Biosynthesis of acylpeptidolactones of the daptomycin type: A comparative analysis of peptide synthetases forming A21978C and A54145

European Journal of Biochemistry

Volumn 242, Issue 3, 1996, Pages 665-673

  Wessels, Petra ^a   Von Döhren, Hans ^a   Kleinkauf, Horst ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Daptomycin biosynthesis; Lipopeptide; Multienzyme; Peptide synthetase; Protein purification

Indexed keywords

DAPTOMYCIN; PEPTIDE SYNTHASE;

AMINO ACID SEQUENCE; ARTICLE; BIOSYNTHESIS; ENZYME ACTIVITY; ENZYME PURIFICATION; IMMUNOBLOTTING; PRIORITY JOURNAL; STREPTOMYCES; STREPTOMYCES FRADIAE;

STREPTOMYCES; STREPTOMYCES FRADIAE; STREPTOMYCES ROSEOSPORUS;

EID: 0030424714     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1432-1033.1996.0665r.x     Document Type: Review

References (45)

1. Kleinkauf, H. & von Döhren, H. (1996) A nonribosomal system of peptide biosynthesis, Eur. J. Biochem. 236, 335-351.
2. Marahiel, M. A. (1992) Multidomain enzymes involved in peptide synthesis, FEBS. Lett. 307, 40-43.
3. von Döhren, H. (1995) in Genetics and biochemistry of antibiotic production (Vining, L. C. & Stuttard, C., eds) pp. 129-72, Butterworth-Heinemann, Boston.
4. von Döhren, H., Pfeifer, E., van Liempt, H., Lee, Y.-O., Pavela-Vrancic, M. & Schwecke, T. (1993) in Industrial microorganisms: basic and applied molecular genetics (Baltz, R. H., Hegeman, G. D. & Skatrud, P. L., eds) pp. 159-167, American Society of Microbiology, Washington DC.
5. Stachelhaus, T. & Marahiel, M. A. (1995) Modular structure of genes encoding multifunctional peptide synthetases required for non-ribosomal peptide synthesis, FEMS Microbiol. Lett. 125, 3-14.
6. Kleinkauf, H. & von Döhren, H. (1995) Linking peptide and polyketide biosynthesis, J. Antibiot. 48, 563-567.
7. Kleinkauf, H. & von Döhren, H. (1995) The nonribosomal peptide biosynthetic system - on the origins of structural diversity of peptides, cyclopeptides and related compounds, Antonie van Leeuwenhoek 67, 229-242.
8. Debono, M., Barnhart, M., Carrell, C. B., Hoffmann, J. A., Occolowitz, J. L., Abbott, B. J., Fukuda, D. S., Hamill, R. L., Biemann, K. & Herlihy, W. C. (1987) A21978C, a complex of new acidic peptide antibiotics: isolation, chemistry, and mass, spectral structure elucidation, J. Antibiot. 40, 761-777.
9. Debono, M., Abbott, B. J., Molloy, R. M., Fukuda, D. S., Hunt, A. H., Daupert, V. M., Counter, F. T., Ott, J. L., Carrell, C. B. & Howard, L. C. et al. (1988) Enzymatic and chemical modifications of lipopeptide antibiotic A21978C: the synthesis and evaluation of daptomycin (LY 146032), J. Antibiot. 41, 1093-1105.
10. Fukuda, D. S., Du Bus, R. H., Baker, P. J., Berry, D. M. & Mynderse, J. S. (1990) A54145, a new lipopeptide antibiotic complex: isolation and characterization, J. Antibiot. 43, 594-600.
11. Allen, N. E., Alborn, W. E. Jr & Hobbs, J. N. Jr (1991) Inhibition of membrane potential-dependent amino acid transport by daptomycin, Antimicrob. Agents. Chemother. 35, 2639-2642.
12. Canepari, P., Boaretti, M., del Mar Lleo, M. & Satta, G. (1990) Lipoteichoic acid as a new target for activity of antibiotics: mode of action of daptomycin (LY146032), Antimicrob. Agents. Chemother. 34, 1220-1226.
13. Dieckmann, R., Lee, Y. O., van Liempt, H., von Döhren, H. & Kleinkauf, H. (1995) Expression of an active adenylate-forming domain of peptide synthetases corresponding to acyl-CoA synthetases, FEBS Lett. 357, 212-216.
14. Komura, S. & Kurahashi, K. (1980) Biosynthesis of polymyxin E III. Total synthesis of polymyxin E by a cell-free enzyme system, Biochem. Bioplns. Res. Commun. 95, 1145-1151.
15. Ullrich, C., Kluge, B., Palacz, Z. & Vater, J. (1991) Cell-free biosynthesis of surfactin, a cyclic lipopeptide produced by Bacillus subtilis, Biochemistry 30, 6503-6508.
16. Menkhaus, M., Ullrich, C., Kluge, B., Vater, J., Vollenbroich, D. & Kamp, R. M. (1993) Structural and functional organization of the surfactin synthetase multienzyme system, J. Biol. Chem. 268, 7678-7684.
17. Kleinkauf, H. & von Döhren, H. (1985) in Regulation of secondary metabolite formation (Kleinkauf, H., von Döhren, H., Dornauer, H. & Nesemann, G., eds) pp. 173-207, Verlag Chemie, Weinheim.
18. Etchegaray, A. (1995) A protein-chemical and immunological approach to the study of δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine (ACV) synthetase, Thesis, University of Sheffield.
19. 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, 248-54.
20. Laemmli, U. K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4, Nature 227, 680-685.
21. Oakley, B. R., Kirsch, D. R. & Morris, N. R. (1980) A simplified ultrasensitive silver stain for detecting proteins on polyacrylamide gels, Anal. Biochem. 105, 361-63.
22. Lee, S. G. & Lipmann, F. (1975) Tyrocidine synthetase system, Methods Enzymol. 43, 585-602.
23. Keller, U. (1987) Actinomycin synthetases. Multifunctional enzymes responsible for the synthesis of the peptide chains of actinomycin, J. Biol. Chem. 262, 5852-5856.
24. Towbin, H., Staehelin, T. & Gordon, J. (1979) Electrophoretic transfer of proteins from polyacrylamide gels to nitrocellulose sheets: procedure and some applications, Proc. Natl Acad. Sci. USA 76, 4350-4354.
25. Blake, M. S., Johnston, K. H., Russell Jones, G. J. & Gotschlich, E. C. (1984) A rapid, sensitive method for detection of alkaline phosphatase-conjugated anti-antibody on Western blots, Anal. Biochem. 136, 175-179.
26. Quandt, N., Stindl, A. & Keller, U. (1993) Sodium dodecyl sulfate-polyacrylamide gel electrophoresis for M(r) estimations of high-molecular-weight polypeptides, Anal. Biochem. 214, 490-494.
27. van Liemp,. H., von Döhren, H. & Kleinkauf, H. (1989) δ-(L-α-Aminoadipyl)-L-cysteinyl-D-valine synthetase from Aspergillus nidulans. The first enzyme in penicillin biosynthesis is a multifunctional peptide synthetase, J. Biol. Chem. 264, 3680-3684.
28. Schwecke, T., Aharonowitz, Y., Palissa, H., von Döhren, H., Kleinkauf, H. & van Liempt, H. (1992) Enzymatic characterisation of the multifunctional enzyme δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine synthetase from Streptomyces clavuligerus, Eur. J. Biochem. 205, 687-694.
29. Baldwin, J. E., Shiau, C. Y., Byford, M. F. & Schofield, C. J. (1994) Substrate specifity of δ-(L-α-aminoadipoyl)-L-cysteinyl-D-valine synthetase from Cephalosporium acremonium; demonstration of the structure of several unnatural tripeptide products, Biochem. J. 301, 367-372.
30. Stindl, A. & Keller, U. (1993) The initiation of peptide formation in the biosynthesis of actinomycin, J. Biol. Chem. 268, 10 612-10 620.
31. Scott-Craig, J. S., Panaccione, D. G., Pocard, J. A. & Walton, J. D. (1992) The cyclic peptide synthetase catalyzing HC-toxin production in the filamentous fungus Cochliobolus carbonum is encoded by a 15.7-kilobase open reading frame, J. Biol. Chem. 267, 26 044-26 049.
32. van Liempt, H. (1988) Untersuchungen zur Biosynthese der β-Lactam Vorstufe δ-(L-α-aminoadipyl)-L-cysteinyl-D-Valin, Thesis, Technische Universität Berlin, Germany.
33. Kleinkauf, H. & von Döhren, H. (1990) Nonribosomal biosynthesis of peptide antibiotics, Eur. J. Biochem. 192, 1-15.
34. Billich, A. & Zocher, R. (1990) Biosynthesis of N-methylated peptides, in Biochemistry of peptide antibiotics (Kleinkauf, H. & von Döhren, H., eds) pp. 57-80, deGruyter, Berlin, New York.
35. Lawen, A. & Zocher, R. (1990) Cyclosporin synthetase. The most complex peptide synthesizing multienzyme polypeptide so far described, J. Biol. Chem. 265, 11 355-11 360.
36. 10]cyclosporin, a cyclosporin-related peptolide, with immunosuppressive activity by a multienzyme polypeptide, J. Biol. Chem. 266, 15 567-15 570.
37. Zmijewski, M. J. & Fayerman, J. T. (1995) Glycopeptides, in Genetics and biochemistry of antibiotic production (Vining, L. C. & Stuttard, C., eds) pp. 269-282, Butterworth-Heinemann, Boston.
38. Stindl, A. & Keller, U. (1994) Epimerization of the D-valine portion in the biosynthesis of actinomycin D, Biochemistry 33, 9358-9364.
39. Haese, A., Schubert, M., Herrmann, M. & Zocher, R. (1993) Molecular characterization of the enniatin synthetase gene encoding a multifunctional enzyme catalysing N-methyldepsipeptide formation in Fusarium scirpi, Mol. Microbiol. 7, 905-914.
40. Schmidt, B., Riesner, D., Lawen, A. & Kleinkauf, H. (1992) Cyclosporin synthetase is a 1.4 MDa multienzyme polypeptide. Reevaluation of the molecular mass of various peptide synthetases, FEBS Lett. 307, 355-360.
41. Weber, G., Schorgendorfer, K., Schneider Scherzer, E. & Leitner, E. (1994) The peptide synthetase catalyzing cyclosporine production in Tolypocladium niveun is encoded by a giant 45.8-kilobase open reading frame, Curr. Genet. 26, 120-125.
42. Weßels, P., Pfeifer, E., von Döhren, H., McHenney, M. A. & Baltz, R. H. (1994) A multienzyme system involved in the biosynthesis of daptomycin in Streptomyces roseosporus, Abstracts 7th International Union of Microbiology Societies Conference, p. 127, Czechoslovak Society of Microbiology, Prague.
43. Stachelhaus, T., Schneider, A. & Marahiel, M. A. (1995) Rational design of peptide antibiotics by targeted replacement of bacterial and fungal domains, Science 269, 69-72.
44. Lakey, J. H., Lea, E. J. A., Rudd, B. A. M., Wright, D. A. & Hopwood, D. A. (1983) A new channel-forming antibiotic from Streptomyces coelicolor A3(2) which requires calcium for its activity, J. Gen. Microbiol. 129, 3565-3573.
45. Bodanszky, M., Sigler, G. F. & Bodanszky, A. (1973) Structure of the peptide antibiotic amphomycin, J. Am. Chem. Soc. 95, 2352-2357.