Preparation and characterization of branched beta-cyclodextrins having alpha-L-fucopyranose and a study of their functions.
Three positional isomers of 6(1),6(n)-di-O-(alpha-L-fucopyranosyl)-beta-cyclodextrin [6(1),6(n)-di-O-(alpha-L-Fuc)-betaCD, n=2-4] were chemically synthesized by using the corresponding authentic compounds, 6(1),6(n)-di-O-(tert-butyldimethylsilyl)-betaCD (n=2-4) as fucosyl acceptors and 2,3,4-tri-O-benzyl-L-fucopyranosyl trichloroacetimidate as a fucosyl donor. Their structures were analyzed by HPLC, MS and NMR spectroscopy. The hemolytic activities of the alpha-L-Fuc-betaCDs were lower than that of betaCD, while the water solubility of these branched betaCDs was much higher than that of betaCD. The molecular interaction between these compounds and the fucose-binding lectin, Aleuria aurantia lectin (AAL), was investigated by using an optical biosensor based on the surface plasmon resonance (SPR) technique. The order of binding affinity, as a function of the fucose-binding position, was 6(1),6(4)- > 6(1),6(3)- > 6(1),6(2)-di-O-(alpha-L-Fuc)-betaCD > 6-O-(alpha-L-Fuc)-betaCD.
Nishi
Yuki
Y
School of Pharmaceutical Sciences, Mukogawa Women's University, Nishinomiya, Japan.
Tanimoto
Toshiko
T
D004912:Erythrocytes / Q000187:drug effects / Q000276:immunology; D005643:Fucose / Q000031:analogs & derivatives* / Q000737:chemistry*; D006461:Hemolysis / Q000187:drug effects; D006801:Humans; D007536:Isomerism; D037102:Lectins / Q000378:metabolism; D012995:Solubility; D020349:Surface Plasmon Resonance; D014867:Water / Q000737:chemistry; D047392:beta-Cyclodextrins / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism* / Q000494:pharmacology
D037102:Lectins; D047392:beta-Cyclodextrins; C064549:lectin, Aleuria aurantia; D014867:Water; D005643:Fucose; C031215:betadex