Reaction Mechanism of a Nonheme Iron Enzyme Catalyzed Oxidative Cyclization via C-C Bond Formation

Wei Chen Chang, Zhi Jie Yang, Yueh Hua Tu, Tun Cheng Chien

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

A complementary study including design of mechanistic probes, biochemical assays, model analysis, and liquid chromatography coupled mass spectrometry was conducted to establish the reaction mechanism for a nonheme iron enzyme catalyzed (?)-podophyllotoxin formation. Our results indicate that the originally proposed hydroxylated intermediate is unlikely to be involved in this reaction. Instead, the formation of benzylic radical/carbocation intermediate can be utilized to trigger the C-C bond formation to construct the C-ring of (?)-podophyllotoxin.

Original languageEnglish
Pages (from-to)228-232
Number of pages5
JournalOrganic Letters
Volume21
Issue number1
DOIs
Publication statusPublished - 2019 Jan 4

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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