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

doi:10.1021/ol101449x

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

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

24 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 language	English
Pages (from-to)	3792-3795
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	17
DOIs	https://doi.org/10.1021/ol101449x
Publication status	Published - 2010 Sept 3

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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.",

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T1 - Synthesis, structure determination, and biological evaluation of destruxin e

AU - Yoshida, Masahito

AU - Takeuchi, Hisayuki

AU - Ishida, Yoshitaka

AU - Yashiroda, Yoko

AU - Yoshida, Minoru

AU - Takagi, Motoki

AU - Shin-Ya, Kazuo

AU - Doi, Takayuki

PY - 2010/9/3

Y1 - 2010/9/3

N2 - 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.

AB - 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.

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Synthesis, structure determination, and biological evaluation of destruxin e

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