Irrit. 2
• Código de classe de armazenamento: 11 - Combustible Solids
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable
• Equipamento de proteção individual: dust mask type N95 (US), Eyeshields, Gloves