title: Synthesis of a novel class of glycocluster with a cyclic α-(1→6)-octaglucoside as a scaffold and their binding abilities to concanavalin A.
abstract: The synthesis of small glycoclusters with high affinity toward lectins is one of the important subjects in glycotechnology. Although cyclic α-(1→6)-d-octaglucoside (CI8) is an attractive scaffold on which to put glycosyl pendants, the compound has only secondary hydroxyl groups, which are relatively unreactive for substitution reactions. The oxidation of the vicinal diols of CI8 and reductive amination of the resultant dialdehydes with 2-aminoethyl mannoside gave mannose-CI8 conjugates with a variety of average mannose incorporation numbers (2-7). The average numbers were deduced from MALDI-TOF mass and (1)H NMR spectroscopy. The binding ability of mannose-CI8 conjugates to concanavalin A increased with the increasing numbers of average mannose incorporation, reaching a plateau at tetravalence, as estimated from a latex bead-based agglutination lectin assay. Toxicity tests demonstrated the biocompatibility of mannose-CI8 conjugates.
authors.affiliation: Department of Life Science, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, J2-10, 4259 Nagatsutacho, Midoriku, Yokohama 226-8501, Japan.
authors.forename: Li-Ying
authors.initials: LY
authors.lastname: Yang
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Haraguchi
authors.forename: Tomoka
authors.initials: T
authors.lastname: Inazawa
authors.forename: Susumu
authors.initials: S
authors.lastname: Kajiwara
authors.forename: Hideya
authors.initials: H
authors.lastname: Yuasa
mesh_terms: D003208:Concanavalin A / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry*; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D037102:Lectins / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010504:Periodic Acid / Q000737:chemistry
chemical_list: D005960:Glucosides; D006001:Glycoconjugates; D037102:Lectins; D010504:Periodic Acid; D003208:Concanavalin A; C009288:metaperiodate