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Chemical Compound Review

AG-F-20184     (2R,3S,4R,5R)-2,4,5,6- tetrahydroxy-3-[(2S...

Synonyms: AC1L3UFA, ZINC31392968, Laminaribiose (mixed anomers), 0B3AA375-FC0D-41E0-8189-59C2ED91FA5C
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Disease relevance of laminaribiose


High impact information on laminaribiose

  • Crystal structures of CsCBM6-3 in complex with xylotriose, cellobiose, and laminaribiose, 2.0 A, 1.35 A, and 1.0 A resolution, respectively, reveal that the binding site of CsCBM6-3 resides on the same polypeptide face as for MvX56 and AAA [2].
  • Although laminaribiose gave strong inhibition of conidial binding to monocytes, cellobiose and oligosaccharides with beta 1,4-linked glucose residues were more potent as specific inhibitors of this binding over similar concentrations [3].
  • The enzyme had a specificity for cellobiose, requiring Pi and Mg2+ for phosphorylation, but not for cellodextrin, gentibiose, laminaribiose, lactose, maltose, kojibiose and sucrose [4].
  • The binding of banana lectin (BanLec) to laminaribiose (Glcbeta1,3Glc) and a series of novel synthetic analogues was measured by titration calorimetry to assess the contribution of the hydroxyl groups of the reducing glycosyl moiety and its 3-O-beta-substituent to binding [5].
  • Phylogeny of Alariaceae, Laminariaceae, and Lessoniaceae (Phaeophyceae) based on plastid-encoded RuBisCo spacer and nuclear-encoded ITS sequence comparisons [6].

Biological context of laminaribiose


Anatomical context of laminaribiose

  • This is consistent with in vitro findings that laminaribiose is a by-product of a newly identified glucosyltransferase (R. P. Hartland, G. W. Emerson & P. A. Sullivan, 1991, Proc R Soc Lond B 246, 155-160) associated with fungal cell walls [10].

Associations of laminaribiose with other chemical compounds


Analytical, diagnostic and therapeutic context of laminaribiose


  1. Analysis of rice glycosyl hydrolase family 1 and expression of Os4bglu12 beta-glucosidase. Opassiri, R., Pomthong, B., Onkoksoong, T., Akiyama, T., Esen, A., Ketudat Cairns, J.R. BMC Plant Biol. (2006) [Pubmed]
  2. Structure and ligand binding of carbohydrate-binding module CsCBM6-3 reveals similarities with fucose-specific lectins and "galactose-binding" domains. Boraston, A.B., Notenboom, V., Warren, R.A., Kilburn, D.G., Rose, D.R., Davies, G. J. Mol. Biol. (2003) [Pubmed]
  3. Beta 1,4-oligoglucosides inhibit the binding of Aspergillus fumigatus conidia to human monocytes. Kan, V.L., Bennett, J.E. J. Infect. Dis. (1991) [Pubmed]
  4. Purification and properties of Cellvibrio gilvus cellobiose phosphorylase. Sasaki, T., Tanaka, T., Nakagawa, S., Kainuma, K. Biochem. J. (1983) [Pubmed]
  5. Banana lectin is unique in its recognition of the reducing unit of 3-O-beta-glucosyl/mannosyl disaccharides: a calorimetric study. Winter, H.C., Oscarson, S., Slättegård, R., Tian, M., Goldstein, I.J. Glycobiology (2005) [Pubmed]
  6. Phylogeny of Alariaceae, Laminariaceae, and Lessoniaceae (Phaeophyceae) based on plastid-encoded RuBisCo spacer and nuclear-encoded ITS sequence comparisons. Yoon, H.S., Lee, J.Y., Boo, S.M., Bhattacharya, D. Mol. Phylogenet. Evol. (2001) [Pubmed]
  7. Construction and characterization of chimeric enzymes of kojibiose phosphorylase and trehalose phosphorylase from Thermoanaerobacter brockii. Yamamoto, T., Yamashita, H., Mukai, K., Watanabe, H., Kubota, M., Chaen, H., Fukuda, S. Carbohydr. Res. (2006) [Pubmed]
  8. Kinetics of substrate transglycosylation by glycoside hydrolase family 3 glucan (1-->3)-beta-glucosidase from the white-rot fungus Phanerochaete chrysosporium. Kawai, R., Igarashi, K., Kitaoka, M., Ishii, T., Samejima, M. Carbohydr. Res. (2004) [Pubmed]
  9. Reaggregation and binding of cell wall proteins from Candida albicans to structural polysaccharides. Aguado, C., Ruíz-Herrera, J., Iranzo, M., Sentandreu, R., Mormeneo, S. Res. Microbiol. (1998) [Pubmed]
  10. Synthesis of yeast cell wall glucan and evidence for glucan metabolism in a Saccharomyces cerevisiae whole cell system. Coen, M.L., Lerner, C.G., Capobianco, J.O., Goldman, R.C. Microbiology (Reading, Engl.) (1994) [Pubmed]
  11. Vanadium haloperoxidases from brown algae of the Laminariaceae family. Almeida, M., Filipe, S., Humanes, M., Maia, M.F., Melo, R., Severino, N., da Silva, J.A., Fraústo da Silva, J.J., Wever, R. Phytochemistry (2001) [Pubmed]
  12. Biophysical evidence of lipid and carbohydrate binding activities of shrimp high density lipoprotein/beta glucan binding protein. Vargas-Requena, C.L., Hernández-Santoyo, A., Yepiz-Plascencia, G., Vargas-Albores, F., Higuera-Ciapara, I., Rodríguez-Romero, A., Soulages, J.L., Sotelo-Mundo, R.R. Protein Pept. Lett. (2002) [Pubmed]
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