title: Cytochrome P450–catalyzed L-tryptophan nitration in thaxtomin phytotoxin biosynthesis.
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).
authors.affiliation: Department of Chemistry, University of Warwick, Coventry, UK.
authors.forename: Sarah M
authors.initials: SM
authors.lastname: Barry
authors.forename: Johan A
authors.initials: JA
authors.lastname: Kers
authors.forename: Evan G
authors.initials: EG
authors.lastname: Johnson
authors.forename: Lijiang
authors.initials: L
authors.lastname: Song
authors.forename: Philip R
authors.initials: PR
authors.lastname: Aston
authors.forename: Bhumit
authors.initials: B
authors.lastname: Patel
authors.forename: Stuart B
authors.initials: SB
authors.lastname: Krasnoff
authors.forename: Brian R
authors.initials: BR
authors.lastname: Crane
authors.forename: Donna M
authors.initials: DM
authors.lastname: Gibson
authors.forename: Rosemary
authors.initials: R
authors.lastname: Loria
authors.forename: Gregory L
authors.initials: GL
authors.lastname: Challis
mesh_terms: D055162:Biocatalysis; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism*; D007211:Indoles / Q000378:metabolism*; D009569:Nitric Oxide / Q000378:metabolism*; D010879:Piperazines / Q000378:metabolism*; D010944:Plants / Q000382:microbiology*; D013302:Streptomyces / Q000378:metabolism*; D014364:Tryptophan / Q000378:metabolism*
chemical_list: D007211:Indoles; D010879:Piperazines; C406691:thaxtomine A; C406702:thaxtomine B; D009569:Nitric Oxide; D014364:Tryptophan; D003577:Cytochrome P-450 Enzyme System