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

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 synt...

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Detalles Bibliográficos
Autores principales: Barry, Sarah M., Kers, Johan A., Johnson, Evan G., Song, Lijiang, Aston, Philip R., Patel, Bhumit, Krasnoff, Stuart B., Crane, Brian R., Gibson, Donna M., Loria, Rosemary, Challis, Gregory L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2012
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3522571/
https://www.ncbi.nlm.nih.gov/pubmed/22941045
http://dx.doi.org/10.1038/nchembio.1048
Descripción
Sumario: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 non-proteinogenic 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).

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