Synthesis of a set of di- and tri-sulfated galabioses

Tomoaki Yoshida, Taku Chiba, Takashi Yokochi, Kikuo Onozaki, Tsuyoshi Sugiyama, Izumi Nakashima

研究成果: Article査読

7 被引用数 (Scopus)

抄録

Among cell-adhesion molecules, L-selectin recognizes sulfated sLex 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 sLex. 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 α and β 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%).

本文言語English
ページ(範囲)167-180
ページ数14
ジャーナルCarbohydrate Research
335
3
DOI
出版ステータスPublished - 08-10-2001
外部発表はい

All Science Journal Classification (ASJC) codes

  • 分析化学
  • 生化学
  • 有機化学

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