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

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)1075-1082
Number of pages8
JournalBulletin of the Chemical Society of Japan
Volume95
Issue number7
DOIs
Publication statusPublished - 2022 Jul

Keywords

  • Boron-mediated aglycon delivery
  • Chemical probes
  • Late-stage glycosylation

ASJC Scopus subject areas

  • Chemistry(all)

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