Accelerated <i>O</i>-Glycosylation under Frozen Conditions and Its Application to the Synthesis of Complex Glycans

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  • Ishiwata Akihiro
    RIKEN Advanced Science Institute, 2-1, Hirosawa, Wako, Saitama 351-0198, Japan
  • Sakurai Ayaka
    RIKEN Advanced Science Institute, 2-1, Hirosawa, Wako, Saitama 351-0198, Japan
  • Ito Yukishige
    RIKEN Advanced Science Institute, 2-1, Hirosawa, Wako, Saitama 351-0198, Japan ERATO Ito Glycotrilogy Project, JST, 2-1, Hirosawa, Wako, Saitama 351-0198, Japan

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  • 凍結反応条件下における<i>O</i>- グリコシル化反応の加速と複雑な糖鎖の合成への応用
  • Accelerated O-Glycosylation under Frozen Conditions and Its Application to the Synthesis of Complex Glycans

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Abstract

Enormous rate acceleration was observed when O-glycosylation was conducted in p-xylene below its freezing point, as determined by comparative studies under both frozen and unfrozen conditions. The mechanistic implications of stereoselectivity on glycosylation under frozen systems were also investigated. Examination of the effects of various factors, such as solvent, concentration, anomeric configuration and protective groups of the donor, revealed that the stereoselectivity was affected by concentration both in liquid and in frozen conditions. The rate acceleration in frozen solvent was caused by the highly concentrated environments found therein. The substrate concentration under frozen conditions was estimated to be about 50 times higher than that before freezing. This manuscript also summarizes the application of this technique to the synthesis of complex glycans as well as bioactive molecules.

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