Nitration of a peptide phytotoxin by bacterial nitric oxide synthase

Nature

Volumn 429, Issue 6987, 2004, Pages 79-82

  Kers, Johan A ^a   Wach, Michael J ^a   Krasnoff, Stuart U ^a   Widom, Joanne ^a   Cameron, Kimberly D ^a   Dukhalid, Raghida A ^a,c   Gibson, Donna M ^b   Crane, Brian R ^a   Loria, Rosemary ^a  

^a Department of Obstetrics Gynecology   (United States)

^b AGRICULTURAL RESEARCH SERVICE   (United States)

^c HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; BACTERIOLOGY; BIOSYNTHESIS; BLOOD; ENZYMES; GENES; HORMONES; PROTEINS;

BLOOD PRESSURE; NERVE TRANSMISSION;

NITRATION;

BACTERIAL DNA; BACTERIAL ENZYME; NITRIC OXIDE; NITRIC OXIDE SYNTHASE; PLANT TOXIN; THAXTOMIN A; UNCLASSIFIED DRUG; ARGININE; DRUG DERIVATIVE; INDOLE DERIVATIVE; N(OMEGA) HYDROXYARGININE; N(OMEGA)-HYDROXYARGININE; NITRATE; NITRITE; NITROGEN; PIPERAZINE DERIVATIVE; THAXTOMINE A; TOXIN;

BIOLOGY; MAMMAL;

ARTICLE; BACTERIAL GENE; BACTERIUM CULTURE; BIOSYNTHESIS; DNA SEQUENCE; ENZYME ACTIVITY; NITRATION; NONHUMAN; NOS GENE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOTIDE SEQUENCE; PLANT DISEASE; PLANT PATHOGEN INTERACTION; PRIORITY JOURNAL; STREPTOMYCES; TOXIN ANALYSIS; CHEMISTRY; DRUG EFFECT; ENZYMOLOGY; GENE DELETION; GENETICS; METABOLISM; MOLECULAR GENETICS; PLANT;

BACTERIA (MICROORGANISMS); MAMMALIA; POSIBACTERIA; STREPTOMYCES; STREPTOMYCES TURGIDISCABIES;

ARGININE; GENE DELETION; GENES, BACTERIAL; INDOLES; MOLECULAR SEQUENCE DATA; NITRATES; NITRIC OXIDE SYNTHASE; NITRITES; NITROGEN; PIPERAZINES; PLANTS; STREPTOMYCES; TOXINS, BIOLOGICAL;

EID: 2342621532     PISSN: 00280836     EISSN: None     Source Type: Journal    
DOI: 10.1038/nature02504     Document Type: Article

References (30)

1. Lipton, S. Physiology. Nitric oxide and respiration. Nature 413, 118-119 (2001).
2. Nathan, C. Inducible nitric oxide synthase: What difference does it make? J. Clin. Invest. 100, 2417-2423 (1997).
3. Christopherson, K. S. & Bredt, D. S. Nitric oxide in excitable tissues: Physiological roles and disease. J. Clin. Invest. 100, 2424-2429 (1997).
4. Garthwaite, J. & Boulton, C. L. Nitric-oxide signaling in the central-nervous system. Annu. Rev. Physiol. 57, 683-706 (1995).
5. Torreilles, J. Nitric oxide: one of the more conserved and widespread signaling molecules. Front. Biosci. 6, D1161-D1172 (2001).
6. Chen, Y. J. & Rosazza, J. P. N. Purification and characterization of nitric oxide synthase (NOSNoc) from a Nocardia species. J. Bacteriol. 177, 5122-5128 (1995).
7. Choi, W. S., Chang, M. S., Han, J. W., Hong, S. Y. & Lee, H. W. Identification of nitric oxide synthase in Staphylococcus aureus. Biochem. Biophys. Res. Commun. 237, 554-558 (1997).
8. Healy, F. G., Wach, M., Krasnoff, S. B., Gibson, D. M. & Loria, R. The txtAB genes of the plant pathogen Streptomyces acidiscabies encode a peptide synthetase required for phytotoxin thaxtomin A production and pathogenicity. Mol. Microbiol. 38, 794-804 (2000).
9. Adak, S. et al. Cloning, expression, and characterization of a nitric oxide synthase protein from Deinococcus radiodurans. Proc. Natl Acad. Sci. USA 99, 107-112 (2002).
10. Pant, K., Bilwes, A. M., Adak, S., Stuehr, D. J. & Crane, B. R. Structure of a nitric oxide synthase heme protein from Bacillus subtilis. Biochemistry 41, 11071-11079 (2002).
11. Adak, S., Aulak, K. & Stuehr, D. J. Evidence for nitric oxide production by a nitric-oxide synthase-like protein from Bacillus subtilis. J. Biol. Chem. 277, 16167-16171 (2002).
12. Alderton, W. K., Cooper, C. E. & Knowles, R. G. Nitric oxide synthases: structure, function and inhibition. Biochem. J. 337, 593-615 (2001).
13. Pfeiffer, S., Mayer, B. & Hemmens, B. Nitric oxide: Chemical puzzles posed by a biological messenger. Angew. Chem. Int. Edn Engl. 38, 1714-1731 (1999).
14. Stuehr, D. J. Mammalian nitric oxide synthases. Biochim. Biophys. Acta 1411, 217-230 (1999).
15. Sun, J., Kelemen, G. H., Fernandez-Abalos, J. M. & Bibb, M. J. Green fluorescent protein as a reporter for spatial and temporal gene expression in Streptomyces coelicolor A3(2). Microbiology 145, 2221-2227 (1999).
16. Southan, G. J. & Szabo, C. Selective pharmacological inhibition of distinct nitric oxide synthase isoforms. Biochem. Pharmacol. 51, 383-394 (1996).
17. Carter, G. T. et al. Direct biochemical nitration in the biosynthesis of dioxapyrrolomycin: A unique mechanism for the introduction of nitro groups in microbial products. J. Chem. Soc. Chem. Commun. 17, 1271-1273 (1989).
18. Koppenol, W. H. The basic chemistry of nitrogen monoxide and peroxynitrite. Free Radical Biol. Med. 25, 385-391 (1998).
19. Hughes, M. N. Relationships between nitric oxide, nitroxyl ion, nitrosonium cation and peroxynitrite. Biochim. Biophys. Acta 1411, 263-272 (1999).
20. Ridd, J. H. Some unconventional pathways in aromatic nitration. Acta Chem. Scand. A 52, 11-22 (1998).
21. Packer, L. E. (ed.) Nitric oxide. Part B. Physiological and pathological processes. Methods Enzymol. 268 (1996).
22. Ischiropoulos, H. (ed.) Serial review: Reactive nitrogen species, tyrosine nitration and cell signaling. Free Radical Biol. Med. 33 (2002).
23. Alvarez, B. et al. Peroxynitrite-dependent tryptophan nitration. Chem. Res. Toxicol. 9, 390-396 (1996).
24. Jalal, M. A. F., Hossain, M. B. & Van der Helm, D. Structure of anticancer antibiotic L-alanosine. Acta Crystallogr. C 42, 733-738 (1986).
25. Ohba, K. et al. Nitropeptin, a new dipeptide antibiotic possessing a nitro group. J. Antibiot. 40, 709-713 (1987).
26. Goyer, C., Vachon, J. & Beaulieu, C. Pathogenicity of Streptomyces scabies mutants altered in thaxtomin A production. Phytopathology 88, 442-445 (1998).
27. 15N heteronuclear shift correlation at natural abundance. J. Nat. Prod. 63, 543-585 (2000).
28. Kieser, T., Bibb, M. J., Buttner, M. J., Chater, K. F. & Hopwood, D. A. Practical Streptomyces Genetics (John Innes Foundation, Norwich, 2000).
29. MacNeil, D. J. et al. Analysis of Streptomyces avermitilis genes required for avermectin biosynthesis utilizing a novel integration vector. Gene 111, 61-68 (1992).
30. Healy, F. G., Krasnoff, S. B., Wach, M., Gibson, D. M. & Loria, R. Involvement of a cytochrome P450 monooxygenase in thaxtomin A biosynthesis by Streptomyces acidiscabies. J. Bacteriol. 184, 2019-2029 (2002).