Cytochrome P450-catalyzed L-tryptophan nitration in thaxtomin phytotoxin biosynthesis

Sarah M. Barry, Johan A. Kers, Evan G. Johnson, Lijiang Song, Philip R. Aston, Bhumit Patel, Stuart B. Krasnoff, Brian R. Crane, Donna M. Gibson, Rosemary Loria, Gregory L. Challis

Research output: Contribution to journalArticleResearchpeer-review

125 Citations (Scopus)

Abstract

Thaxtomin phytotoxins produced by plant-pathogenic Streptomyces species contain a nitro group that is essential for phytotoxicity. The N,N′-dimethyldiketopiperazine core of thaxtomins is assembled from L-phenylalanine and L-4-nitrotryptophan by a nonribosomal peptide synthetase, and nitric oxide synthase-generated NO is incorporated into the nitro group, but the biosynthesis of the nonproteinogenic amino acid L-4-nitrotryptophan is unclear. Here we report that TxtE, a unique cytochrome P450, catalyzes L-tryptophan nitration using NO and O 2.

Original languageEnglish
Pages (from-to)814-816
Number of pages3
JournalNature Chemical Biology
Volume8
Issue number10
DOIs
Publication statusPublished - 2012
Externally publishedYes

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