Mutational analysis of peptidyl carrier protein and acyl carrier protein synthase unveils residues involved in protein - Protein recognition

Biochemistry

Volumn 43, Issue 28, 2004, Pages 8946-8956

  Finking, Robert ^a,b   Mofid, Mohammad Reza ^a   Marahiel, Mohamed A ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b UNIVERSITY OF COLOGNE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYMES; FATTY ACIDS; METABOLISM; POLYPEPTIDES; SUBSTRATES; SYNTHESIS (CHEMICAL);

COVALENT BINDING; SECONDARY METABOLISM;

BIOCHEMISTRY;

4' PHOSPHOPANTETHEINYL TRANSFERASE; ACYL CARRIER PROTEIN; CARRIER PROTEIN; COENZYME A; FATTY ACID; FATTY ACID SYNTHASE; PEPTIDE SYNTHASE; POLYKETIDE SYNTHASE; SERINE; TRANSFERASE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; COVALENT BOND; ENZYME SUBSTRATE; FATTY ACID SYNTHESIS; METABOLISM; MOLECULAR RECOGNITION; MUTATIONAL ANALYSIS; PRIORITY JOURNAL; PROTEIN MODIFICATION; PROTEIN PROTEIN INTERACTION;

BACTERIAL PROTEINS; BINDING SITES; CARRIER PROTEINS; ESCHERICHIA COLI PROTEINS; KINETICS; MUTAGENESIS, SITE-DIRECTED; PEPTIDE SYNTHASES; PROTEIN BINDING; SUBSTRATE SPECIFICITY; TRANSFERASES; TRANSFERASES (OTHER SUBSTITUTED PHOSPHATE GROUPS);

EID: 3142754894     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi0496891     Document Type: Article

References (33)

1. Schwarzer, D., Finking, R., and Marahiel, M. A. (2003) Nonribosomal peptides: from genes to products, Nat. Prod. Rep. 20, 275-287.
2. Cane, D. E., and Walsh, C. T. (1999) The parallel and convergent universes of polyketide synthases and nonribosomal peptide synthetases, Chem. Biol. 6, R319-325.
3. Hopwood, D. A. (1997) Genetic Contributions to Understanding Polyketide Synthases, Chem. Rev. 97, 2465-2497.
4. Joshi, A. K., Rangan, V. S., Witkowski, A., and Smith, S. (2003) Engineering of an active animal fatty acid synthase dimer with only one competent subunit, Chem. Biol. 10, 169-173.
5. 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, 15824-15834.
6. Mofid, M. R., Finking, R., and Marahiel, M. A. (2002) Recognition of hybrid peptidyl carrier proteins/acyl carrier proteins in nonribosomal peptide synthetase modules by the 4′-phosphopantetheinyl transferases AcpS and Sfp, J. Biol. Chem. 277, 17023-17031.
7. Holak, T. A., Kearsley, S. K., Kim, Y., and Prestegard, J. H. (1988) Three-dimensional structure of acyl carrier protein determined by NMR pseudoenergy and distance geometry calculations, Biochemistry 27, 6135-6142.
8. Parris, K. D., Lin, L., Tam, A., Mathew, R., Hixon, J., Stahl, M., Fritz, C. C., Seehra, J., and Somers, W. S. (2000) Crystal structures of substrate binding to Bacillus subtilis holo-(acyl carrier protein) synthase reveal a novel trimeric arrangement of molecules resulting in three active sites, Struct. Fold Des. 8, 883-895.
9. 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, Struct. Fold Des. 8, 407-418.
10. Xu, G. Y., Tam, A., Lin, L., Hixon, J., Fritz, C. C., and Powers, R. (2001) Solution structure of B. subtilis acyl carrier protein, Structure (Cambridge) 9, 277-287.
11. Wong, H. C., Liu, G., Zhang, Y.-M., Rock, C. O., and Zheng, J. (2002) The solution structure of acyl carrier protein from Mycobacterium tuberculosis, J. Biol. Chem. 277, 15874-15880.
12. Findlow, S. C., Winsor, C., Simpson, T. J., Crosby, J., and Crump, M. P. (2003) Solution structure and dynamics of wxytetracycline polyketide synthase acyl carrier protein from Streptomyces rimosus, Biochemistry 42, 8423-8433.
13. Flaman, A. S., Chen, J. M., Van Iderstine, S. C., and Byers, D. M. (2001) Site-directed mutagenesis of Acyl carrier protein reveals amino acid residues involved in ACP structure and Acyl-ACP synthetase activity, J. Biol. Chem. 276, 35934-35939.
14. Andrec, M., Hill, R. B., and Prestgard, J. H. (1995) Amide exchange rates in Escherichia coli acyl carrier protein: correlation with protein structure and dynamics, Protein Sci. 4, 983-993.
15. Zhang, Y. M., Rao, M. S., Heath, R. J., Price, A. C., Olson, A. J., Rock, C. O., and White, S. W. (2001) Identification and analysis of the acyl carrier protein (ACP) docking site on beta-ketoacyl-ACP synthase III, J. Biol. Chem. 276, 8231-8238.
16. Lambalot, R. H., Gehring, A. M., Flugel, R. S., Zuber, P., LaCelle, M., Marahiel, M. A., Reid, R., Khosla, C., and Walsh, C. T. (1996) A new enzyme superfamily-the phosphopantetheinyl transferases, Chem. Biol. 3, 923-936.
17. Flugel, R. S., Hwangbo, Y., Lambalot, R. H., Cronan, J. E., Jr., and Walsh, C. T. (2000) Holo-(acyl carrier protein) synthase and phosphopantetheinyl transfer in Escherichia coli, J. Biol. Chem. 275, 959-968.
18. Chirgadze, N. Y., Briggs, S. L., McAllister, K. A., Fischl, A. S., and Zhao, G. (2000) Crystal structure of Streptococcus pneumoniae acyl carrier protein synthase: an essential enzyme in bacterial fatty acid biosynthesis, EMBO J. 19, 5281-5287.
19. Mootz, H. D., Finking, R., and Marahiel, M. A. (2001) 4′-Phosphopantetheine Transfer in Primary and Secondary Metabolism of Bacillus subtilis, J. Biol. Chem. 276, 37289-37298.
20. Sanchez, C., Du, L., Edwards, D. J., Toney, M. D., and Shen, B. (2001) Cloning and characterization of a phosphopantetheinyl transferase from Streptomyces verticillus ATCC15003, the producer of the hybrid peptide-polyketide antitumor drug bleomycin, Chem. Biol. 8, 725-738.
21. Mofid, M. R., Marahiel, M. A., Ficner, R., and Reuter, K. (1999) Crystallization and preliminary crystallographic studies of Sfp: a phosphopantetheinyl transferase of modular peptide synthetases, Acta Crystallogr. D: Biol. Crystallogr. 55, 1098-1100.
22. Reuter, K., Mofid, M. R., Marahiel, M. A., and Ficner, R. (1999) Crystal structure of the surfactin synthetase-activating enzyme Sfp: a prototype of the 4′-phosphopantetheinyl transferase superfamily, EMBO J. 18, 6823-6831.
23. Gehring, A. M., Lambalot, R. H., Vogel, K. W., Drueckhammer, D. G., and Walsh, C. T. (1997) Ability of Streptomyces spp. acyl carrier proteins and coenzyme A analogues to serve as substrates in vitro for E. coli holo-ACP synthase, Chem. Biol. 4, 17-24.
24. Quadri, L. E., Weinreb, P. H., Lei, M., Nakano, M. M., Zuber, P., and Walsh, C. T. (1998) Characterization of Sfp, a Bacillus subtilis phosphopantetheinyl transferase for peptidyl carrier protein domains in peptide synthetases, Biochemistry 37, 1585-1595.
25. Finking, R., Solsbacher, J., Konz, D., Schobert, M., Schäfer, A., Jahn, D., and Marahiel, M. A. (2002) Characterization of a new type of phosphopantetheinyl transferase for fatty acid and siderophore metabolism in Pseudomonas aeruginosa, J. Biol. Chem. 277, 50293-50302.
26. Keszenman-Pereyra, D., Lawrence, S., Twfieg, M. E., Price, J., and Turner, G. (2003) The npgA/cfwA gene encodes a putative 4′- phosphopantetheinyl transferase which is essential for penicillin biosynthesis in Aspergillus nidulans, Curr. Genet. 43, 186-190.
27. Mofid, M. R., Finking, R., and Marahiel, M. A. (2004) Structure-based mutational analysis of the 4′-phosphopantetheinyl transferases Sfp from Bacillus subtilis: carrier protein recognition and reaction mechanism, Biochemistry 43, 4128-4136.
28. Sambrook, J., Fritsch, E. F., and Maniatis, T. (1989) Molecular Cloning: A Laboratory Manual, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY.
29. Mootz, H. D., Schwarzer, D., and Marahiel, M. A. (2000) Construction of hybrid peptide synthetases by module and domain fusions, Proc. Natl. Acad. Sci. U.S.A. 97, 5848-5853.
30. 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, 10439-10447.
31. 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, 22773-22781.
32. McAllister, K. A., Peery, R. B., Meier, T. I., Fischl, A. S., and Zhao, G. (2000) Biochemical and molecular analyses of the Streptococcus pneumoniae acyl carrier protein synthase, an enzyme essential for fatty acid biosynthesis, J. Biol. Chem. 275, 30864-30872.
33. Joshi, A. K., Zhang, L., Rangan, V. S., and Smith, S. (2003) Cloning, expression and characterization of a human 4′-phosphopantetheinyl transferase with broad substrate specificity, J. Biol. Chem. 278, 33142-33149.