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Nat Chem Biol. 2012 Oct;8(10):814-6.

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

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1
Department of Chemistry, University of Warwick, Coventry, UK.

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).

PMID:
22941045
PMCID:
PMC3522571
DOI:
10.1038/nchembio.1048
[Indexed for MEDLINE]
Free PMC Article
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