Design and Synthesis of 24-Fluorinated Bafilomycin Analogue as an NMR Probe with Potent Inhibitory Activity to Vacuolar-type ATPase

• Shibata Hajime

  Graduate School of Science, Osaka University ERATO, Lipid Active Structure Project, Japan Science and Technology Agency

• Tsuchikawa Hiroshi

  Graduate School of Science, Osaka University

• Matsumori Nobuaki

  Graduate School of Science, Osaka University

• Murata Michio

  Graduate School of Science, Osaka University ERATO, Lipid Active Structure Project, Japan Science and Technology Agency

• Usui Takeo

  Faculty of Life and Environmental Sciences, University of Tsukuba

Abstract

A fluorine-labeled bafilomycin analogue was designed and convergently synthesized from three segments via the Stille coupling, macrolactonization, and diastereoselective aldol reaction. The V-ATPase inhibitory activity of the analogue was comparable to that of the natural product, indicating its utility as a potential molecular probe for investigating the inhibition mechanism of bafilomycin by NMR.

Journal

• Chemistry Letters

  Chemistry Letters 43 (4), 474-476, 2014

  The Chemical Society of Japan

Keywords

• General Chemistry

Details

• CRID: 1390001204588764160
• NII Article ID: 130004868062
• DOI: 10.1246/cl.131099
• COI: 1:CAS:528:DC%2BC2cXns1Glsr8%3D
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/43/4/474/55640840/cl.131099.pdf
• Text Lang: en
• Data Source:
  • JaLC
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed