Photoaffinity Labeling of the N-methyltransferase Domains of Cyclosporin Synthetase

Photochemistry and Photobiology

Volumn 77, Issue 2, 2003, Pages 129-137

  Velkov, Tony ^a   Lawen, Alfons ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON 14; COMPLEMENTARY DNA; CYCLOSPORIN SYNTHETASE; METHYL GROUP; METHYLTRANSFERASE; N METHYLTRANSFERASE; PEPTIDE SYNTHASE; S ADENOSYLMETHIONINE; UNCLASSIFIED DRUG; CYCLOSPORIN A SYNTHETASE; MULTIENZYME COMPLEX;

ARTICLE; BINDING SITE; DNA DETERMINATION; DNA SEQUENCE; ENZYME PURIFICATION; GENE; GENETIC CODE; ISOTOPE LABELING; NONHUMAN; PHOTOAFFINITY LABELING; PROTEIN BINDING; PROTEIN DOMAIN; PROTEIN SYNTHESIS; SIMA GENE; STOICHIOMETRY; CHEMISTRY; ENZYME SPECIFICITY; KINETICS; METABOLISM; ULTRAVIOLET RADIATION;

KINETICS; MULTIENZYME COMPLEXES; PEPTIDE SYNTHASES; PHOTOAFFINITY LABELS; SUBSTRATE SPECIFICITY; ULTRAVIOLET RAYS;

EID: 0038672779     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2003)077<0129:PLOTNM>2.0.CO;2     Document Type: Article

References (34)

1. Borel, J. F. and P. C. Hiestand (1999) Immunomodulation: particular perspectives. Transplant. Proc. 31, 1464-1471.
2. Lawen, A. and R. Zocher (1990) Cyclosporin synthetase. The most complex peptide synthesizing multienzyme polypeptide so far described. J. Biol. Chem. 265, 11355-11360.
3. Dittmann, J., R. M. Wenger, H. Kleinkauf and A. Lawen (1994) Mechanism of cyclosporin A biosynthesis. Evidence for synthesis via a single linear undecapeptide precursor. J. Biol. Chem. 269, 2841-2846.
4. Weber, G., K. Schörgendorfer, E. Schneider-Scherzer and E. Leitner (1994) The peptide synthetase catalyzing cyclosporine production in Tolypocladium niveum is encoded by a giant 45.8-kilobase open reading frame. Curr. Genet. 26, 120-125.
5. Marahiel, M. A. (1997) Protein templates for the biosynthesis of peptide antibiotics. Chem. Biol. 4, 561-567.
6. Stachelhaus, T., A. Schneider and M. A. Marahiel (1995) Rational design of peptide antibiotics by targeted replacement of bacterial and fungal domains. Science 269, 69-72.
7. 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.
8. Stachelhaus, T., A. Hüser and M. A. Marahiel (1996) Biochemical characterization of peptidyl carrier protein (PCP), the thiolation domain of multifunctional peptide synthetases. Chem. Biol. 3, 913-921.
9. Weber, T., R. Baumgartner, C. Renner, M. A. Marahiel and T. A. Holak (2000) Solution structure of PCP, a prototype for the peptidyl carrier domains of modular peptide synthetases. Structure 8, 407-418.
10. Stachelhaus, T., H. D. Mootz, V. Bergendahl and M. A. Marahiel (1998) Peptide bond formation in nonribosomal peptide biosynthesis. Catalytic role of the condensation domain. J. Biol. Chem. 273, 22773-22781.
11. Walsh, C. T., H. Chen, T. A. Keating, B. K. Hubbard, H. C. Losey, L. Luo, C. G. Marshall, D. A. Miller and H. M. Patel (2001) Tailoring enzymes that modify nonribosomal peptides during and after chain elongation on NRPS assembly lines. Curr. Opin. Chem. Biol. 5, 525-534.
12. 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.
13. Haese, A., R. Pieper, T. von Ostrowski and R. Zocher (1994) Bacterial expression of catalytically active fragments of the multifunctional enzyme enniatin synthetase. J. Mol. Biol. 243, 116-122.
14. Konz, D. and M. A. Marahiel (1999) How do peptide synthetases generate structural diversity? Chem. Biol. 6, R39-R48.
15. Lawen, A., R. Traber, D. Geyl, R. Zocher and H. Kleinkauf (1989) Cell-free biosynthesis of new cyclosporins. J. Antibiot. (Tokyo) 42, 1283-1289.
16. Dittmann, J., F. Vaillant, H. Kleinkauf and A. Lawen (1996) Reversible denaturation of cyclosporin synthetase by urea. FEBS Lett. 380, 157-160.
17. Wessel, D. and U. I. Flügge (1984) A method for the quantitative recovery of protein in dilute solution in the presence of detergents and lipids. Anal. Biochem. 138, 141-143.
18. Laemmli, U. K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227, 680-685.
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, 248-254.
20. 50) of an enzymatic reaction. Biochem. Pharmacol. 22, 3099-3108.
21. Scatchard, G. (1949) The attractions of proteins for small molecules and ions. Ann. N.Y. Acad. Sci. 51, 660-672.
22. Koshland, D. E. Jr., G. Némethy and D. Filmer (1966) Comparison of experimental binding data and theoretical models in proteins containing subunits. Biochemistry 5, 365-385.
23. Dahlquist, F. W. (1978) The meaning of Scatchard and Hill plots. Methods Enzymol. 48, 270-299.
24. Colman, R. F. (1997) Affinity labels for NAD(P)-specific sites. Methods Enzymol. 280, 186-203.
25. 10]-cyclosporin, a cyclosporin-related peptolide, with immunosuppressive activity by a multienzyme polypeptide. J. Biol. Chem. 266, 15567-15570.
26. Hulme, E. C. and N. J. M. Birdsall (1992) Strategy and tactics in receptor-binding studies. In Receptor-Ligand Interactions: A Practical Approach (Edited by E. C. Hulme), pp. 63-176. Oxford University Press, Oxford.
27. Burmester, J., A. Haese and R. Zocher (1995) Highly conserved N-methyltransferases as an integral part of peptide synthetases. Biochem. Mol. Biol. Int. 37, 201-207.
28. Conway, A. and D. E. Koshland Jr. (1968) Negative cooperativity in enzyme action. The binding of diphosphopyridine nucleotide to glyceraldehyde 3-phosphate dehydrogenase. Biochemistry 7, 4011-4023.
29. Levitzki, A. and D. E. Koshland Jr. (1969) Negative cooperativity in regulatory enzymes. Proc. Natl. Acad. Sci. USA. 62, 1121-1128.
30. Cook, R. A. and D. E. Koshland Jr. (1970) Positive and negative cooperativity in yeast glyceraldehyde 3-phosphate dehydrogenase. Biochemistry 9, 3337-3342.
31. Tsuji, S. Y., N. Wu and C. Khosla (2001) Intermodular communication in polyketide synthases: comparing the role of protein-protein interactions to those in other multidomain proteins. Biochemistry 40, 2317-2325.
32. Gokhale, R. S., S. Y. Tsuji, D. E. Cane and C. Khosla (1999) Dissecting and exploiting intermodular communication in polyketide synthases. Science 284, 482-485.
33. Gokhale, R. S. and C. Khosla (2000) Role of linkers in communication between protein modules. Curr. Opin. Chem. Biol. 4, 22-27.
34. Tsuji, S. Y., D. E. Cane and C. Khosla (2001) Selective protein-protein interactions direct channeling of intermediates between polyketide synthase modules. Biochemistry 40, 2326-2331.