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Chemical Compound Review

CHEBI:50678     (2R,3R,4R,5R)-2-amino-4- [(2R,3R,4R,5S,6R)...

Synonyms: AR-1D8385, AC1L3U3J, AC1Q6A6B
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Disease relevance of chitobiose


High impact information on chitobiose

  • Inclusion of anti-beta1-subunit antibody or chitobiose in cell aggregation assays using mouse neural cells resulted in inhibition of cell aggregation [6].
  • This study describes the discovery of a new inherited disorder of glycosylation named "CDG-Ik." CDG-Ik (congenital disorder of glycoslyation type Ik) is based on a defect of human mannosyltransferase I (MT-I [MIM 605907]), an enzyme necessary for the elongation of dolichol-linked chitobiose during N-glycan biosynthesis [7].
  • The acylation activity was sensitive to oligosaccharide chain length, with chitotetraose serving as a better substrate than chitobiose or chitotriose [8].
  • These results suggest that cytoplasmic PNGase has a separate binding site for chitobiose and other carbohydrates, and haloacetamide derivatives can irreversibly inhibit that catalytic Cys in a highly specific manner [9].
  • Given that Fbs proteins interact with innermost chitobiose in N-glycans, we propose that Fbs proteins distinguish native from unfolded glycoproteins by sensing the exposed chitobiose structure [10].

Chemical compound and disease context of chitobiose


Biological context of chitobiose

  • Molecular modeling of N,N'-diacetylchitobiose (chitobiose) binding to the protein suggests that the carbohydrate binding site is distinct from but adjacent to that of Z-VAD-fmk, a peptide-based inhibitor of this enzyme [9].
  • ChbR is necessary for transcription activation in the presence of chitobiose in vivo [2].
  • Hydrolysis patterns on chitooligosaccharides indicated that ChiB is a chitobiosidase, processively cleaving off chitobiose from the nonreducing end of chitin or other chitooligomers [15].
  • [reaction: see text] Herein we apply a recently introduced protocol using ammonium carbamate in methanol to the amination of crude chitobiose leading to 1,beta-aminochitobiose [16].
  • The reaction product of chitobiose after the acetylation reaction was exclusively 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1-->4)-2-amino-2-deoxy-D-gluc ose [GlcNAcGlcN], the structure of which was determined by FABMS and NMR analyses [17].

Anatomical context of chitobiose

  • The major storage pentasaccharide from both normal and affected swainsonine-treated fibroblasts was sensitive to digestion with alpha-mannosidase and endo-beta-N-acetylhexosaminidase D, suggesting a branched mannose structure and a chitobiose core [18].
  • NKR-P1A protein, an activating receptor of rat natural killer cells, binds to the chitobiose core of uncompletely glycosylated N-linked glycans, and to linear chitooligomers [19].
  • Limited proteolysis of rough microsomes decreased the GTP-binding capacity and prevented GTP from suppressing the latency of mannose-6-phosphatase and of the synthesis of dolichol-linked chitobiose [20].

Associations of chitobiose with other chemical compounds


Gene context of chitobiose

  • Effect of the Met344His mutation on the conformational dynamics of bovine beta-1,4-galactosyltransferase: crystal structure of the Met344His mutant in complex with chitobiose [24].
  • Chitobiose is transported by the phosphotransferase system (PTS) producing chitobiose-6P which is hydrolysed to GlcNAc-6P by the chbF gene product and then further degraded by the nagBA gene products [2].
  • Approximately 9% of the biantennary complex oligosaccharides on SHBG of control men and none of those on SHBG from alcoholic men were fucosylated on the chitobiose core, as determined by chromatography on Lenn culinaris lectin [25].
  • A family of novel, acidic N-glycans in Bowes melanoma tissue plasminogen activator have L2/HNK-1-bearing antennae, many with sulfation of the fucosylated chitobiose core [26].
  • Here we report the crystal structures of the sugar-binding domain (SBD) of Fbs1 alone and in complex with chitobiose [27].

Analytical, diagnostic and therapeutic context of chitobiose


  1. Purification and characterization of an exo-beta-D-glucosaminidase, a novel type of enzyme, from Nocardia orientalis. Nanjo, F., Katsumi, R., Sakai, K. J. Biol. Chem. (1990) [Pubmed]
  2. Expression of the chitobiose operon of Escherichia coli is regulated by three transcription factors: NagC, ChbR and CAP. Plumbridge, J., Pellegrini, O. Mol. Microbiol. (2004) [Pubmed]
  3. Cell wall studies of Histoplasma capsulatum and Blastomyces dermatitidis using autologous and heterologous enzymes. Davis, T.E., Domer, J.E., Li, Y.T. Infect. Immun. (1977) [Pubmed]
  4. Bactericidal activity of human lysozyme, muramidase-inactive lysozyme, and cationic polypeptides against Streptococcus sanguis and Streptococcus faecalis: inhibition by chitin oligosaccharides. Laible, N.J., Germaine, G.R. Infect. Immun. (1985) [Pubmed]
  5. Genetics and regulation of chitobiose utilization in Borrelia burgdorferi. Tilly, K., Elias, A.F., Errett, J., Fischer, E., Iyer, R., Schwartz, I., Bono, J.L., Rosa, P. J. Bacteriol. (2001) [Pubmed]
  6. Mouse Na+/K+-ATPase beta1-subunit has a K+-dependent cell adhesion activity for beta-GlcNAc-terminating glycans. Kitamura, N., Ikekita, M., Sato, T., Akimoto, Y., Hatanaka, Y., Kawakami, H., Inomata, M., Furukawa, K. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  7. Congenital disorder of glycosylation type Ik (CDG-Ik): a defect of mannosyltransferase I. Kranz, C., Denecke, J., Lehle, L., Sohlbach, K., Jeske, S., Meinhardt, F., Rossi, R., Gudowius, S., Marquardt, T. Am. J. Hum. Genet. (2004) [Pubmed]
  8. Biosynthesis of Rhizobium meliloti lipooligosaccharide Nod factors: NodA is required for an N-acyltransferase activity. Atkinson, E.M., Palcic, M.M., Hindsgaul, O., Long, S.R. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  9. Site-specific labeling of cytoplasmic peptide:N-glycanase by N,N'-diacetylchitobiose-related compounds. Suzuki, T., Hara, I., Nakano, M., Zhao, G., Lennarz, W.J., Schindelin, H., Taniguchi, N., Totani, K., Matsuo, I., Ito, Y. J. Biol. Chem. (2006) [Pubmed]
  10. Glycoprotein-specific ubiquitin ligases recognize N-glycans in unfolded substrates. Yoshida, Y., Adachi, E., Fukiya, K., Iwai, K., Tanaka, K. EMBO Rep. (2005) [Pubmed]
  11. Proteolysis in the gut of mosquito larvae results in further activation of the Bacillus sphaericus toxin. Broadwell, A.H., Baumann, P. Appl. Environ. Microbiol. (1987) [Pubmed]
  12. Chitobiose phosphorylase from Vibrio proteolyticus, a member of glycosyl transferase family 36, has a clan GH-L-like (alpha/alpha)(6) barrel fold. Hidaka, M., Honda, Y., Kitaoka, M., Nirasawa, S., Hayashi, K., Wakagi, T., Shoun, H., Fushinobu, S. Structure (Camb.) (2004) [Pubmed]
  13. Oligosaccharides accumulated in the bovine beta-mannosidosis kidney. Jones, M.Z., Rathke, E.J., Gage, D.A., Costello, C.E., Murakami, K., Ohta, M., Matsuura, F. J. Inherit. Metab. Dis. (1992) [Pubmed]
  14. Infectious cycle analysis of a Borrelia burgdorferi mutant defective in transport of chitobiose, a tick cuticle component. Tilly, K., Grimm, D., Bueschel, D.M., Krum, J.G., Rosa, P. Vector Borne Zoonotic Dis. (2004) [Pubmed]
  15. Growth of hyperthermophilic archaeon Pyrococcus furiosus on chitin involves two family 18 chitinases. Gao, J., Bauer, M.W., Shockley, K.R., Pysz, M.A., Kelly, R.M. Appl. Environ. Microbiol. (2003) [Pubmed]
  16. Improving glycopeptide synthesis: a convenient protocol for the preparation of beta-glycosylamines and the synthesis of glycopeptides. Hackenberger, C.P., O'Reilly, M.K., Imperiali, B. J. Org. Chem. (2005) [Pubmed]
  17. Reverse hydrolysis reaction of chitin deacetylase and enzymatic synthesis of beta-D-GlcNAc-(1-->4)-GlcN from chitobiose. Tokuyasu, K., Ono, H., Hayashi, K., Mori, Y. Carbohydr. Res. (1999) [Pubmed]
  18. Glycoprotein metabolism in normal and beta-mannosidase-deficient cultured goat skin fibroblasts. Hancock, L.W., Jones, M.Z., Dawson, G. Biochem. J. (1986) [Pubmed]
  19. NKR-P1A protein, an activating receptor of rat natural killer cells, binds to the chitobiose core of uncompletely glycosylated N-linked glycans, and to linear chitooligomers. Bezouska, K., Sklenár, J., Dvoráková, J., Havlícek, V., Pospísil, M., Thiem, J., Kren, V. Biochem. Biophys. Res. Commun. (1997) [Pubmed]
  20. The membrane of the rough endoplasmic reticulum contains cytoplasmically exposed high affinity GTP-binding sites. Godelaine, D., Beaufay, H. Biochem. Biophys. Res. Commun. (1987) [Pubmed]
  21. The glycomes of Caenorhabditis elegans and other model organisms. Haslam, S.M., Gems, D., Morris, H.R., Dell, A. Biochem. Soc. Symp. (2002) [Pubmed]
  22. Structural basis of carbohydrate recognition by lectin II from Ulex europaeus, a protein with a promiscuous carbohydrate-binding site. Loris, R., De Greve, H., Dao-Thi, M.H., Messens, J., Imberty, A., Wyns, L. J. Mol. Biol. (2000) [Pubmed]
  23. In vitro killing of spores and hyphae of Aspergillus fumigatus and Rhizopus oryzae by rabbit neutrophil cationic peptides and bronchoalveolar macrophages. Levitz, S.M., Selsted, M.E., Ganz, T., Lehrer, R.I., Diamond, R.D. J. Infect. Dis. (1986) [Pubmed]
  24. Effect of the Met344His mutation on the conformational dynamics of bovine beta-1,4-galactosyltransferase: crystal structure of the Met344His mutant in complex with chitobiose. Ramakrishnan, B., Boeggeman, E., Qasba, P.K. Biochemistry (2004) [Pubmed]
  25. Characterization of the oligosaccharides of plasma sex hormone binding globulin from noncirrhotic alcoholic patients. Valladares, L., Erices, A., Lioi, X., Iturriaga, H. Steroids (2000) [Pubmed]
  26. A family of novel, acidic N-glycans in Bowes melanoma tissue plasminogen activator have L2/HNK-1-bearing antennae, many with sulfation of the fucosylated chitobiose core. Zamze, S., Wing, D.R., Wormald, M.R., Hunter, A.P., Dwek, R.A., Harvey, D.J. Eur. J. Biochem. (2001) [Pubmed]
  27. Structural basis of sugar-recognizing ubiquitin ligase. Mizushima, T., Hirao, T., Yoshida, Y., Lee, S.J., Chiba, T., Iwai, K., Yamaguchi, Y., Kato, K., Tsukihara, T., Tanaka, K. Nat. Struct. Mol. Biol. (2004) [Pubmed]
  28. A unique chitinase with dual active sites and triple substrate binding sites from the hyperthermophilic archaeon Pyrococcus kodakaraensis KOD1. Tanaka, T., Fujiwara, S., Nishikori, S., Fukui, T., Takagi, M., Imanaka, T. Appl. Environ. Microbiol. (1999) [Pubmed]
  29. Structural energetics of protein-carbohydrate interactions: Insights derived from the study of lysozyme binding to its natural saccharide inhibitors. García-Hernández, E., Zubillaga, R.A., Chavelas-Adame, E.A., Vázquez-Contreras, E., Rojo-Domínguez, A., Costas, M. Protein Sci. (2003) [Pubmed]
  30. Effect of chitobiose and chitotriose on carbon tetrachloride-induced acute hepatotoxicity in rats. Chen, A.S., Taguchi, T., Sakai, K., Matahira, Y., Wang, M.W., Miwa, I. Biol. Pharm. Bull. (2005) [Pubmed]
  31. Integumental chitin synthase activity in cell-free extracts of larvae of the Australian sheep blowfly, Lucilia cuprina, and two other species of diptera. Turnbull, I.F., Howells, A.J. Aust. J. Biol. Sci. (1983) [Pubmed]
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