Solid-phase total synthesis of the chitinase inhibitor argadin using a supported acetal resin

Toshiaki Sunazuka, Akihiro Sugawara, Yoshihiko Noguchi, Toshiaki Tanaka, Kanami Iguchi, Tsuyoshi Yamamoto, Hiroaki Gouda, Kazuro Shiomi, Satoshi Õmura

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

A versatile solid-phase total synthesis was applied to the rapid preparation of Argadin, a natural product isolated and characterized as a cyclopentapeptide by our group, which possesses superior inhibitory activity against family-18 chitinases. The synthetic strategy includes peptide synthesis by using an Fmoc (9-fluorenylmethoxycarbonyl) protective group, macrolactamization, acetylguanylation and formation of hemiaminal accompanied by total deprotection, including cleavage from resin.

Original languageEnglish
Pages (from-to)495-500
Number of pages6
JournalJournal of Antibiotics
Volume62
Issue number9
DOIs
Publication statusPublished - 2009 Sep
Externally publishedYes

Keywords

  • Argadin
  • Chitinase
  • Solid phase
  • Total synthesis

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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