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D1523 Sigma-Aldrich

N,N′-Diacetylchitobiose

≥96% (HPLC)

Synonym: 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

  • CAS Number 35061-50-8

  • Empirical Formula (Hill Notation) C16H28N2O11

  • Molecular Weight 424.40

  •  Beilstein/REAXYS Number 61689

  •  MDL number MFCD00077715

  •  PubChem Substance ID 24893467

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Properties

Related Categories Biochemicals and Reagents, Carbohydrates, Carbohydrates A to Z, Carbohydrates D-F, Disaccharide More...
InChI Key   CDOJPCSDOXYJJF-CBTAGEKQSA-N
assay   ≥96% (HPLC)
mp   245-247 °C (lit.)
solubility   H2O: 49.00-51.00 mg/mL, clear, colorless
storage temp.   −20°C

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).

Packaging

10 mg in glass bottle

Biochem/physiol Actions

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.

Preparation Note

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

Other Notes

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.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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92210 Timestrip Plus 0 °C
06693 Timestrip Plus -20 °C

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