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

研究成果: Article査読

18 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)3792-3795
ページ数4
ジャーナルOrganic letters
12
17
DOI
出版ステータスPublished - 2010 9 3

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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