Efficient Strategy for the Preparation of Chemical Probes of Biologically Active Glycosides Using a Boron-Mediated Aglycon Delivery (BMAD) Method

Kosuke Kimura, Takeshi Yasunaga, Takumi Makikawa, Daisuke Takahashi, Kazunobu Toshima

研究成果: Article査読

抄録

Development of an efficient method for the analysis and identification of the target proteins with which biologically active glycosides directly interact is highly desirable in many research fields. In this article, we report an efficient strategy for the preparation of chemical probes of biologically active glycosides using a reaction sequence of i) a boron-mediated aglycon delivery (BMAD) with an N3-functionalized 1,2-anhydroglu-cose donor, ii) deprotection, and iii) strain-promoted azidealkyne cycloaddition. Using the synthesized chemical probes, we successfully demonstrated that the target proteins of a cardiac glycoside, lanatoside C (1), can be visualized and identified in human colon cancer HCT116 cells.

本文言語English
ページ(範囲)1075-1082
ページ数8
ジャーナルBulletin of the Chemical Society of Japan
95
7
DOI
出版ステータスPublished - 2022 7月

ASJC Scopus subject areas

  • 化学 (全般)

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