N,N′-Diacetylchitobiose

C₁₆H₂₈N₂O₁₁

424.40

61689

MFCD00077715

24893467

NA.25

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).

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.

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

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D1523.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

200

≥96% (HPLC)

powder

[α]/D 15.00 to 19.00 °, c = 9.00-11.00 mg/mL in water

245-247 ℃ (lit.)

H₂O: 49.00-51.00 mg/mL, clear, colorless

−20℃

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

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

CDOJPCSDOXYJJF-CBTAGEKQSA-N

10 mg in glass bottle

GHS07

Warning

H315 - H319

P302 + P352 - P305 + P351 + P338

Eye Irrit. 2 - Skin Irrit. 2

11 - Combustible Solids

WGK 3

dust mask type N95 (US), Eyeshields, Gloves