Design and synthesis of 24-fluorinated bafilomycin analogue as an NMR probe with potent inhibitory activity to vacuolar-type ATPase

Hajime Shibata, Hiroshi Tsuchikawa, Nobuaki Matsumori, Michio Murata, Takeo Usui

Research output: Contribution to journalArticle

4 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)474-476
Number of pages3
JournalChemistry Letters
Volume43
Issue number4
DOIs
Publication statusPublished - Jan 1 2014
Externally publishedYes

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Vacuolar Proton-Translocating ATPases
Molecular Probes
Fluorine
Biological Products
Adenosine Triphosphatases
Nuclear magnetic resonance
3-hydroxybutanal

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Design and synthesis of 24-fluorinated bafilomycin analogue as an NMR probe with potent inhibitory activity to vacuolar-type ATPase. / Shibata, Hajime; Tsuchikawa, Hiroshi; Matsumori, Nobuaki; Murata, Michio; Usui, Takeo.

In: Chemistry Letters, Vol. 43, No. 4, 01.01.2014, p. 474-476.

Research output: Contribution to journalArticle

Shibata, Hajime ; Tsuchikawa, Hiroshi ; Matsumori, Nobuaki ; Murata, Michio ; Usui, Takeo. / Design and synthesis of 24-fluorinated bafilomycin analogue as an NMR probe with potent inhibitory activity to vacuolar-type ATPase. In: Chemistry Letters. 2014 ; Vol. 43, No. 4. pp. 474-476.
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