Synthesis of linear gramicidin requires the cooperation of two independent reductases

Biochemistry

Volumn 44, Issue 23, 2005, Pages 8507-8513

  Schracke, Nadine ^a   Linne, Uwe ^a   Mahlert, Christoph ^a   Marahiel, Mohamed A ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BIOSYNTHESIS; POLYPEPTIDES; SYNTHESIS (CHEMICAL);

FINAL PRODUCT; LINEAR PENTADECAPEPTIDE GRAMICIDIN; NONRIBOSOMAL PEPTIDE SYNTHETASES (NRPS); PEPTIDYL CARRIER PROTEINS (PCP);

ENZYMES;

CARBOXYL GROUP; CARRIER PROTEIN; GRAMICIDIN; OXIDOREDUCTASE; PEPTIDE SYNTHASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

AMINO ACID SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CATALYSIS; ENZYME SUBSTRATE; LINEAR SYSTEM; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN SECONDARY STRUCTURE; SYNTHESIS;

ALDEHYDE REDUCTASE; BACILLUS; CARRIER PROTEINS; GRAMICIDIN; MULTIENZYME COMPLEXES; MULTIGENE FAMILY; OXIDOREDUCTASES; PEPTIDE BIOSYNTHESIS; PEPTIDE SYNTHASES; PROTEIN STRUCTURE, TERTIARY; SUBSTRATE SPECIFICITY;

EID: 20444391730     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi050074t     Document Type: Article

References (32)

1. Sarges, R., and Witkop, B. (1965) Gramicidin A. V. The structure of valine- and isoleucine-gramicidin A. J Am. Chem. Soc. 87, 2011-2020.
2. 13C-enriched gramicidin in phosphatidylcholine vesicles, J. Mol. Biol. 143, 1-19.
3. Wallace, B. A. (1998) Recent Advances in the High-Resolution Structures of Bacterial Channels: Gramicidin A, J. Struct. Biol. 121, 123-41.
4. Kessler, N., Schuhmann, H., Morneweg, S., Linne, U., and Marahiel, M. A. (2004) The linear pentadecapeptide gramicidin is assembled by four multimodular nonribosomal peptide synthetases that comprise 16 modules with 56 catalytic domains, J. Biol. Chem. 279, 7413-7419.
5. Schwarzer, D., Finking, R., and Marahiel, M. A. (2003) Non-ribosomal peptides: from genes to products, Nat. Prod. Rep. 20, 275-87.
6. Finking, R., and Marahiel, M. A. (2004) Biosynthesis of Non-ribosomal Peptides, Annu. Rev. Microbiol. 58, 453-88.
7. Clardy, J., and Walsh, C. (2004) Lessons from natural molecules, Nature 432, 829-837.
8. Mootz, H. D., Schwarzer, D., and Marahiel, M. A. (2002) Ways of assembling complex natural products on modular nonribosomal peptide synthetases, Chembiochem. 3, 490-504.
9. Mootz, H. D., and Marahiel, M. A. (1997) The tyrocidine biosynthesis operon of Bacillus brevis: complete nucleotide sequence and biochemical characterization of functional internal adenylation domains, J. Bacteriol. 179, 6843-50.
10. Stachelhaus, T., and Marahiel, M. A. (1995) Modular structure of peptide synthetases revealed by dissection of the multifunctional enzyme GrsA, J. Biol. Chem. 270, 6163-9.
11. Stachelhaus, T., Hüser, A., and Marahiel, M. A. (1996) Biochemical characterization of peptidyl carrier protein (PCP), the thiolation domain of multifunctional peptide synthetases, Chem. Biol. 3, 913-921.
12. Weber, T., Baumgartner, R., Renner, C., Marahiel, M. A., and Holak, T. A. (2000) Solution structure of PCP, a prototype for the peptidyl carrier domains of modular peptide synthetases, Structure Fold Des. 8, 407-18.
13. Bergendahl, V., Linne, U., and Marahiel, M. A. (2002) Mutational analysis of the C-domain in nonribosomal peptide synthesis, Eur. J. Biochem. 269, 620-9.
14. Stachelhaus, T., Mootz, H. D., Bergendahl, V., and Marahiel, M. A. (1998) Peptide bond formation in nonribosomal peptide biosynthesis. Catalytic role of the condensation domain, J. Biol. Chem. 273, 22773-81.
15. Linne, U., Doekel, S., and Marahiel, M. A. (2001) Portability of epimerization domain and role of peptidyl carrier protein on epimerization activity in nonribosomal peptide synthetases, Biochemistry 40, 15824-34.
16. Linne, U., and Marahiel, M. A. (2000) Control of directionality in nonribosomal peptide synthesis: role of the condensation domain in preventing misinitiation and timing of epimerization, Biochemistry 39, 10439-47.
17. Silakowski, B., Schairer, H. U., Ehret, H., Kunze, B., Weinig, S., Nordsiek, G., Brandt, P., Blocker, H., Hofle, G., Beyer, S., and Muller, R. (1999) New lessons for combinatorial biosynthesis from myxobacteria. The myxothiazol biosynthetic gene cluster of Stigmatella aurantiaca DW4/3-1, J. Biol. Chem. 274, 37391-9.
18. Duerfahrt, T., Eppelmann, K., Muller, R., and Marahiel, M. A. (2004) Rational design of a bimodular model system for the investigation of heterocyclization in nonribosomal peptide biosynthesis, Chem. Biol. 11, 261-71.
19. Bruner, S. D., Weber, T., Kohli, R. M., Schwarzer, D., Marahiel, M. A., Walsh, C. T., and Stubbs, M. T. (2002) Structural basis for the cyclization of the lipopeptide antibiotic surfactin by the thioesterase domain SrfTE, Structure (Camb) 10, 301-10.
20. Sieber, S. A., and Marahiel, M. A. (2003) Learning from nature's drug factories: nonribosomal synthesis of macrocyclic peptides, J. Bacteriol. 185, 7036-43.
21. Pospiech, A., Cluzel, B., Bietenhader, J., and Schupp, T. (1995) A new Myxococcus xanthus gene cluster for the biosynthesis of the antibiotic saframycin Mx1 encoding a peptide synthetase, Microbiology 141, 1793-803.
22. Gaitatzis, N., Kunze, B., and Müller, R. (2001) In vitro reconstitution of the myxochelin biosynthetic machinery of Stigmatella aurantiaca Sg a15: Biochemical characterization of a reductive release mechanism from nonribosomal peptide synthetases, Proc. Natl. Acad. Sci. U.S.A. 98, 11136-11141.
23. Ehmann, D. E., Gehring, A. M., and Walsh, C. T. (1999) Lysine biosynthesis in Saccharomyces cerevisiae: mechanism of alpha-aminoadipate reductase (Lys2) involves posttranslational phosphopantetheinylation by Lys5, Biochemistry 38, 6171-7.
24. Altschul, S. F., Madden, T. L., Schaffer, A. A., Zhang, J., Zhang, Z., Miller, W., and Lipman, D. J. (1997) Gapped BLAST and PSI-BLAST: a new generation of protein database search programs, Nucleic Acids Res. 25, 3389-402.
25. Kohli, R. M., Trauger, J. W., Schwarzer, D., Marahiel, M. A., and Walsh, C. T. (2001) Generality of peptide cyclization catalyzed by isolated thioesterase domains of nonribosomal peptide synthetases, Biochemistry 40, 7099-108.
26. Sieber, S. A., Walsh, C. T., and Marahiel, M. A. (2003) Loading peptidyl-coenzyme A onto peptidyl carrier proteins: a novel approach in characterizing macrocyclization by thioesterase domains, J. Am. Chem. Soc. 125, 10862-6.
27. Bure, C., Gobert, W., Lelievre, D., and Delmas, A. (2001) In-source fragmentation of peptide aldehydes and acetals: influence of peptide length and charge state, J Mass Spectrom. 36, 1149-55.
28. Ehmann, D. E., Trauger, J. W., Stachelhaus, T., and Walsh, C. T. (2000) Aminoacyl-SNACs as small-molecule substrates for the condensation domains of nonribosomal peptide synthetases, Chem Biol. 7, 765-72.
29. Grunewald, J., Sieber, S. A., and Marahiel, M. A. (2004) Chemo- and regioselective peptide cyclization triggered by the N-terminal fatty acid chain length: the recombinant cyclase of the calcium-dependent antibiotic from Streptomyces coelicolor, Biochemistry 43, 2915-25.
30. Stachelhaus, T., Mootz, H. D., and Marahiel, M. A. (1999) The specificity-conferring code of adenylation domains in non-ribosomal peptide synthetases, Chem. Biol. 6, 493-505.
31. Gaitatzis, N., Kunze, B., and Muller, R. (2005) Novel Insights into Siderophore Formation in Myxobacteria, Chembiochem. 6, 365-374.
32. Kasahara, T., and Kato, T. (2003) Nutritional biochemistry: A new redox-cofactor vitamin for mammals, Nature 422, 832.