Molecular recognition of diketide substrates by a β-ketoacyl-acyl carrier protein synthase domain within a bimodular polyketide synthase

Chemistry and Biology

Volumn 4, Issue 10, 1997, Pages 757-766

  Chuck, Jo Anne ^a   McPherson, Michael ^a   Huang, Hai ^a   Jacobsen, John R ^b   Khosla, Chaitan ^b,c   Cane, David E ^a  

^a BROWN UNIVERSITY   (United States)

^b Stanford University   (United States)

^c STANFORD UNIVERSITY   (United States)

Author keywords

Erythromycin biosynthesis; Polyketide synthase; Substrate analog; ketoacyl acyl carrier protein synthase

Indexed keywords

EID: 0031259679     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(97)90314-8     Document Type: Article

References (34)

1. O'Hagan, D. (1995). The Polyketide Metabolites. Ellis Horwood, Chichester, U.K.
2. Wakil, S.J. (1989). Fatty acid synthase, a proficient multifunctional enzyme. Biochemistry 28, 4523-4530.
3. Hopwood, D.A. & Sherman, D.H. (1990). Molecular genetics of polyketides and its comparison to fatty acid biosynthesis. Annu. Rev. Genet. 24, 37-66.
4. O'Hagan, D. (1995). Biosynthesis of fatty acid and polyketide metabolites. Nat. Prod. Rep. 12, 1-32.
5. Pieper, R., Kao, C., Khosla, C., Luo, G. & Cane, D.E. (1996). Specificity and versatility in erythromycin biosynthesis. Chem. Soc. Rev. 25, 297-302.
6. 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 erythrea. Nature 348, 176-178.
7. 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.
8. Donadio, S., McAlpine, J.B., Sheldon, P.J., Jackson, M. & Katz, L. (1993). An erythromycin analog produced by reprogramming of polyketide synthesis. Proc. Natl Acad. Sci. USA 90, 7119-7123.
9. Bedford, D., Jacobsen, J.R., Luo, G., Cane, D.E. & Khosla, C. (1996). A functional chimeric modular polyketide synthase generated via domain replacement. Chem. Biol. 3, 827-831.
10. 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.
11. Cortes, J., Weismann, K.E.H., Roberts, G.A., Brown, M.J.B., Staunton, J. & Leadlay, P.P. (1995). Repositioning of a domain in a modular polyketide synthase to promote specific chain cleavage. Science 268, 1487-1489.
12. 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.
13. 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.
14. Oliynyk, M., Brown, M.J.B., Cortes, J., Staunton, J. & Leadlay, P.P. (1996). A hybrid polyketide synthase obtained by domain swapping. Chem. Biol. 3, 833-839.
15. Kuhstoss S., Huber, M., Turner, J.R, Paschal, J.W. & Rao, R.N. (1996). Production of a novel polyketide through the construction of a hybrid polyketide synthase. Gene 183, 231-236.
16. McDaniel, R., et al., & Khosla, C. (1997). Gain-of-function mutagenesis of a modular polyketide synthase. J. Am. Chem. Soc. 119, 4309-4310.
17. 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. 11. Engineered biosynthesis of an eight-membered ring tetraketide lactone. J. Am. Chem. Soc., in press.
18. Hutchinson, C.R. & Fujii, I. (1995). Polyketide synthase gene manipulation: a structure-function approach in engineering novel antibiotics. Annu. Rev. Microbiol. 49, 201-238.
19. Tsoi, C.J. & Khosla, C. (1995), Combinatorial biosynthesis of 'unnatural' natural products: the polyketide example. Chem. Biol. 2, 355-362.
20. Pieper, R., Luo, G., Cane, D.E. & Khosla, C. (1995). Cell-free biosynthesis of polyketides by recombinant erythromycin polyketide synthases. Nature 378, 263-266.
21. Weismann, K.E.H., et al., & Leadlay, P.F. (1995). Polyketide synthesis in vitro on a modular polyketide synthase. Chem. Biol. 2, 583-589.
22. Pieper, R., Ebert-Khosla, S., Cane, D. & Khosla, C. (1996). Erythromycin biosynthesis: kinetic studies on a fully active modular polyketide synthase using natural and unnatural substrates. Biochemistry 35, 2054-2060.
23. Pieper, R., Luo, G., Cane, D.E. & Khosla, C. (1995). Remarkable broad substrate specificity of a modular polyketide synthase in a cell-free system. J. Am. Chem. Soc. 117, 11373-11374.
24. Tsukamoto, N., et al., & Cane, D.E. (1996). 6-Deoxyerythronolide B synthase 1 is specifically acylated by a diketide intermediate at the β-ketoacyl-acyl carrier protein synthase domain of module 2. Biochemistry 35, 15244-15248.
25. Kao, CM., Pieper, R., Cane, D.E. & Khosla, C (1996). Evidence for two catalytically independent clusters of active sites in a functional modular polyketide synthase. Biochemistry 35, 12363-12368.
26. Fráter, G. (1979). Über die stereospezifität der alkylierung von β-hydroxycarbonsaüreestern. (Translation: The stereospecificity of alkylation of β-hydroxycarboxylic acid esters.) Helv. Chim. Acta 62, 2825-2828.
27. Evans, D.A., Bartroli, J. & Shih, T.L. (1981). Enantioselective aldol condensations. 2. Erythro-selective chiral aldol condensations via boron enolates. J. Am. Chem. Soc. 103, 2127-2129.
28. Cane, D.E., Lambalot, R.H., Prabhakaran, P.C. & Ott, W.R. (1993). Macrolide biosynthesis. 7. Incorporation of chain elongation intermediates into methymycin. J. Am. Chem. Soc. 115, 522-526.
29. Wong, H., Mattick, J.S. & Wakil, S.J. (1983). The architecture of the animal fatty acid synthetase. III. Isolation and characterization of β-ketoacyl reductase. J. Biol. Chem. 258, 15305-15311.
30. Marsden, A.F.A., Caffrey, P., Aparicio, J.F., Loughran, M.S., Staunton, J. & Leadlay, P.F. (1994). Stereospecific acyl transfers on the erythromycin-producing polyketide synthase. Science 263, 378-380.
31. 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.
32. Cane, D.E., Liang, T.-C., Taylor, P.B., Chang, C. & Yang, C.-C. (1986). Macrolide biosynthesis. 3. Stereochemistry of the chain- elongation steps of erythromycin biosynthesis. J. Am. Chem. Soc. 108, 4957-4964.
33. Ruan, X., et al., & Katz, L. (1997). Acyltransferase domain substitutions in the erythromycin polyketide synthase yield novel erythromycin derivatives. J. Bacteriol. 179, in press.
34. 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.