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

薬学研究科・分子薬科学専攻

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
巻	12
号	17
DOI	https://doi.org/10.1021/ol101449x
出版ステータス	Published - 2010 9 3

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

文献へのアクセス

10.1021/ol101449x

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引用スタイル

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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

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