Parallel Synthesis and Biological Evaluation of Destruxin E Analogs Modified with a Side Chain in the α-Hydroxycarboxylic Acid Moiety

Masahito Yoshida, Kenta Adachi, Hayato Murase, Hiroshi Nakagawa, Takayuki Doi

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

This study demonstrates the synthesis and biological evaluation of destruxin E analogs possessing various functional groups in the α-hydroxycarboxylic acid moiety. Parallel synthesis of eleven analogs was successfully achieved through solution-phase peptide synthesis and macrolactonization. Biological evaluation of the synthetic analogs using osteoclast-like multi nuclear cells (OCLs) revealed that the epoxide group in the side chain of α-hydroxycarboxylic acid and the orientation of the oxygen atom are essential factors in the desired potent activity that induces morphological changes in OCLs for the inhibition of bone-resorbing activity.

Original languageEnglish
Pages (from-to)1669-1676
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number7
DOIs
Publication statusPublished - 2019 Feb 21

Keywords

  • Cyclodepsipeptide
  • Natural products
  • Osteoclasts
  • Total synthesis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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