Discovery of a single monooxygenase catalyzing the carbamate formation and ring contraction in the biosynthesis of legonmycins

Sheng Huang, Jioji Tabudravu, Somayah Sameer Elsayed, Jeanne Travert, Doe Peace, Ming Him Tong, Kwaku Kyeremeh, Sharon Kelly, Laurent Alain Claude Trembleau, Rainer Peter Ebel, Marcel Jaspars, Yi Yu (Corresponding Author), Hai Deng (Corresponding Author)

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Abstract

Pyrrolizidine alkaloids (PAs) are a group of natural products with important biological activities. Herein we report the discovery and characterization of the multifunctional FAD-dependent enzyme LgnC that was biochemically characterized in vitro to convert indolizidine intermediate into pyrrolizidine through an unusual ring expansion/contraction strategy tailoring the biosynthesis of new bacterial PAs, the legonmycins. We also confirmed that the legonmycins originate from non-ribosomal peptide synthetases (NRPS) via genomic-driven analysis, heterologous expression and gene inactivation. This is the first report to disclose the biosynthetic origin of bacterial PAs.
Original languageEnglish
Pages (from-to)12697-12701
Number of pages4
JournalAngewandte Chemie International Edition
Volume54
Issue number43
Early online date17 Jul 2015
DOIs
Publication statusPublished - 19 Oct 2015

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Keywords

  • biosynthesis
  • legonmycins
  • multifunctional enzymes
  • non-ribosomal peptide synthetases
  • pyrrolizidine alkaloids

ASJC Scopus subject areas

  • Organic Chemistry

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