Molecular and biochemical characterization of the protein template controlling biosynthesis of the lipopeptide lichenysin

Journal of Bacteriology

Volumn 181, Issue 1, 1999, Pages 133-140

  Konz, Dirk ^a   Doekel, Sascha ^a   Marahiel, Mohamed A ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL PROTEIN; LIPOPEPTIDE; PEPTIDE SYNTHASE; THIOL ESTER HYDROLASE;

AMINO ACID SEQUENCE; ARTICLE; BACILLUS LICHENIFORMIS; DNA SEQUENCE; ENZYME SPECIFICITY; MOLECULAR CLONING; NONHUMAN; NUCLEOTIDE SEQUENCE; OPERON; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN STRUCTURE; PROTEIN SYNTHESIS;

BACILLUS LICHENIFORMIS; BACTERIA (MICROORGANISMS); ESCHERICHIA COLI;

EID: 0032955583     PISSN: 00219193     EISSN: None     Source Type: Journal    
DOI: 10.1128/jb.181.1.133-140.1999     Document Type: Article

References (53)

1. Arima, K., A. Kakinuma, and G. Tamura. 1968. Surfactin, a crystalline peptidelipid surfactant produced by Bacillus subtilis: isolation, characterization and its inhibition of fibrin clot formation. Biochem. Biophys. Res. Commun. 31:488-494.
2. Baumgart, F., B. Kluge, C. Ullrich, J. Vater, and D. Ziessow. 1991. Identification of amino acid substitutions in the lipopeptide surfactin using 2D NMR spectroscopy. Biochem. Biophys. Res. Commun. 177:998-1005.
3. Besson, F., F. Peypoux, G. Michel, and L. Delcambe. 1977. The structure of bacillomycin L. an antibiotic from Bacillus subtilis. Eur. J. Biochem. 77:61-67. (In French.)
4. Bradford, M. M. 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72:248-254.
5. Chen, C. L., L. K. Chang, Y. S. Chang, S. T. Liu, and J. S. Tschen. 1995. Transposon mutagenesis and cloning of the genes encoding the enzymes of fengycin biosynthesis in Bacillus subtilis. Mol. Gen. Genet. 248:121-125.
6. Conti, E., T. Stachelhaus, M. A. Marahiel, and P. Brick. 1997. Structural basis for the activation of phenylalanine in the non-ribosomal biosynthesis of gramicidin S. EMBO J. 16:4174-4183.
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. Cutting, S. M., and P. B. Vander Horn. 1990. Genetic analysis, p. 27-74. In C. R. Harwood and S. M. Cutting (ed.), Molecular biological methods for Bacillus. John Wiley & Sons, New York, N.Y.
9. de Ferra, F., F. Rodriguez, O. Tortora, C. Tosi, and G. Grandi. 1997. Engineering of peptide synthetases. Key role of the thioesterase-like domain for efficient production of recombinant peptides. J. Biol. Chem. 272:25304-25309.
10. Elsner, A., H. Engert, W. Saenger, L. Hamoen, G. Venema, and F. Bernhard. 1997. Substrate specificity of hybrid modules from peptide synthetases. J. Biol. Chem. 272:4814-4819.
11. Fiechter, A. 1992. Biosurfactants: moving towards industrial application. Trends Biotechnol. 10:208-217.
12. Fujikawa, K., Y. Sakamoto, T. Suzuki, and K. Kurahashi. 1968. Biosynthesis of tyrocidine by a cell-free enzyme system of Bacillus brevis ATCC 8185. II. Amino acid substitution in tyrocidine. Biochim. Biophys. Acta 169:520-533.
13. Fuma, S., Y. Fujishima, N. Corbell, D. Souza C., M. M. Nakano, P. Zuber, and K. Yamane. 1993. Nucleotide sequence of 5′ portion of srfA that contains the region required for competence establishment in Bacillus subtilis. Nucleic Acids Res. 21:93-97.
14. Horowitz, S., J. N. Gilbert, and W. M. Griffin. 1990. Isolation and characterization of a surfactant produced by Bacillus licheniformis 86. J. Ind. Microbiol. 6:243-248.
15. Horowitz, S., and W. M. Griffin. 1991. Structural analysis Bacillus licheniformis 86 surfactant. J. Ind. Microbiol. 7:45-52.
16. Javaheri, M., G. E. Jennemann, M. J. McInerney, and R. M. Knapp. 1985. Anaerobic production of a biosurfactant by Bacillus licheniformis JF-2. Appl. Environ. Microbiol. 50:698-700.
17. Jenny, K., O. Käppeli, and A. Fiechter. 1991. Biosurfactants from Bacillus licheniformis: structural analysis and characterization. Appl. Microbiol. Biotechnol. 36:5-13.
18. Kittelberger, R., M. Altmann, and H. von Döhren. 1982. Kinetics of amino acid activation in gramicidin S synthesis, p. 209-218. In H. Kleinkauf and H. von Döhren (ed.). Peptide antibiotics, biosynthesis and functions. Walter de Gruyter, Berlin. Germany.
19. Kleinkauf, H., and H. von Döhren. 1996. A nonribosomal system of peptide biosynthesis. Eur. J. Biochem. 236:335-351.
20. Konz, D., A. Klens, K. Schörgendorfer, and M. A. Marahiel. 1997. The bacitracin biosynthesis operon of Bacillus licheniformis ATCC 10716: molecular characterization of three multi-modular peptide synthetases. Chem. Biol. 4:927-937.
21. Krätzschmar, J., M. Krause, and M. A. Marahiel. 1989. Gramicidin S biosynthesis operon containing the structural genes grsA and grsB has an open reading frame encoding a protein homologous to fatty acid thioesterases. J. Bacteriol. 171:5422-5429.
22. Lawen, A., and R. Traber. 1993. Substrate specificities of cyclosporin synthetase and peptolide SDZ 214-103 synthetase. Comparison of the substrate specificities of the related multifunctional polypeptides. J. Biol. Chem. 268: 20452-20465.
23. Lin, S. C., M. A. Minton, M. M. Sharma, and G. Georgiou. 1994. Structural and immunological characterization of a biosurfactant produced by Bacillus licheniformis JF-2. Appl. Environ. Microbiol. 60:31-38.
24. Lipmann, F. 1980. Bacterial production of antibiotic polypeptides by thiol-linked synthesis on protein templates. Adv. Microb. Physiol. 21:227-266.
25. Marahiel, M. A., T. Stachelhaus, and H. D. Mootz. 1997. Modular peptide synthetases involved in non-ribosomal peptide synthesis. Chem. Rev. 97: 2651-2673.
26. McInerney, M. J., M. Javaheri, and D. P. Nagle, Jr. 1990. Properties of the biosurfactant produced by Bacillus licheniformis strain JF-2. J. Ind. Microbiol. 5:95-101.
27. Mhammedi, A., F. Peypoux, F. Besson, and G. Michel. 1982. Bacillomycin F. a new antibiotic of iturin group: isolation and characterization. J. Antibiot. (Tokyo) 35:306-311.
28. Mootz, H. D., and M. A. Marahiel. 1997. The tyrocidine biosynthesis operon of Bacillus brevis: complete nucleotide sequence and biochemical characterization of functional internal adenylation domains. J. Bacteriol. 179:6843-6850.
29. Nishikiori, T., H. Naganawa, Y. Muraoka, T. Aoyagi, and H. Umezawa. 1986. Plipastatins: new inhibitors of phospholipase A2, produced by Bacillus cereus BMG302-fF67. III. Structural elucidations of plipastatins. J. Antibiot. (Tokyo) 39:755-761.
30. Peypoux, F., F. Besson, G. Michel, and L. Delcambe. 1981. Structure of bacillomycin D. a new antibiotic of the iturin group. Eur. J. Biochem. 118: 323-327.
31. Peypoux, F., F. Besson, G. Michel, C. Lenzen, L. Dierickx, and L. Delcambe. 1980. Characterization of a new antibiotic of the iturin group: bacillomycin D. J. Antibiot. (Tokyo) 33:1146-1149.
32. Peypoux, K. M. Guinand. G. Michel, L. Delcambe, C. Das, and E. Lederer. 1978. Structure of iturin A. a peptidelipid antibiotic from Bacillus subtilis. Biochemistry 17:3992-3996.
33. Pieper, R., H. Kleinkauf, and R. Zocher. 1992. Enniatin synthetases from different fusaria exhibiting distinct amino acid specificities. J. Antibiot. (Tokyo) 45:1273-1277.
34. Quentin, M. J., F. Besson, F. Peypoux, and G. Michel. 1982. Action of peptidolipidic antibiotics of the iturin group on erythrocytes. Effect of some lipids on hemolysis. Biochim. Biophys. Acta 684:207-211.
35. Reverchon, S., W. Nasser, and J. Robert-Baudouy. 1994. pecS: a locus controlling pectinase, cellulase and blue pigment production in Erwinia chrysanthemi. Mol. Microbiol. 11:1127-1139.
36. Riederer, B., M. Han, and U. Keller. 1996. D-Lysergyl peptide synthetase from the ergot fungus Claviceps purpurea. J. Biol. Chem. 271:27524-27530.
37. Sambrook, J., E. F. Fritsch, and T. Maniatis. 1989. Molecular cloning: a laboratory manual. 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor. N.Y.
38. Sanger, F., S. Niklen, and A. R. Coulson. 1977. DNA sequencing with chain-terminating inhibitors. Proc. Natl. Acad. Sci. USA 74:5463-5467.
39. Schneider, A., and M. A. Marahiel. 1998. Genetic evidence for a role of thioesterase domains, integrated in or associated with peptide synthetases, in non-ribosomal peptide biosynthesis in Bacillus subtilis. Arch. Microbiol. 169: 404-410.
40. Scotti, C., M. Piatti, A. Cuzzoni, P. Perani. A. Tognoni, G. Grandi, A. Galizzi, and A. M. Albertini. 1993. A Bacillus subtilis large ORF coding for a polypeptide highly similar to polyketide synthases. Gene 130:65-71.
41. Stachelhaus, T., and M. A. Marahiel. 1997. Unpublished results.
42. Stachelhaus, T., and M. A. Marahiel. 1995. Modular structure of peptide synthetases revealed by dissection of the multifunctional enzyme GrsA. J. Biol. Chem. 270:6163-6169.
43. Stock, J. B., A. J. Ninfa, and A. M. Stock. 1989. Protein phosphorylation and the regulation of adaptive responses in bacteria. Microhiol. Rev. 53:450-490.
44. Teller, L. W., S. N. Davey, and M. Morris. 1993. Analysis of hacitracin B using fast atom bombardment and tandem mass spectrometry. Biol. Mass Spectrom. 22:712-720.
45. Thomas, D. W., and T. Ito. 1969. The revised structure of the peptide antibiotic esperin. established by mass spectrometry. Tetrahedron 25:1985-1990.
46. Tognoni, A., E. Franchi, C. Magistrelli, E. Colombo, P. Cosmina, and G. Grandi. 1995. A putative new peptide synthase operon in Bacillus subtilis: partial characterization. Microbiology 141:645-648.
47. 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.
48. Turgay, K., and M. A. Marahiel. 1994. A general approach for identifying and cloning peptide synthetase genes. Pept. Res. 7:238-241.
49. Ullrich, C., B. Kluge, Z. Palacz, and J. Vater. 1991. Cell-free biosynthesis of surfactin, a cyclic lipopeptide produced by Bacillus subtilis. Biochemistry 30: 6503-6508.
50. Vanittanakom, N., and W. Loeffler. 1986. Fengycin - a novel antifungal lipopetide antibiotic produced by Bacillus subtilis F29-3. J Antibiot. (Tokyo) 39:888-901.
51. Yakimov, M. M., K. N. Timmis, V. Wray, and H. L. Fredrickson. 1995. Characterization of a new lipopeptide surfactant produced by thermotolerant and halotolerant subsurface Bacillus licheniformis BAS50. Appl. Environ. Microbiol. 61:1706-1713.
52. Yakimov, M. M., H. L. Fredrickson, and K. N. Timmis. 1996. Effect of heterogeneity of hydrophobic moieties on surface activity of lichenysin A, a lipopeptide biosurfactant from Bacillus licheniformis BAS50. Biotechnol. Appl. Biochem. 23:13-18.
53. Yakimov, M. M., and P. N. Golyshin. 1997. ComA-dependent transcriptional activation of lichenysin A synthetase promoter in Bacillus subtilis cells. Biotechnol. Prog. 13:757-761.