Synthesis of a set of di- and tri-sulfated galabioses |
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Authors: | Yoshida T Chiba T Yokochi T Onozaki K Sugiyama T Nakashima I |
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Affiliation: | Department of Microbiology and Immunology, Aichi Medical University, 480-1195, Aichi, Japan. tomo@aichi-med-u.ac.jp |
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Abstract: | Among cell-adhesion molecules, L-selectin recognizes sulfated sLe(x) with relatively low affinity. Here, we aimed at artificial mimics by synthesizing a set of di- and tri-sulfated galabioses, which may surpass the affinity of sulfated sLe(x). As a strategy to obtain 3',6',6-tri-O-sulfogalabioses, regioselective reductive cleavage of 4,6- and 4',6'-di-O-benzylidenegalabioses was employed. Two suitably protected galactose precursors were conjugated to yield alpha and beta anomers (48 and 18%, respectively) by using a pentenyl galactoside donor and iodinium di-sym-collidine perchlorate as the catalyst. For synthesizing the 3',6-di-O-sulfogalabiose, however, a trichloroacetimidate donor was superior (52%) to the pentenyl one (30%). |
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