Catalytic self-acylation of type II polyketide synthase acyl carrier proteins

Chemistry and Biology

Volumn 5, Issue 1, 1998, Pages 35-47

  Hitchman, Timothy S ^a   Crosby, John ^a   Byrom, Kate J ^a   Cox, Russell J ^a   Simpson, Thomas J ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

Acyl carrier protein; Fatty acid synthase; Malonyl transferase; Polyketide synthase

Indexed keywords

FELIS CATUS; STREPTOMYCES; STREPTOMYCES COELICOLOR; STREPTOMYCINEAE;

EID: 0031931702     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(98)90085-0     Document Type: Article

References (43)

1. Simpson, T.J. (1995). Polyketide biosynthesis. Chem. Ind., 407-411.
2. Tsoi, C.J. & Khosla, C. (1995). Combinatorial biosynthesis of 'unnatural' natural products: the polyketide example. Chem. Biol. 2, 355-362.
3. Jacobsen, J.R., Hutchinson, C.R., Cane, D.E. & Khosla, C. (1997). Precursor-directed biosynthesis of erythromycin analogues by an engineered polyketide synthase. Science 277, 367-369.
4. Hopwood, D.A. & Sherman, D.H. (1990). Molecular genetics of polyketides and its comparison to fatty acid biosynthesis. Annu. Rev. Genet. 24, 37-66.
5. Donadio, S., Staver, M.J., McAlpine, J.B., Swanson, S.J. & Katz, L. (1991). Modular organisation of genes required for complex polyketide biosynthesis. Science 252, 675-679.
6. Jordan, P.M. & Spencer, J.B. (1993). The biosynthesis of tetraketides - enzymology, mechanism and molecular programming. Biochem. Soc. Trans. 21, 222-228.
7. Hallam, S.E., Malpartida, F. & Hopwood, D.A. (1988). DNA sequence, transcription and deduced function of a gene involved in polyketide biosynthesis in Streptomyces coelicolor. Gene 74, 305-320.
8. Fernandez-Moreno, M.A., Martinez, E., Boto, L. & Hopwood, D.A. (1992). Nucleotide sequence and deduced functions of a set co-transcribed genes of Streptomyces coelicolor,A3(2) including the polyketide synthase for actinorhodin production. J. Biol. Chem. 7, 19278-19290.
9. Fernandez-Moreno, M.A., Martinez, E., Caballero, J.L., Ichinose, K., Hopwood, D.A. & Malpartida, F. (1994). DNA-sequence and functions of the aciVI region of the actinorhodin biosynthetic gene cluster of Streptomyces coelicolor A3(2). J. Biol. Chem. 269, 24854-24863.
10. McDaniel, R., Ebert-Khosla, S., Hopwood, D.A. & Khosla, C. (1995). Rational design of aromatic polyketide natural products by recombinant assembly of enzymatic subunits. Nature 375, 549-554.
11. McDaniel, R., Ebert-Khosla, S., Hopwood, D.A. & Khosla, C. (1993). Engineered biosynthesis of novel polyketides. Science 262, 1546-1550.
12. Shen, B. & Hutchinson, C.R. (1993). Enzymatic synthesis of a bacterial polyketide from acetyl and malonyl coenzyme A. Science 262, 1535-1540.
13. Carreras, C.W., Pieper, R. & Khosla, C. (1996). Efficient synthesis of aromatic polyketides in vitro by the actinorhodin polyketide synthase. J. Am. Chem. Soc. 118, 5158-5159.
14. Khosla, C., et al., & Hopwood, D.A. (1993). Genetic construction and functional analysis of hybrid polyketide synthases containing heterologous acyl carrier proteins. J. Bacteriol. 175, 2197-2204.
15. Cox, R.J., et al., & Simpson, T.J. (1997). Post-translational modification of heterologously expressed Streptomyces acyl carrier proteins. FEBS Lett. 405, 267-272.
16. Crump, M.P., et al., & Simpson, T.J. (1997). Solution structure of the actinorhodin polyketide synthase acyl carrier protein from Streptomyces coelicolor A3(2). Biochemistry 36, 6000-6008.
17. Crump, M.P., Crosby, J., Dempsey, C.E., Murray, M., Hopwood, D.A. & Simpson, T.J. (1996). Conserved secondary structure in the actinorhodin polyketide synthase acyl carrier protein from Streptomyces coelicolor A3(2) and the fatty acid synthase acyl carrier protein from Escherichia coli. FEBS Lett. 391, 302-306.
18. Rangan, V. & Smith, S. (1996). Expression in E. coli and refolding of the malonyl-/acetyltransferase domain of the multifunctional animal fatty acid synthase. J. Biol. Chem. 271, 31749-31755.
19. Ruch, F.E. & Vagelos, R.P. (1973). The isolation and general properties of Escherichia coli malonyl coenzyme A:acyl carrier protein transacylase. J. Biol. Chem. 248, 8086-8094.
20. Joshi, V.C. & Wakil, S.J. (1971). Studies on the mechanism of fatty acid synthesis XXVI. Purification and properties of malonyl-coenzyme A:acyl carrier protein transacylase of Escherichia coli. Arch. Biochem. Biophys. 143, 493-505.
21. Knobling, A., Schiffmann, D., Sickinger, H.-D. & Schweizer, E. (1975). Malonyl and palmityl transferase-less mutants of the yeast fatty acid synthetase complex. Eur. J. Biochem. 56, 359-367.
22. Rangan, V.S. & Smith, S. (1997). Alteration of the substrate specificity of the malonyl-CoA/acetyl-CoA:acyl carrier protein S-transacylase domain of the multifunctional fatty acid synthase by mutation of a single arginine residue. J. Biol. Chem. 272, 11975-11978.
23. Haydock, S.F., et al., & Leadlay, P.F. (1995). Divergent sequence motifs correlated with the substrate specificity of (methyl)malonyl-CoA:acyl carrier protein transacylase domains in modular polyketide synthases. FEBS Lett. 374, 246-248.
24. Oliynyk, M., Brown, M.J.B., Cortes, J., Staunton, J. & Leadlay, P.F. (1996). A hybrid polyketide synthase obtained by domain swapping. Chem. Biol. 3, 833-839.
25. Revill, W.P., Bibb, M J. & Hopwood, D.A. (1995). Purification of a malonyl transferase from Streptomyces coelicolor A3(2) and analysis of its genetic determinant. J. Bacteriol. 177, 3946-3952.
26. Summers, R.G., Ali, A., Shen, B., Wessel, W.A. & Hutchinson, C.R. (1995). Malonyl coenzyme A:acyl carrier protein acyltransferase of Streptomyces glaucescens - a possible link between fatty acid and polyketide biosynthesis. Biochemistry 34, 9389-9402.
27. Revill, W.P., Bibb, M.J. & Hopwood, D.A. (1996). Relationships between fatty acid and polyketide synthases from Streptomyces coelicolor A3(2): characterisation of the fatty acid synthase acyl carrier protein. J. Bacteriol. 178, 5660-5667.
28. Crosby, J., Sherman, D.H., Bibb, M.J., Revill, W.P., Hopwood, D.A. & Simpson, T.J. (1995). Polyketide synthase acyl carrier proteins from Streptomyces - expression in Escherichia coli, purification and partial characterisation. Biochim. Biophys. Acta 1251, 32-42.
29. Bridges, A.M., Leadley, P.F., Revill, W.P. & Staunton, J. (1991). Use of electrospray mass spectrometry to assay chemical reactivity of an acyl carrier protein involved in fatty acid biosynthesis in Saccharopolyspora erythraea. J. Chem. Soc, Chem. Commun., 776-777.
30. Cronan, J.E. & Klages, A.L. (1981). Chemical synthesis of acyl thioesters of acyl carrier protein with native structure. Proc. Natl Acad. Sci. USA 78, 5440-5444.
31. McDaniel, R., Ebert-Khosla, S., Fu, H., Hopwood, D.A. & Khosla, C. (1994). Engineered biosynthesis of novel polyketides: influence of a downstream enzyme on the catalytic specificity of a minimal polyketide synthase Proc. Natl Acad. Sci. USA 91, 11542-11546.
32. Rock, C.O. & Cronan, J.E. (1996). Escherichia coli as a model for the regulation of dissociable (type II) fatty acid biosynthesis. Biochim. Biophys. Acta 1302, 1-16.
33. Andrec, M., Hill, R.B. & Prestegard, J.H. (1995). Amide exchange rates in Escherichia coli acyl carrier protein: correlation with protein structure and dynamics. Protein Sci. 4, 983-993.
34. Khosla, C., Ebert-Khosla, S. & Hopwood, D.A. (1992). Targeted gene replacements in a Streptomyces polyketide synthase gene cluster: role for the acyl carrier protein. Mol. Microbiol. 6, 3237-3249.
35. Gehring, A.M., Lambalot, R.H., Vogel, K.W., Drueckhammer, D.G. & Walsh, C.T. (1997). Ability of Streptomycetes 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.
36. Gilbert, I.H., Ginty, M., O'Neill, J.A., Simpson, T.J., Staunton, J. & Willis, C.L. (1995). Synthesis of β-keto and α,β-unsaturated N-acetylcysteamine thioesters. Biorg. Med. Chem. Lett. 5, 1587-1590.
37. Cane, D.E., Lambalot, R.H., Prabhakaran, P.C. & Ott, W.R. (1993). Macrolide biosynthesis. 7. Incorporation of polyketide chain elongation intermediates into methymycin. J. Am. Chem. Soc. 115, 522-526.
38. Fernandez-Moreno, M.A., Martinez, E., Boto, L., Hopwood, D.A. & Malpartida, F. (1992). Nucleotide sequence and deduced functions of a set of co-transcribed genes of Streptomyces coelicolor A3(2) including the polyketide synthase for the antibiotic actinorhodin. J. Biol. Chem. 267, 19278-19290.
39. Meurer, G. & Hutchinson, C.R. (1995) Functional analysis of putative β-ketoacyl: acyl carrier protein synthase and acyl transferase active site motifs in a type II polyketide synthase of Streptomyces glaucescens. J. Bacteriol. 177, 477-481.
40. Kim, E.S., Cramer, K.D., Shreve, A.L. & Sherman, D.H. (1995) Heterologous expression of an engineered biosynthetic pathway: functional dissection of type II polyketide synthase components in Streptomyces species. J. Bacteriol. 177, 1202-1207.
41. Shen, B., Summers, R.G., Gramajo, H., Bibb, M.J. & Hutchinson, C.R. (1992). Purification and characterisation of the acyl carrier protein of the Streptomyces glaucesens tetracenomycin C polyketide synthase. J. Bacteriol. 174, 3818-3821.
42. Pieper, R., Ebert-Khosla, S., Cane, D.E. & Khosla, C. (1996) Erythromycin biosynthesis: kinetic studies on a fully active modular polyketide synthase using natural and unnatural substrates. Biochemistry 35, 2054-2060.
43. Alberts, A.W., Bell, R.M. & Vagelos, P.R. (1972). Acyl carrier proteins XV. Studies of β-ketoacyl-acyl carrier protein synthetase. J. Biol. Chem. 247, 3190-3198.