Mechanism and specificity of the terminal thioesterase domain from the erythromycin polyketide synthase

Chemistry and Biology

Volumn 6, Issue 2, 1999, Pages 117-125

  Gokhale, Rajesh S ^a   Hunziker, Daniel ^a   Cane, David E ^b   Khosla, Chaitan ^a  

^a Stanford University   (United States)

^b BROWN UNIVERSITY   (United States)

Author keywords

6 deoxyerythronolide synthase; Hydrolytic specificity; N acetyl cysteamine thioester; Polyketide synthase; Thioesterase

Indexed keywords

ESCHERICHIA COLI; ILEX COOKII;

EID: 0033079834     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(99)80008-8     Document Type: Article

References (31)

1. Hopwood, D.A. (1997). Genetic contributions to understanding polyketide synthases. Chem. Rev. 97, 2465-2497.
2. Cortes, J., Haydock, S.F., Roberts, G.A., Bevitt, D.J. & Leadlay, P.F. (1990). An unusually large multifunctional polypeptide in the erythromycin-producing polyketide synthase of Saccharopolyspora erythraea. Nature 348, 176-178.
3. Donadio, S., Staver, M.J., McAlpine, J.B., Swanson, S.J. & Katz, L. (1991). Modular organization of genes required for complex polyketide biosynthesis. Science 252, 675-679.
4. Caffrey, P., Bevitt, D.J., Staunton, J. & Leadlay, P.F. (1992). Identification of DEBS1, DEBS2 and DEBS3, the multienzyme polypeptides of the erythromycin-producing polyketide synthase from Saccharopolyspora erythraea. FEBS Lett. 304, 225-228.
5. Pieper, R., Luo, G., Cane, D.E. & Khosla, C. (1995). Cell-free synthesis of polyketides by recombinant eythromycin polyketide synthase. Nature 378, 263-266.
6. Katz, L. (1997). Manipulation of modular polyketide synthases. Chem. Rev. 97, 2557-2575.
7. Khosla, C. (1997). Harnessing the biosynthetic potential of modular polyketide synthases. Chem. Rev. 97, 2577-2590.
8. Staunton, J. & Wilkinson, B. (1997). Biosynthesis of erythromycin and rapamycin. Chem. Rev. 97, 2611-2629.
9. Cortes, J., Wiesmann, K.E.H., Roberts, G.A., Brown, M.J., Staunton, J. & Leadlay, P.F. (1995). Repositioning of a domain in a modular polyketide synthase to promote specific chain cleavage. Science 268, 1487-1489.
10. Kao, C.M., Luo, G., Katz, L., Cane, D.E. & Khosla, C. (1996). Engineered biosynthesis of structurally diverse tetraketides by a trimodular polyketide synthase. J. Am. Chem. Soc. 118, 9184-9185.
11. Kao, C.M., Luo, G., Katz, L., Cane, D.E. & Khosla, C. (1995). Manipulation of macrolide ring size by directed mutagenesis of a modular polyketide synthase. J. Am. Chem. Soc. 117, 9105-9106.
12. Kao, C.M., McPherson, M., McDaniel, R.N., Fu, H., Cane, D.E. & Khosla, C. (1997). Gain of function mutagenesis of the erythromycin polyketide synthase, 2. engineered biosynthesis of an eight-membered ring tetraketide lactone. J. Am. Chem. Soc. 119, 11339-11340.
13. Jacobsen, J.R., Hutchinson, C.R., Cane, D.E. & Khosla, C. (1997). Precursor - Directed biosynthesis of erythromycin analogs by an engineered polyketide synthase. Science 277, 367-369.
14. Lawson, D.M., et al., & Derewenda, Z.S. (1994). Structure of a myristoyl-ACP-specific thioesterase from Vibrio harveyi. Biochemistry 33, 9382-9388.
15. Aggarwal, R., Caffrey, P., Leadlay, P.F., Smith, C.J. & Staunton, J. (1995). The thioesterase of the erythromycin-producing polyketide synthase: Mechanistic studies in vitro to investigate its mode of action and substrate specificity. J. Chem. Soc. Chem. Commun. 1519-1520.
16. Weissman, K.J., et al., & Leadlay, P.F. (1998). The thioesterase of the erythromycin-producing polyketide synthase: Influence of acyl chain structure on the mode of release of substrate analogues from the acyl enzyme intermediates. Angew. Chem. Int. Ed. 37, 1437-1440.
17. Caffrey, P., Green, B., Packman, L.C., Rawlings, B., Staunton, J. & Leadlay, P.F. (1991). An acyl carrier protein-thioesterase domain from the 6-deoxyerythronolide B synthase of Saccharopolyspora erythraea - High level production purification and characterization in E.coli. Eur. J. Biochem. 195, 823-830.
18. Wakil, S.J. (1989). Fatty acid synthase - A proficient multifunctional enzyme. Biochemistry 28, 4523-4530.
19. Joshi, A.K. & Smith, S. (1995). Construction, expression and characterization of a mutated animal fatty acid synthase deficient in the dehydratase function. J. Biol. Chem. 268, 22508-22513.
20. Kao, C.M., Pieper, R., Cane, D.E. & Khosla, C. (1996). Evidence for two catalytically active clusters of active sites in a functional modular polyketide synthase. J. Am. Chem. Soc. 35, 12363-12368.
21. Staunton, J., Caffrey, P., Aparicio, J.F., Roberts, G.A., Bethell, S.S. & Leadlay, P.F. (1996). Evidence for a double-helical structure for modular polyketide synthases. Nat. Struct. Biol. 3, 188-192.
22. Ferri, S.R. & Meighen, E.A. (1991). A lux-specific myristoyl transferase in luminescent bacteria related to eukaryotic serine esterases. J. Biol. Chem. 266, 12852-12857.
23. Bender, M.L. & Kezdy, F.J. (1965). Mechanism and action of proteolytic enzymes. Ann. Rev. Biochem. 34, 49-76.
24. Walsh, C. (1979). Enzymatic Reaction Mechanisms. W.H. Freeman & Co., New York.
25. Pazirandeh, M., Chirala, S.S., Wakil, S.J. (1991). Site-directed mutagenesis studies on the recombinant thioesterase domain of chicken fatty acid synthase expressed in Escherichia coli. J. Biol. Chem. 266, 20946-20952.
26. Kao, C.M., Luo, G., Katz, L., Cane, D.E. & Khosla, C. (1994). Engineered biosynthesis of a triketide lactone from an incomplete modular polyketide synthase. J. Am. Chem. Soc. 116, 11612-11613.
27. Pieper, R., Gokhale, R.S., Luo, G., Cane, D.E. & Khosla, C. (1997). Purification and characterization of bimodular and trimodular derivatives of the erythromycin polyketide synthase. Biochemistry 36, 1846-1851.
28. Guenzi, E., Galli, G., Grgurina, I., Pace, E., Ferranti, P. & Grandi, G. (1998). Coordinate transcription and physical linkage of domains in surfactant synthetase are not essential for proper assembly and activity of the multienzyme complex. J. Biol. Chem. 273, 14403-14410.
29. Neeland, G., Ounsworth, J.P., Sims, R.J. & Weiler, L. (1994). Synthesis, conformational analysis, and stereoselective reduction of 14-membered ring 3-keto lactones. J. Org. Chem. 59, 7383-7394.
30. Gokhale, R.S., Lau, J., Cane, D.E. & Khosla, C. (1998). Functional orientation of the acyltransferase domain in a module of the erythromycin polyketide synthase. Biochemistry 37, 2524-2528.
31. 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.