Total Synthesis-Assisted Structure Determination and Biological Evaluation of Cytotoxic Cyclodepsipeptide Destruxin F.

Authors

Daiki Shirai, Shione Kojima, Hideo Kigoshi, Masahito Yoshida

Published in

Chemical & pharmaceutical bulletin. Volume 74. Issue 9. Pages 665-669.

Abstract

The structure determination of destruxin F was achieved by total synthesis. Four isomers of the α,γ-dihydroxycarboxylic acid derivatives were comprehensively prepared from chiral glycidols in an asymmetric manner, enabling the successful synthesis of all structural candidates of destruxin F. The spectral data of the (1αR,1γR)-isomer were in good agreement with those of natural destruxin F, leading to the determination of the absolute configuration of the undetermined chiral centers as 1αR and 1γR, respectively. Furthermore, biological evaluation of the synthetic compounds revealed that the proper conformation of the cyclic peptide scaffold is required to exhibit the cytotoxicity and that the structure of α-hydroxycarboxylic acid moiety regulates the potency of biological activity.

PMID:
42702558
Bibliographic data and abstract were imported from PubMed on 07 Sep 2026.

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