Total Biosynthesis of Brassicicenes: Identification of a Key Enzyme for Skeletal Diversification

Akihiro Tazawa, Ying Ye, Taro Ozaki, Chengwei Liu, Yasushi Ogasawara, Tohru Dairi, Yusuke Higuchi, Nobuo Kato, Katsuya Gomi, Atsushi Minami, Hideaki Oikawa

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The biosynthetic pathway of brassicicenes, derived from the phytopathogen Pseudocercospora fijiensis, was fully reconstituted. Heterologous expression of the eight genes highly expressed in infected leaf tissues generated a new brassicicene derivative as a final product. Together with the characterization of P450 from Alternaria brassicicola, a late stage of the biosynthetic pathway, which generates remarkable structural diversity, has been proposed. Notably, a unique P450 that converts 3 to the structurally distinct 4 and 6 was identified.

Original languageEnglish
Pages (from-to)6178-6182
Number of pages5
JournalOrganic letters
Volume20
Issue number19
DOIs
Publication statusPublished - 2018 Oct 5

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Tazawa, A., Ye, Y., Ozaki, T., Liu, C., Ogasawara, Y., Dairi, T., Higuchi, Y., Kato, N., Gomi, K., Minami, A., & Oikawa, H. (2018). Total Biosynthesis of Brassicicenes: Identification of a Key Enzyme for Skeletal Diversification. Organic letters, 20(19), 6178-6182. https://doi.org/10.1021/acs.orglett.8b02654