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

doi:10.1246/cl.131099

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 journal › Article › peer-review

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 language	English
Pages (from-to)	474-476
Number of pages	3
Journal	Chemistry Letters
Volume	43
Issue number	4
DOIs	https://doi.org/10.1246/cl.131099
Publication status	Published - 2014
Externally published	Yes

All Science Journal Classification (ASJC) codes

Chemistry(all)

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10.1246/cl.131099

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AU - Shibata, Hajime

AU - Tsuchikawa, Hiroshi

AU - Matsumori, Nobuaki

AU - Murata, Michio

AU - Usui, Takeo

PY - 2014

Y1 - 2014

N2 - 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.

AB - 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.

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

Abstract

All Science Journal Classification (ASJC) codes

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