Synthesis of a novel class of glycocluster with a cyclic α-(1→6)-octaglucoside as a scaffold and their binding abilities to concanavalin A.
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.
Yang
Li-Ying
LY
Department of Life Science, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, J2-10, 4259 Nagatsutacho, Midoriku, Yokohama 226-8501, Japan.
Haraguchi
Tsuyoshi
T
Inazawa
Tomoka
T
Kajiwara
Susumu
S
Yuasa
Hideya
H
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
D005960:Glucosides; D006001:Glycoconjugates; D037102:Lectins; D010504:Periodic Acid; D003208:Concanavalin A; C009288:metaperiodate