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Chemical Compound Review

CHEMBL1222017     N-[(2R,3R,4R,5S,6R)-5- [(2R,3R,4R,5S,6R)-3...

Synonyms: CHEBI:41763, CHEBI:71404, CPD-13227, AC1L9GGJ, 1at5, ...
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Disease relevance of chitotriose


High impact information on chitotriose

  • Heat-inactivated SaG as well as SaG treated with both polyclonal and monoclonal specific antibodies or enzyme inhibitors such as chitotriose or hydrolyzed peptidoglycan had no effect on lymphocyte response to mitogens [4].
  • The gene product hydrolyzes methylumbelliferyl beta-D conjugates of chitotriose, chitobiose, N-acetylglucosamine, and N-acetylgalactosamine and has, therefore, been termed a beta-N-acetylhexosaminidase [5].
  • However, the binding site of AVR4 is larger than that of Hevein, i.e. AVR4 interacts strictly with chitotriose, whereas Hevein can also interact with the monomer N-acetylglucosamine [6].
  • The absence of this domain does not affect the ability of the enzyme to hydrolyze the soluble substrate, triacetylchitotriose, but abolishes hydrolysis of insoluble chitin [7].
  • The protein binds specifically to tri-N-acetyl chitotriose and reacetylated chitosan in vitro [8].

Biological context of chitotriose


Anatomical context of chitotriose

  • Epithelial cell surfaces bound fluoresceinated pokeweed mitogen, indicating the constitutive presence of LAG-bearing molecules at the cell surface; pokeweed mitogen binding to the cell surface was completely blocked by 10 mM chitotriose [13].
  • The 220-kDa protein agglutinates human erythrocytes, and agglutination is inhibited by micromolar concentrations of hyaluronic acid, chitin, chitin-derived products (chitotriose), and antibodies to the purified protein [14].
  • All interactions were specifically inhibited by low concentrations of chitotriose (GlcNAcbeta1 leads to 4GlcNAcbeta1 leads to 4GlcNAc) and the bacterial cell wall tetrasaccharide, GlcNAcbeta1 leads to 4MurNAcbeta1 leads to 4GlcNAcbeta1 leads to 4MurNAc [15].
  • In a 4 h biological assay concentration dependent partial inhibition of neurite growth on laminin was observed in the presence of (i) alpha-lactalbumin, a specific inhibitor of the enzyme, (ii) N-acetylglucosamine (GlcNac), the appropriate acceptor substrate, or its polymer chitotriose, and (iii) UDPgal, the catalytic substrate [16].
  • This study indicates that among various chitooligosaccharides, only chitobiose and chitotriose can be appreciably absorbed from the gastrointestinal tract [12].

Associations of chitotriose with other chemical compounds

  • These latter results suggested that the essential bactericidal property of lysozyme was its extreme cationic nature and that some bacterial endogenous activities, inhibitable by chitotriose and chitobiose, were essential for expression of the bactericidal activity of either native or muramidase-inactive lysozyme or of the cationic homopolypeptides [17].
  • Inactivation of the muramidase activity of lysozyme was achieved by reduction of essential disulfides with dithiothreitol (DTT) or by incubation with the chitin oligosaccharides chitotriose and chitobiose [17].
  • We further localize its binding site to a variant of the chitotriose structure in the tri-mannosyl core of the membrane glycoprotein [18].
  • Chitobiose and chitotriose were more potent than the 3 reference compounds in scavenging hydroxyl radicals produced by photolysis of zinc oxide: IC(50) values of the 2 oligomers were 30 and 55 microM, respectively [19].

Gene context of chitotriose


Analytical, diagnostic and therapeutic context of chitotriose


  1. Legionella pneumophila type II secretome reveals unique exoproteins and a chitinase that promotes bacterial persistence in the lung. Debroy, S., Dao, J., S??derberg, M., Rossier, O., Cianciotto, N.P. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  2. Endothelial cell GlcNAc beta 1-4GlcNAc epitopes for outer membrane protein A enhance traversal of Escherichia coli across the blood-brain barrier. Prasadarao, N.V., Wass, C.A., Kim, K.S. Infect. Immun. (1996) [Pubmed]
  3. Purification and hydrolytic action of a chitosanase from Nocardia orientalis. Sakai, K., Katsumi, R., Isobe, A., Nanjo, F. Biochim. Biophys. Acta (1991) [Pubmed]
  4. Staphylococcal endo-beta-N-acetylglucosaminidase inhibits response of human lymphocytes to mitogens and interferes with production of antibodies in mice. Valisena, S., Varaldo, P.E., Satta, G. J. Clin. Invest. (1991) [Pubmed]
  5. Sequence analysis of the beta-N-acetylhexosaminidase gene of Vibrio vulnificus: evidence for a common evolutionary origin of hexosaminidases. Somerville, C.C., Colwell, R.R. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  6. Binding of the AVR4 elicitor of Cladosporium fulvum to chitotriose units is facilitated by positive allosteric protein-protein interactions: the chitin-binding site of AVR4 represents a novel binding site on the folding scaffold shared between the invertebrate and the plant chitin-binding domain. van den Burg, H.A., Spronk, C.A., Boeren, S., Kennedy, M.A., Vissers, J.P., Vuister, G.W., de Wit, P.J., Vervoort, J. J. Biol. Chem. (2004) [Pubmed]
  7. Structural and functional definition of the human chitinase chitin-binding domain. Tjoelker, L.W., Gosting, L., Frey, S., Hunter, C.L., Trong, H.L., Steiner, B., Brammer, H., Gray, P.W. J. Biol. Chem. (2000) [Pubmed]
  8. Characterization of a major peritrophic membrane protein, peritrophin-44, from the larvae of Lucilia cuprina. cDNA and deduced amino acid sequences. Elvin, C.M., Vuocolo, T., Pearson, R.D., East, I.J., Riding, G.A., Eisemann, C.H., Tellam, R.L. J. Biol. Chem. (1996) [Pubmed]
  9. Local effects of amino acid substitutions on the active site region of lysozyme: a comparison of physical and immunological results. Hornbeck, P.V., Wilson, A.C. Biochemistry (1984) [Pubmed]
  10. 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]
  11. Heterologous rhizobial lipochitin oligosaccharides and chitin oligomers induce cortical cell divisions in red clover roots, transformed with the pea lectin gene. Díaz, C.L., Spaink, H.P., Kijne, J.W. Mol. Plant Microbe Interact. (2000) [Pubmed]
  12. Pharmacokinetics of chitobiose and chitotriose administered intravenously or orally to rats. Chen, A.S., Taguchi, T., Okamoto, H., Danjo, K., Sakai, K., Matahira, Y., Wang, M.W., Miwa, I. Biol. Pharm. Bull. (2005) [Pubmed]
  13. Lactosaminoglycan assembly, cell surface expression, and release by mouse uterine epithelial cells. Dutt, A., Carson, D.D. J. Biol. Chem. (1990) [Pubmed]
  14. Isolation of a 220-kilodalton protein with lectin properties from a virulent strain of Entamoeba histolytica. Rosales-Encina, J.L., Meza, I., López-De-León, A., Talamás-Rohana, P., Rojkind, M. J. Infect. Dis. (1987) [Pubmed]
  15. Interaction of wheat-germ agglutinin with bacterial cells and cell-wall polymers. Lotan, R., Sharon, N., Mirelman, D. Eur. J. Biochem. (1975) [Pubmed]
  16. Neurite formation on laminin: effects of a galactosyltransferase on primary sensory neurons. Riopelle, R.J., Dow, K.E. Brain Res. (1991) [Pubmed]
  17. 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]
  18. Characterization of membrane N-glycan binding sites of lysozyme for cardiac depression in sepsis. Jacobs, H., Mink, S.N., Duke, K., Bose, D., Cheng, Z.Q., Howlett, S., Ferrier, G.R., Light, R.B. Intensive care medicine. (2005) [Pubmed]
  19. Antioxidant activities of chitobiose and chitotriose. Chen, A.S., Taguchi, T., Sakai, K., Kikuchi, K., Wang, M.W., Miwa, I. Biol. Pharm. Bull. (2003) [Pubmed]
  20. Oligosaccharide preferences of beta1,4-galactosyltransferase-I: crystal structures of Met340His mutant of human beta1,4-galactosyltransferase-I with a pentasaccharide and trisaccharides of the N-glycan moiety. Ramasamy, V., Ramakrishnan, B., Boeggeman, E., Ratner, D.M., Seeberger, P.H., Qasba, P.K. J. Mol. Biol. (2005) [Pubmed]
  21. Characterization of covalently cross-linked pancreatic somatostatin receptors. Susini, C., Bailey, A., Szecowka, J., Williams, J.A. J. Biol. Chem. (1986) [Pubmed]
  22. Solution- and bound-state conformational study of N,N',N"-triacetyl chitotriose and other analogous potential inhibitors of hevamine: application of trNOESY and STD NMR spectroscopy. Germer, A., Mügge, C., Peter, M.G., Rottmann, A., Kleinpeter, E. Chemistry (Weinheim an der Bergstrasse, Germany) (2003) [Pubmed]
  23. Stereochemical course of the hydrolysis reaction catalyzed by chitinases A1 and D from Bacillus circulans WL-12. Armand, S., Tomita, H., Heyraud, A., Gey, C., Watanabe, T., Henrissat, B. FEBS Lett. (1994) [Pubmed]
  24. Lectin-mediated bioadhesion: preparation, stability and caco-2 binding of wheat germ agglutinin-functionalized Poly(D,L-lactic-co-glycolic acid)-microspheres. Ertl, B., Heigl, F., Wirth, M., Gabor, F. Journal of drug targeting. (2000) [Pubmed]
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