Deciphering Pyrrolidine and Olefin Formation Mechanism in Kainic Acid Biosynthesis

Tzu Yu Chen, Shan Xue, Wei Chih Tsai, Tun Cheng Chien*, Yisong Guo*, Wei Chen Chang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)


Metalloenzyme-catalyzed cyclization involving C-H bond activation is a powerful strategy to construct molecular complexity found in natural product biosynthesis. In the isodomoic acid and kainic acid biosynthetic pathways, mononuclear non-heme iron enzymes catalyze cyclization along with desaturation reactions that install the pyrrolidine and the olefin. Using complementary approaches, a plausible reaction pathway of kainic acid formation is established. Following H atom abstraction by an Fe(IV)-oxo species, the resulting radical interacts with the N-prenyl group to promote pyrrolidine installation. The reaction then undergoes a carbocation-triggered desaturation to construct kainic acid.

Original languageEnglish
Pages (from-to)278-282
Number of pages5
JournalACS Catalysis
Issue number1
Publication statusPublished - 2021 Jan 1


  • C-H activation
  • cyclization
  • desaturation
  • enzyme mechanism
  • metalloenzyme

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry


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