D1523

N,N′-Diacetylchitobiose

≥96% (HPLC)

• Synonyme(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
• Formule empirique (notation de Hill): C₁₆H₂₈N₂O₁₁
• Numéro CAS: 35061-50-8
• Poids moléculaire : 424.40
• Numéro Beilstein : 61689
• Numéro MDL: MFCD00077715
• Code UNSPSC : 12352201
• ID de substance PubChem : 24893467
• Nomenclature NACRES : NA.25

Propriétés

• Niveau de qualité: 200
• Pureté: ≥96% (HPLC)
• Forme: powder
• Activité optique: [α]/D 15.00 to 19.00 °, c = 9.00-11.00 mg/mL in water
• Couleur: off-white
• Pf: 245-247 °C (lit.)
• Solubilité: H₂O: 49.00-51.00 mg/mL, clear, colorless
• Température de stockage: −20°C
• Chaîne 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
• Clé InChI: CDOJPCSDOXYJJF-CBTAGEKQSA-N

Description

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. 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).

Actions biochimiques/physiologiques

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.

Notes préparatoires

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

Autres remarques

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

Informations sur la sécurité

• Pictogrammes: GHS07
• Mention d'avertissement: Warning
• Mentions de danger: H315,H319
• Conseils de prudence: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Classification des risques: Eye Irrit. 2 - Skin Irrit. 2
• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: dust mask type N95 (US), Eyeshields, Gloves