Chemoenzymatic design of acidic lipopeptide hybrids: New insights into the structure-activity relationship of daptomycin and A54145

Biochemistry

Volumn 45, Issue 35, 2006, Pages 10474-10481

  Kopp, Florian ^a   Grünewald, Jan ^a,b   Mahlert, Christoph ^a   Marahiel, Mohamed A ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINO ACIDS; ANTIBIOTICS; BIOCHEMISTRY; CATALYSTS; ENZYME KINETICS; ENZYMES;

DAPTOMYCIN; LIPOPEPTIDES; MACROCYCLIZATION; NONRIBOSOMAL PEPTIDE SYNTHETASE (NRPS);

POLYPEPTIDES;

A 54145; AMFOMYCIN; AMINO ACID; ANTIBIOTIC AGENT; ASPARTIC ACID; CALCIUM DEPENDENT ANTIBIOTIC AGENT; DAPTOMYCIN; FRIULIMICIN; LACTAM DERIVATIVE; LACTONE DERIVATIVE; LASPARTOMYCIN; LIPOPEPTIDE; PEPTIDE; SYNTHETASE; THIOESTER; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CATALYSIS; CYCLIZATION; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; NONRIBOSOMAL PEPTIDE SYNTHESIS; PRIORITY JOURNAL; SOLID PHASE SYNTHESIS; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; CATALYSIS; CYCLIZATION; DAPTOMYCIN; DRUG DESIGN; LACTAMS, MACROCYCLIC; LIPOPROTEINS; MICROBIAL SENSITIVITY TESTS; MODELS, CHEMICAL; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; PEPTIDE SYNTHASES; PEPTIDES, CYCLIC; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33748262119     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi0609422     Document Type: Article

References (23)

1. Baltz, R. H., Miao, V., and Wrigley, S. K. (2005) Natural products to drugs: Daptomycin and related lipopeptide antibiotics, Nat. Prod. Rep. 22, 717-41.
2. Berdy, J. (2005) Bioactive microbial metabolites, J. Antibiot. 58, 1-26.
3. Raja, A., LaBonte, J., Lebbos, J., and Kirkpatrick, P. (2003) Daptomycin, Nat. Rev. Drug Discovery 2, 943-4.
4. Sieber, S. A., and Marahiel, M. A. (2005) Molecular mechanisms underlying nonribosomal peptide synthesis: Approaches to new antibiotics, Chem. Rev. 105, 715-38.
5. Fukuda, D. S., Du Bus, R. H., Baker, P. J., Berry, D. M., and Mynderse, J. S. (1990) A54145, a new lipopeptide antibiotic complex: Isolation and characterization, J. Antibiot. 43, 594-600.
6. Miao, V., Coeffet-Legal, M. F., Brian, P., Brost, R., Penn, J., Whiting, A., Martin, S., Ford, R., Parr, I., Bouchard, M., Silva, C. J., Wrigley, S. K., and Baltz, R. H. (2005) Daptomycin biosynthesis in Streptomyces roseosporus: Cloning and analysis of the gene cluster and revision of peptide stereochemistry, Microbiology 151, 1507-23.
7. Miao, V., Brost, R., Chapple, J., She, K., Gal, M. F., and Baltz, R. H. (2005) The lipopeptide antibiotic A54145 biosynthetic gene cluster from Streptomyces fradiae, J. Ind. Microbiol. Biotechnol., 1-12.
8. Kohli, R. M., and Walsh, C. T. (2003) Enzymology of acyl chain macrocyclization in natural product biosynthesis, Chem. Commun., 297-307.
9. Trauger, J. W., Kohli, R. M., Mootz, H. D., Marahiel, M. A., and Walsh, C. T. (2000) Peptide cyclization catalysed by the thioesterase domain of tyrocidine synthetase, Nature 407, 215-8.
10. Mahlert, C., Sieber, S. A., Grünewald, J., and Marahiel, M. A. (2005) Chemoenzymatic approach to enantiopure streptogramin B variants: Characterization of stereoselective pristinamycin I cyclase from Streptomyces pristinaespiralis, J. Am. Chem. Soc. 127, 9571-80.
11. Grünewald, J., Sieber, S. A., Mahlert, C., Linne, U., and Marahiel, M. A. (2004) Synthesis and derivatization of daptomycin: A chemoenzymatic route to acidic lipopeptide antibiotics, J. Am. Chem. Soc. 126, 17025-31.
12. Yeh, E., Lin, H., Clugston, S. L., Kohli, R. M., and Walsh, C. T. (2004) Enhanced macrocyclizing activity of the thioesterase from tyrocidine synthetase in presence of nonionic detergent, Chem. Biol. 11, 1573-82.
13. Trauger, J. W., Kohli, R. M., and Walsh, C. T. (2001) Cyclization of backbone-substituted peptides catalyzed by the thioesterase domain from the tyrocidine nonribosomal peptide synthetase, Biochemistry 40, 7092-8.
14. Grünewald, 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.
15. 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.
16. Kohli, R. M., Walsh, C. T., and Burkart, M. D. (2002) Biomimetic synthesis and optimization of cyclic peptide antibiotics, Nature 418, 658-61.
17. Wagner, B., Baumann, M., Sieber, S. A., and Marahiel, M. A. (2006) Solvent engineering substantially enhances the chemoenzymatic production of surfactin, ChemBioChem (in press).
18. Hojati, Z., Milne, C., Harvey, B., Gordon, L., Borg, M., Fielt, F., Wilkinson, B., Sidebottom, P. J., Rudd, B. A., Hayes, M. A., Smith, C. P., and Micklefield, J. (2002) Structure, biosynthetic origin, and engineered biosynthesis of calcium-dependent antibiotics from Streptomyces coelicolor, Chem. Biol. 9, 1175-87.
19. Finking, R., and Marahiel, M. A. (2004) Biosynthesis of nonribosomal peptides, Annu. Rev. Microbiol. 58, 453-88.
20. Eliopoulos, G. M., Thauvin, C., Gerson, B., and Moellering, R. C., Jr. (1985) In vitro activity and mechanism of action of A21978C1, a novel cyclic lipopeptide antibiotic, Antimicrob. Agents Chemother. 27, 357-62.
21. Silverman, J. A., Perlmutter, N. G., and Shapiro, H. M. (2003) Correlation of daptomycin bactericidal activity and membrane depolarization in Staphylococcus aureus, Antimicrob. Agents Chemother. 47, 2538-44.
22. Laganas, V., Alder, J., and Silverman, J. A. (2003) In vitro bactericidal activities of daptomycin against Staphylococcus aureus and Enterococcus faecalis are not mediated by inhibition of lipoteichoic acid biosynthesis, Antimicrob. Agents Chemother. 47, 2682-4.
23. Boaretti, M., and Canepari, P. (1995) Identification of daptomycin-binding proteins in the membrane of Enterococcus hirae, Antimicrob. Agents Chemother. 39, 2068-72.