Pristinamycin I biosynthesis in Streptomyces pristinaespiralis: Molecular characterization of the first two structural peptide synthetase genes

Journal of Bacteriology

Volumn 179, Issue 3, 1997, Pages 705-713

  De Crécy Lagard, Valérie ^a,b   Blanc, Véronique ^a   Gil, Patricia ^a   Naudin, Laurent ^a   Lorenzon, Sophie ^a   Famechon, Alain ^a   Bamas Jacques, Nathalie ^a   Crouzet, Joel ^a   Thibaut, Denis ^a  

^a SANOFI   (France)

^b INSTITUT PASTEUR   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PRISTINAMYCIN;

AMINO ACID SEQUENCE; ANTIMICROBIAL ACTIVITY; ARTICLE; CARBOXY TERMINAL SEQUENCE; ENZYME ACTIVITY; FATTY ACID METABOLISM; GENETIC CODE; PRIORITY JOURNAL; PROTEIN STRUCTURE; STREPTOMYCES;

EID: 0031024022     PISSN: 00219193     EISSN: None     Source Type: Journal    
DOI: 10.1128/jb.179.3.705-713.1997     Document Type: Article

References (56)

1. Albertini, A. M., T. Caramori, F. Scoffone, C. Scotti, and A. Galizzi. 1995. Sequence around the 159° region of the Bacillus subtilis genome: the pksX locus spans 33.6 kb. Microbiology 141:299-309.
2. Aparicio, J. F., I. Molnar, T. Schwecke, A. König, S. F. Haydock, L. E. Khaw, J. Staunton, and P. F. Lead lay. 1996. Organization of the biosynthetic gene cluster for rapamycin in Streptomyces hygroscopicus: analysis of the enzymatic domains in the modular polyketide synthase. Gene 169:9-16.
3. Bamas-Jacques, N., S. Lorenzon, P. Lacroix, and J. Crouzet. Resolution of the Streptomyces pristinaespiralis chromosome by pulse-field gel electrophoresis and mapping of genes involved in pristinamycin biosynthesis and resistance. Submitted for publication.
4. A synthase and NADH:riboflavin 5′-phosphate oxidoreductase. J. Bacteriol. 177:5206-5214.
5. Chung, C. T., and H. Miller. 1988. A rapid and convenient method for the preparation and storage of competent bacterial cells. Nucleic Acids Res. 16:3580.
6. Cocito, C. G. 1979. Antibiotics of the virginiamycin family, inhibitors which contain synergistic components. Microbiol. Rev. 43:145-198.
7. Cosmina, P., F. Rodriguez, F. de Ferra, G. Grandi, M. Perego, G. Venema, and D. van Sinderen. 1993. Sequence and analysis of the genetic locus responsible for surfactin synthesis in Bacillus subtilis. Mol. Microbiol. 8:821-831.
8. Crosby, J., D. H. Sherman, M. J. Bibb, W. P. Revill, D. A. Hopwood, and T. J. Simpson. 1995. Polyketide synthase acyl carrier proteins from Streptomyces: expression in Escherichia coli, purification and partial characterisation. Biochim. Biophys. Acta 1251:32-42.
9. 8a.de Crécy-Lagard, V. Unpublished data.
10. de Crécy-Lagard, V., P. Marlière, and W. Saurin. 1995. Multienzymatic non ribosomal peptide biosynthesis: identification of the functional domains catalysing peptide elongation and epimerisation. C. R. Acad. Sci. 318:927-36.
11. Dieckmann, R., Y.-O. Lee, H. van Liempt, H. von Döhren, and H. Kleinkauf. 1995. Expression of an active-forming domain of peptide synthetases corresponding to acyl-CoA-synthetases. FEBS Lett. 357:212-216.
12. 10a.Genetics Computer Group. 1994. Program manual for the Wisconsin package, version 8. Genetics Computer Group. Madison, Wis.
13. Gibson, T. J. 1984. Studies on the Epstein-Barr virus genome. Ph.D. thesis. Cambridge University, Cambridge, England.
14. Gocht, M., and M. A. Marahiel. 1994. Analysis of core sequences in the D-Phe activating domain of the multifunctional peptide synthetase TycA by site-directed mutagenesis. J. Bacteriol. 176:2654-2662.
15. Guilvout, I., O. Mercereau-Puijalon, S. Bonnefoy, A. P. Pugsley, and E. Carniel. 1993. High-molecular-weight protein 2 of Yersinia enterolitica is homologous to AngR of Vibrio anguillarum and belongs to a family of proteins involved in nonribosomal peptide synthesis. J. Bacteriol. 175:5488-5504.
16. Haese, A., R. Pieper, T. von Ostrowski, and R. Zooher. 1994. Bacterial expression of catalytical active fragments of the multifunctional enzyme enniatin synthetase. J. Mol. Biol. 243:116-122.
17. Haese, A., M. Schubert, M. Herrmann, and R. Zocher. 1993. Molecular characterization of the enniatin synthetase gene encoding a multifunctional enzyme catalysing N-methyldepsipeptide formation in Fusarium scirpi. Mol. Microbiol. 7:905-914.
18. Higgins, D. G., A. J. Bleasby, and R. Fuchs. 1991. CLUSTAL V: improved software for multiple sequence alignment. CABIOS 8:189-191.
19. Hillemann, D., A. Pühler, and W. Wohlleben. 1991. Gene disruption and gene replacement in Streptomyces via single stranded DNA transformation of integration vectors. Nucleic Acids Res. 19:727-731.
20. Hohn, B., and J. F. Collins. 1980. A small cosmid for efficient cloning of large DNA fragments. Gene 11:291-298.
21. Hopwood, D. A., M. J. Bibb, K. F. Chater, T. Kieser, C. J. Bruton, H. M. Kieser, D. J. Lydiate, C. P. Smith, J. M. Ward, and H. Schrempf. 1985. A laboratory manual. Genetic manipulation of Streptomyces. The John Innes Foundation, Norwich, England.
22. Kao, C. M., L. Katz, and C. Khosla. 1994. Engineered biosynthesis of a complete macrolactone in a heterologous host. Science 265:509-512.
23. Katz, L., and S. Donadio, 1993. Polyketide synthesis: prospects for hybrid antibiotics. Annu. Rev. Microbiol. 47:875-912.
24. Keller, U., and W. Schlumbohm. 1992. Purification and characterization of actinomycin synthetase I, a 4-methyl-3-hydroxyanthranilic acid-AMP ligase from Streptomyces chrysomallus. J. Biol. Chem. 267:11745-11752.
25. Kleinkauf, H., and H. von Döhren. 1990. Non ribosomal biosynthesis of peptide antibiotics. Eur. J. Biochem. 192:1-15.
26. Laemmli, U. K. 1970. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature (London) 227:680-685.
27. Lipmann, F. 1971. Attempts to map a process evolution of peptide synthesis. Synthesis of peptide antibiotics from thiol-linked amino acids parallels fatty acid synthesis. Science 173:875-884.
28. MacCabe, A. P., H. van Liempt, H. Palissa, S. E. Unkles, M. B. R. Riach, E. Pfeifer, H. von Döhren, and J. R. Kinghorn. 1991. δ-(L-α-Aminoadipyl)-L-cysteinyl-D-valine synthetase from Aspergillus nidulans. Molecular characterization of the acvA gene encoding the first enzyme of the penicillin biosynthetic pathway. J. Biol. Chem. 266:12646-12654.
29. Maniatls, T. E., E. F. Fritsch, and J. Sambrook. 1989. Molecular cloning: a laboratory manual, 2nd ed. Cold Spring Harbor Laboratory, Cold Spring Harbor, N.Y.
30. Pavela-Pranvic, M., E. Pfeifer, W. Schröder, H. von Döhren, and H. Kleinkauf. 1994. Identification of the ATP-binding site in tyrocidine synthetase 1 and selective modification with fluorescein 5′-isothiocyanate. J. Biol. Chem. 269:14962-14966.
31. Pavela-Pranvic, M., E. Pfeifer, H. van Liempt, H.-J. Schafer, H. von Döhren, and H. Kleinkauf. 1994. ATP binding in peptide synthetases: determination of contact sites of the adenine moiety by photoaffinity labeling of tyrocidine synthetase 1 with 2-azidoadenosine triphosphate. Biochemistry 33:6276-6283.
32. Pavela-Vrancic, M., H. van Liempt, K. Pfeifer, W. Freist, and H. von Döhren. 1994. Nucleotide binding by multienzyme peptide synthetases. Eur. J. Biochem. 220:535-542.
33. Pfeifer, E., M. Pavela-Pranvic, H. von Döhren, and H. Kleinkauf. 1995. Characterization of tyrocidine synthetase 1 (TY1): requirement of posttranslational modification for peptide biosynthesis. Biochemistry 34:7450-7459.
34. Pridham, T. G., P. Anderson, C. Foley, L. A. Lindenfelser, C. W. Hesseltine, and R. C. Benedict. 1957. A selection media for maintenance and taxonomic study of Streptomyces. Antibiot. Annu. 1956-1957:947-953.
35. Reichert, J., M. Sakaitani, and C. T. Walsh. 1992. Characterization of EntF as a serine-activating enzyme. Protein Sci. 1:549-556.
36. Roberts, G. A., J. Staunton, and P. F. Leadlay. 1993. Heterologous expression in Escherichia coli of an intact multienzyme component of the erythromycin-producing polyketide synthase. Eur. J. Biochem. 214:305-311
37. Rusnak, F., M. Sakaitani, D. Drueckhammer, J. Reichbert, and C. T. Walsh. 1991. Biosynthesis of the Escherichia coli siderophore enterobactin: sequence of the entF gene, expression and purification of EntF, and analysis of covalent phosphopantetheine. Biochemistry 30:2916-2927.
38. Rusnak, F. W., S. Faraci, and C. T. Walsh. 1989. Subcloning, expression and purification of the enterobactin biosynthetic enzyme 2,3-dihydroxybenzoateAMP ligase: demonstration of enzyme-bound (2,3-dihydroxybenzoyl)adenylate product. Biochemistry 28:6827-6835.
39. Sanger, F., S. Nicklen, and A. R. Coulson. 1977. DNA sequencing with chain-terminating inhibitors, Proc. Natl. Acad. Sci. USA 74:5463-5467.
40. Schlumbohm, W., and U. Keller. 1990. Chromophore activating enzyme involved in the biosynthesis of the mikamycin B antibiotic etamycin from Streptomyces griseoviridus. J. Biol. Chem. 265:2156-2161.
41. Schlumbohm, W., T. Stein, C. Ullrich, J. Vater, M. Krause, M. A. Marahiel, V. Kruft, and B. Wittman-Liebold. 1991. An active serine is involved in covalent substrate amino acid binding at each reaction center of Gramicidin S synthetase. J. Biol. Chem. 266:23135-23141.
42. schwartz, D., R. Alijah, B. Nußbaumer, S. Pelzer, and W. Wohlleben. 1996. The peptide synthetase gene phsA from Streptomyces viridochromogenes is not juxtaposed with other genes involved in nonribosomal biosynthesis of peptides. Appl. Environ. Microbiol. 62:570-577.
43. Schwecke, T., J. F. Aparicio, I. Molnar, A. König, L. E. Khaw, S. F. Haydock. M. Oliynyk, P. Caffrey, J. Cortes, J. B. Lester, G. A. Bohm, J. Staunton, and P. F. Leadlay. 1995. The biosynthetic gene cluster for the polyketide immunosuppressant. Proc. Natl. Acad. Sci. USA 92:7839-7843.
44. Staab, J. F., M. F. Elkins, and C. F. Earhart. 1989. Nucleotide sequence of the Escherichia coli entE gene. FEMS Microbiol. Lett. 59:15-20.
45. Stachelhaus, T., and M. A. Marahiel. 1995. Modular structure of genes encoding multifunctional peptide synthetases required for non-ribosomal peptide synthesis. FEMS Microbiol. Lett. 125:3-14.
46. Stachelhaus, T., and M. A. Marahiel. 1995. Molecular structure of peptide synthetases revealed by dissection of the multifunctional enzyme GrsA. J Biol. Chem. 270:6163-6169.
47. Stein, T., B. Kluge, J. Vater, P. Franke, A. Otto, and B. Wittmann-Liebold. 1995. Gramicidin S synthase 1 (phenylalanine racemase), a prototype of amino acid racemases containing the cofactor 4′-phosphopantetheine. Biochemistry 34:4633-4662.
48. Stein, T., J. Vater, V. Kruft, B. Wittman-Liebold, P. Franke, M. Panico, R. McDowell, and H. R. Morris. 1994. Detection of 4′-phosphopantetheine at the thioester binding site for L-valine of gramicidin S synthetase 2. FEBS Lett. 340:39-44.
49. Stindl, A., and U. Keller. 1993. The initiation of peptide formation in the biosynthesis of actinomycin. J. Biol. Chem. 268:10612-10620.
50. Stindl, A., and U. Keller. 1994. Epimerization of the D-valine portion in the biosynthesis of actinomycin D. Biochemistry 33:9358-9364.
51. Thibaut, D., D. Bisch, N. Ratet, L. Maton, M. Couder, L. Debussehe, and F. Blanche. 1997. Purification of peptide synthetases involved in pristinamycin I biosynthesis. J. Bacteriol. 179:697-704.
52. A biosynthesis. J. Bacteriol. 177:5199-5205.
53. Turgay, K., M. Krause, and M. A. Marahiel. 1992. Four homologous domains in the primary structure of GrsB are related to domains in a super family of adenylate-forming enzymes. Mol. Microbiol. 6:529-546.
54. Vazquez, D. 1975. The streptogramin family of antibiotics. Antibiotics 3:521-534.
55. von Döhren, H., E. Pfeifer, H. von Liempt, Y.-O. Lee, M. Pavela-Vrancic, and T. Sehwecke. 1993. The non ribosomal system: what we learn from the genes encoding protein templates, p. 159-167. In R. H. Baltz, G. D. Hegeman, and P. L. Skatrud (ed.), Industrial microorganisms: basic and applied genetics. American Society for Microbiology. Washington, D.C.
56. Wakil, S. J. 1989. Fatty acid synthase, a proficient multifunctional enzyme. Biochemistry 28:4523-4530.