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

被引：191

作者：

Barry, Sarah M. ^{[1
]}

Kers, Johan A. ^{[2
]}

Johnson, Evan G. ^{[2
]}

Song, Lijiang ^{[1
]}

Aston, Philip R. ^{[1
]}

Patel, Bhumit ^{[3
]}

Krasnoff, Stuart B. ^{[4
]}

Crane, Brian R. ^{[3
]}

Gibson, Donna M. ^{[4
]}

Loria, Rosemary ^{[2
]}

Challis, Gregory L. ^{[1
]}

机构：

[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England

[2] Cornell Univ, Dept Plant Pathol & Plant Microbe Biol, Ithaca, NY USA

[3] Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY USA

[4] USDA ARS, Robert W Holley Ctr Agr & Hlth, Ithaca, NY 14853 USA

来源：

NATURE CHEMICAL BIOLOGY | 2012年 / 8卷 / 10期

基金：

美国农业部; 英国生物技术与生命科学研究理事会;

关键词：

NITRIC-OXIDE SYNTHASE; REGIOSELECTIVE NITRATION; STREPTOMYCES; SYNTHETASE; SUBSTRATE; PROTEINS; BINDING;

D O I：

10.1038/nchembio.1048

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

070307 [化学生物学]; 071010 [生物化学与分子生物学];

摘要：

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.

引用

页码：814 / 816

页数：3

共 19 条

[1]

COMPUTER-ASSISTED IDENTIFICATION AND CLASSIFICATION OF STREPTOMYCETE PROMOTERS [J].

BOURN, WR ;

BABB, B .

NUCLEIC ACIDS RESEARCH, 1995, 23 (18) :3696-3703

[2]

Regioselective nitration of tryptophan by a complex between bacterial nitric-oxide synthase and tryptophanyl-tRNA synthetase [J].

Buddha, MR ;

Tao, T ;

Parry, RJ ;

Crane, BR .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2004, 279 (48) :49567-49570

[3]

Structure and chemistry of cytochrome P450 [J].

Denisov, IG ;

Makris, TM ;

Sligar, SG ;

Schlichting, I .

CHEMICAL REVIEWS, 2005, 105 (06) :2253-2277

[4]

Substrate binding favors enhanced NO binding to P450cam [J].

Franke, A ;

Stochel, G ;

Jung, C ;

van Eldik, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4181-4191

[5]

Quantification of nitrated tryptophan in proteins and tissues by high-performance liquid chromatography with electrospray ionization tandem mass spectrometry [J].

Ishii, Yuji ;

Ogara, Atsushi ;

Katsumata, Tsunenobu ;

Umemura, Takashi ;

Nishikawa, Akiyoshi ;

Iwasaki, Yusuke ;

Ito, Rie ;

Saito, Koichi ;

Hirose, Masao ;

Nakazawa, Hiroyuki .

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2007, 44 (01) :150-159

[6]

4-Nitrotryptophan is a substrate for the non-ribosomal peptide synthetase TxtB in the thaxtomin A biosynthetic pathway [J].

Johnson, Evan G. ;

Krasnoff, Stuart B. ;

Bignell, Dawn R. D. ;

Chung, Wen-Chuan ;

Tao, Tao ;

Parry, Ronald J. ;

Loria, Rosemary ;

Gibson, Donna M. .

MOLECULAR MICROBIOLOGY, 2009, 73 (03) :409-418

[7]

A large, mobile pathogenicity island confers plant pathogenicity on Streptomyces species [J].

Kers, JA ;

Cameron, KD ;

Joshi, MV ;

Bukhalid, RA ;

Morello, JE ;

Wach, MJ ;

Gibson, DM ;

Loria, R .

MOLECULAR MICROBIOLOGY, 2005, 55 (04) :1025-1033

[8]

Nitration of a peptide phytotoxin by bacterial nitric oxide synthase [J].

Kers, JA ;

Wach, MJ ;

Krasnoff, SB ;

Widom, J ;

Cameron, KD ;

Bukhalid, RA ;

Gibson, DM ;

Crane, BR ;

Loria, R .

NATURE, 2004, 429 (6987) :79-82

[9]

NAKAHARA K, 1993, J BIOL CHEM, V268, P8350

[10]

OMURA T, 1964, J BIOL CHEM, V239, P2379

← 1 2 →