Biosynthesis of Shearinine: Diversification of a Tandem Prenyl Moiety of Fungal Indole Diterpenes

Chengwei Liu, Atsushi Minami, Tohru Dairi, Katsuya Gomi, Barry Scott, Hideaki Oikawa

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The late-stage biosynthetic pathway of the indole diterpene shearinine involving four enzymatic reactions (JanQDOJ) was elucidated by an efficient heterologous expression system using Aspergillus oryzae. Key oxidative cyclization, forming a characteristic A/B bicyclic shearinine core by flavoprotein oxidase, was studied using a substrate analogue and a buffer containing H218O. These experimental data provided evidence that JanO catalyzes two-step oxidation via a hydroxylated product and that the JanO reaction involves the hydride-transfer mechanism.

Original languageEnglish
Pages (from-to)5026-5029
Number of pages4
JournalOrganic letters
Volume18
Issue number19
DOIs
Publication statusPublished - 2016 Oct 7

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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