Synthesis, structure determination, and biological evaluation of destruxin e

Masahito Yoshida, Hisayuki Takeuchi, Yoshitaka Ishida, Yoko Yashiroda, Minoru Yoshida, Motoki Takagi, Kazuo Shin-Ya, Takayuki Doi

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

The total synthesis of destruxin E (1) has been achieved for the first time, and the stereochemistry of its chiral center at the epoxide has been determined to be (S). The cyclization precursor 3a was synthesized by solid-phase peptide synthesis. Macrolactonization of 3a utilizing MNBA-DMAPO, followed by formation of the epoxide, then furnished destruxin E. Its diastereomer, epi-destruxin E (2), was also synthesized in the same manner. Furthermore, the biological evaluation indicated that destruxin E exhibits V-ATPase inhibitory activity 10-fold greater than that of epi-destruxin E.

Original languageEnglish
Pages (from-to)3792-3795
Number of pages4
JournalOrganic letters
Volume12
Issue number17
DOIs
Publication statusPublished - 2010 Sep 3

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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