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N,N′-Diacetylchitobiose (CAS 35061-50-8)

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Alternate Names:
GlcNAc-b-1,4-GlcNAc
Application:
N,N′-Diacetylchitobiose is a major breakdown product of chitinase and smallest substance that induces chitinase
CAS Number:
35061-50-8
Purity:
≥98%
Molecular Weight:
424.40
Molecular Formula:
C16H28N2O11
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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N,N′-Diacetylchitobiose, also referred to as N,N′-diacetylchitin, is a naturally occurring disaccharide encountered in the cell walls of fungi, bacteria, and plants. Composed of two glucose molecules linked by a glycosidic bond, it assumes a vital role in maintaining cell wall integrity and stability. Due to its potential applications in biochemistry and pharmaceuticals, N,N′-diacetylchitobiose has been extensively investigated within the scientific community. In chitinolytic bacteria, such as Vibrio, Streptomyces and Serratia N,N′-Diacetylchitobiose is not only a major breakdown product of chitinase, but the smallest substance that induces chitinase production. N,N′-Diacetylchitobiose can be utilized as a carbon source by E. coli which does not express chitinases, but is exposed to GlcNAc. The compound has been produced by intestinal chitinolytic bacteria. N,N′-Diacetylchitobiose has also, has been used as a substrate or inhibitor in the study of the activity of glycolytic enzymes. The unique properties and potential applications of N,N′-diacetylchitobiose have made it widely employed in scientific research. It has contributed to the understanding of cell wall integrity and structure, cell signaling pathways, metabolic pathways, enzyme inhibition, drug delivery, and the exploration of cancer and other diseases. By establishing a robust covalent bond between the two glucose molecules, N,N′-diacetylchitobiose is believed to exert its influence on cell wall integrity and stability. This bond assumes a role in upholding the structure of the cell wall, protecting it from damage or destruction. Additionally, N,N′-diacetylchitobiose is thought to participate in the regulation of cell signaling pathways and metabolic pathways, further highlighting its significance.


N,N′-Diacetylchitobiose (CAS 35061-50-8) References

  1. The chitin disaccharide, N,N'-diacetylchitobiose, is catabolized by Escherichia coli and is transported/phosphorylated by the phosphoenolpyruvate:glycose phosphotransferase system.  |  Keyhani, NO., et al. 2000. J Biol Chem. 275: 33084-90. PMID: 10913117
  2. Site-specific labeling of cytoplasmic peptide:N-glycanase by N,N'-diacetylchitobiose-related compounds.  |  Suzuki, T., et al. 2006. J Biol Chem. 281: 22152-22160. PMID: 16740630
  3. N,N'-diacetylchitobiose, an inhibitor of lysozyme, reverses myocardial depression and lessens norepinephrine requirements in Escherichia coli sepsis in dogs.  |  Mink, SN., et al. 2008. Shock. 29: 681-7. PMID: 17885642
  4. The importance of chitobiase and N-acetylglucosamine (GlcNAc) uptake in N,N'-diacetylchitobiose [(GlcNAc)2] utilization by Serratia marcescens 2,170.  |  Toratani, T., et al. 2008. Microbiology (Reading). 154: 1326-1332. PMID: 18451041
  5. The msiK gene, encoding the ATP-hydrolysing component of N,N'-diacetylchitobiose ABC transporters, is essential for induction of chitinase production in Streptomyces coelicolor A3(2).  |  Saito, A., et al. 2008. Microbiology (Reading). 154: 3358-3365. PMID: 18957589
  6. Molecular design of N-linked tetravalent glycosides bearing N-acetylglucosamine, N,N'-diacetylchitobiose and N-acetyllactosamine: Analysis of cross-linking activities with WGA and ECA lectins.  |  Masaka, R., et al. 2010. Bioorg Med Chem. 18: 621-9. PMID: 20056550
  7. Crystal morphology study of N,N'-diacetylchitobiose by molecular dynamics simulation.  |  Yang, L. and Dong, Y. 2011. Carbohydr Res. 346: 2457-62. PMID: 21944491
  8. An optimized cocktail of chitinolytic enzymes to produce N,N'-diacetylchitobiose and N-acetyl-d-glucosamine from defatted krill by-products.  |  Chu, F., et al. 2019. Int J Biol Macromol. 133: 1029-1034. PMID: 31004644
  9. ATP-Binding Cassette Transporter Regulates N,N'-diacetylchitobiose Transportation and Chitinase Production in Trichoderma asperellum T4.  |  Liu, H., et al. 2019. Int J Mol Sci. 20: PMID: 31096671
  10. Efficient conversion of crystalline chitin to N-acetylglucosamine and N,N'-diacetylchitobiose by the enzyme cocktail produced by Paenibacillus sp. LS1.  |  Mukherjee, S., et al. 2020. Carbohydr Polym. 250: 116889. PMID: 33049827
  11. The biosynthesis of a N,N'-diacetylchitobiose containing lipid by liver microsomes. A probable dolichol pyrophosphate derivative.  |  Leloir, LF., et al. 1973. Biochem Biophys Res Commun. 52: 1285-92. PMID: 4717748
  12. Artificial glycopolypeptide conjugates: simple synthesis of lactose- and N,N'-diacetylchitobiose-substituted poly(L-glutamic acid)s through N-beta-glycoside linkages and their interaction with lectins.  |  Kobayashi, K., et al. 1997. Biochim Biophys Acta. 1336: 117-22. PMID: 9305781

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

N,N′-Diacetylchitobiose, 10 mg

sc-219291
10 mg
$252.00

N,N′-Diacetylchitobiose, 50 mg

sc-219291A
50 mg
$1056.00