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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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
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author 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.
author_facet 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.
author_sort Barry, Sarah M.
collection PubMed
description 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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spelling pubmed-35225712013-04-01 Cytochrome P450-catalysed L-tryptophan nitration in thaxtomin phytotoxin biosynthesis 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. Nat Chem Biol Article 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). 2012-10 /pmc/articles/PMC3522571/ /pubmed/22941045 http://dx.doi.org/10.1038/nchembio.1048 Text en Users may view, print, copy, download and text and data- mine the content in such documents, for the purposes of academic research, subject always to the full Conditions of use: http://www.nature.com/authors/editorial_policies/license.html#terms
spellingShingle Article
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.
Cytochrome P450-catalysed L-tryptophan nitration in thaxtomin phytotoxin biosynthesis
title Cytochrome P450-catalysed L-tryptophan nitration in thaxtomin phytotoxin biosynthesis
title_full Cytochrome P450-catalysed L-tryptophan nitration in thaxtomin phytotoxin biosynthesis
title_fullStr Cytochrome P450-catalysed L-tryptophan nitration in thaxtomin phytotoxin biosynthesis
title_full_unstemmed Cytochrome P450-catalysed L-tryptophan nitration in thaxtomin phytotoxin biosynthesis
title_short Cytochrome P450-catalysed L-tryptophan nitration in thaxtomin phytotoxin biosynthesis
title_sort cytochrome p450-catalysed l-tryptophan nitration in thaxtomin phytotoxin biosynthesis
topic Article
url 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
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