4.6 Article

Sugar-Decorated Sugar Vesicles: Lectin-Carbohydrate Recognition at the Surface of Cyclodextrin Vesicles

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 16, 期 9, 页码 2790-2796

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200902423

关键词

cyclodextrins; lectins; molecular recognition; self-assembly; vesicles

资金

  1. Deutsche Forschungsgemeinschaft [Ra 1732/1-1]

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An artificial glycocalix self-assembles when unilamellar bilayer vesicles of amphiphilic beta-cyclodextrins are decorated with maltose and lactose by host-guest interactions. To this end, maltose and lactose were conjugated with adamantane through a tetra(ethyleneglycol) spacer. Both carbohydrate-adamantane conjugates strongly bind to beta-cyclodextrin (K-a approximate to 4 x 10(4) M-1). The maltose-decorated vesicles readily agglutinate (aggregate) in the presence of the lectin concanavalin A, whereas the lactose-decorated vesicles agglutinate in the presence of peanut agglutinin. The orthogonal multivalent interaction in the ternary system of host vesicles, guest carbohydrates, and lectins was investigated by using isothermal titration calorimetry, dynamic light scattering, UV/Vis spectroscopy, and cryogenic transmission electron microscopy. It was shown that agglutination is reversible, and the noncovalent interaction can be suppressed and eliminated by the addition of competitive inhibitors, such as D-glucose or beta-cyclodextrin. Also, it was shown that agglutination depends on the surface coverage of carbohydrates on the vesicles.

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