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

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

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Abstract

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%).

Original languageEnglish
Pages (from-to)167-180
Number of pages14
JournalCarbohydrate Research
Volume335
Issue number3
DOIs
Publication statusPublished - 08-10-2001

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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    Yoshida, T., Chiba, T., Yokochi, T., Onozaki, K., Sugiyama, T., & Nakashima, I. (2001). Synthesis of a set of di- and tri-sulfated galabioses. Carbohydrate Research, 335(3), 167-180. https://doi.org/10.1016/S0008-6215(01)00222-1