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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
Chemical Compound Review

AC1MIYJ4     (2S,3S,4R,5R)-4,5,6- trihydroxy-2,3...

Synonyms: 28173-52-6, 170369-06-9
 
 
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Disease relevance of mannotriose

  • It also hydrolyzes (Man)2-GlcNAc from the urine of an alpha-mannosidosis patient, 1,4-D-mannobiose and mannotriose isolated from ivory nut mannan, 4-O-beta-D-mannopyranosyl-L-rhamnose, 6-O-beta-D-mannopyranosyl-D-galactose and 4-O-beta-D-mannopyranosyl-N-acetylglucosamine [1].
  • Protection against candidiasis by an immunoglobulin G3 (IgG3) monoclonal antibody specific for the same mannotriose as an IgM protective antibody [2].
 

High impact information on mannotriose

  • Scatchard analysis indicated that there exist two binding sites for Man3 on a homodimeric form of a 105-kDa subunit [3].
  • The minimum structural requirements for inhibition of the PNGase activity were Man3 and GlcNAc2 [3].
  • The conformity of Kd with IC50 values may be taken as an evidence for inhibition of the catalytic activity by the oligosaccharides and Man3 through the occupation of the binding sites with these molecules [3].
  • Acetolysis of the oligosaccharide with a molecular weight of 1720 released the radioactivity as mannobiose and mannotriose suggesting that these oligosaccharides contain di- and trisaccharide branches linked to the main chain in 1 leads to 6 linkages [4].
  • More constant features of PLM from serotype B strains were the incorporation of greater amounts of phytosphingosine C20, a twofold reduced glycosylation of PLM and overexpression of a beta-1,2 mannotriose, the epitope of protective antibodies [5].
 

Biological context of mannotriose

  • In the mutant system, a significant reactivity in the cross reaction between the mutant antiserum and Kloeckera brevis mannan indicates that the immunodeterminant of the mutant mannan may be a structural analogue of the side-chain oligosaccharide from K. brevis, which has phosphorylated (alpha 1--3)-linked mannotriose [6].
  • Model calculation and progress-curve analysis showed that the transglycosylation rate is the fastest of all the rates in this system, 15 s-1 compared with mannohexaose and mannotetraose hydrolysis rates of 2 s-1 and mannotriose hydrolysis rate of 0.03 s-1 at 50 degrees C [7].
 

Anatomical context of mannotriose

  • Furthermore, KM+ binding to the surface of human neutrophils is inhibited by the specific sugars, d-mannose or mannotriose [8].
 

Associations of mannotriose with other chemical compounds

  • The structures of the complexes of artocarpin with mannotriose and mannopentose reported here, together with the structures of artocarpin and its complex with Me-alpha-mannose reported earlier, show that the lectin possesses a deep-seated binding site formed by three loops [9].
  • From these and other data, we postulate that the binding site of MBP-C has an extended area of interaction, probably the size of a mannotriose, while MBP-A interacts essentially with one mannose residue [10].
 

Gene context of mannotriose

  • Here, we demonstrate that replacement of residues 185-279 within the FimH pilin domain with a corresponding segment of the type 1C fimbrial adhesin FocH leads to a loss of the multivalent mannotriose-specific binding property accompanied by the acquisition of a distinct monomannose-specific (i.e. monovalent) binding capability [11].
  • Herein, different conformations of four disaccharides (beta-4-linked mannobiose, and three galactobioses, linked alpha-(1-->3), alpha-(1-->4), and beta-(1-->4)) and one trisaccharide (beta-4-linked mannotriose) were minimized using mm3 at epsilon = 80, and the difference in energy produced by changes in torsional angles was recorded [12].

References

  1. beta-Mannosidase from the mushroom Polyporus sulfureus. Wan, C.C., Muldrey, J.E., Li, S.C., Li, Y.T. J. Biol. Chem. (1976) [Pubmed]
  2. Protection against candidiasis by an immunoglobulin G3 (IgG3) monoclonal antibody specific for the same mannotriose as an IgM protective antibody. Han, Y., Riesselman, M.H., Cutler, J.E. Infect. Immun. (2000) [Pubmed]
  3. Carbohydrate-binding property of peptide: N-glycanase from mouse fibroblast L-929 cells as evaluated by inhibition and binding experiments using various oligosaccharides. Suzuki, T., Kitajima, K., Inoue, Y., Inoue, S. J. Biol. Chem. (1995) [Pubmed]
  4. Biosynthesis of lipid-linked oligosaccharides in cotton fibers. Stimulation by lipids from pig liver. Forsee, W.T., Elbein, A.D. J. Biol. Chem. (1977) [Pubmed]
  5. Candida albicans serotype B strains synthesize a serotype-specific phospholipomannan overexpressing a beta-1,2-linked mannotriose. Trinel, P.A., Delplace, F., Maes, E., Zanetta, J.P., Mille, C., Coddeville, B., Jouault, T., Strecker, G., Poulain, D. Mol. Microbiol. (2005) [Pubmed]
  6. Comparison of the mannan structure from the cell-wall mutant Candida sp. M-7002 and its wild type. II. Immunochemical properties of the mannans. Hamada, T., Nakajima, T., Matsuda, K. Eur. J. Biochem. (1981) [Pubmed]
  7. Kinetic and stereochemical studies of manno-oligosaccharide hydrolysis catalysed by beta-mannanases from Trichoderma reesei. Harjunpää, V., Teleman, A., Siika-Aho, M., Drakenberg, T. Eur. J. Biochem. (1995) [Pubmed]
  8. Neutrophil activation induced by the lectin KM+ involves binding to CXCR2. Pereira-da-Silva, G., Moreno, A.N., Marques, F., Oliver, C., Célia Jamur, M., Panunto-Castelo, A., Roque-Barreira, M.C. Biochim. Biophys. Acta (2006) [Pubmed]
  9. Structural basis for the carbohydrate specificities of artocarpin: variation in the length of a loop as a strategy for generating ligand specificity. Jeyaprakash, A.A., Srivastav, A., Surolia, A., Vijayan, M. J. Mol. Biol. (2004) [Pubmed]
  10. Difference in binding-site architecture of the serum-type and liver-type mannose-binding proteins. Lee, R.T., Lee, Y.C. Glycoconj. J. (1997) [Pubmed]
  11. Valency conversion in the type 1 fimbrial adhesin of Escherichia coli. Sokurenko, E.V., Schembri, M.A., Trintchina, E., Kjaergaard, K., Hasty, D.L., Klemm, P. Mol. Microbiol. (2001) [Pubmed]
  12. Additive effects in the modeling of oligosaccharides with mm3 at high dielectric constants: an approach to the 'multiple minimum problem'. Stortz, C.A. Carbohydr. Res. (2006) [Pubmed]
 
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