Rational design of polyketide natural products

Food Technology and Biotechnology

Volumn 43, Issue 4, 2005, Pages 403-410

  Kuščer, Enej ^a,b   Raspor, Peter ^a   Petković, Hrvoje ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b BIOTICA TECHNOLOGY LTD   (United Kingdom)

Author keywords

Antibiotic; Biosynthetic engineering; Erythromycin; Polyketide; Rapamycin

Indexed keywords

BIOSYNTHETIC ENGINEERINGS; BIOSYNTHETIC GENE CLUSTER; ERYTHROMYCIN; POLYKETIDE BIOSYNTHESIS; POLYKETIDES; RAPAMYCIN; SEMI-SYNTHETIC DERIVATIVES; STRUCTURAL MODIFICATIONS;

ANTIBIOTICS; BIOCHEMISTRY; CLONING; ENCODING (SYMBOLS); GENE ENCODING; KETONES;

BIOSYNTHESIS;

EID: 30444435483     PISSN: 13309862     EISSN: 13309862     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. D.A. Hopwood, Genetic contributions to understanding polyketide synthases, Chem. Rev. 97 (1997) 2465-2497.
2. R. McDaniel, M. Welch, C.R. Hutchinson, Genetic approaches to polyketide antibiotics, Chem. Rev. 105 (2005) 543-558.
3. F. Malpartida, D.A. Hopwood, Molecular cloning of the whole biosynthetic pathway of a Streptomyces antibiotic and its expression in a heterologous host, Nature, 309 (1984) 462-464.
4. J. Cort́s, S.F. Haydock, G.A. Roberts, D.J. Bevitt, P.F. Leadlay, An unusually large multifunctional polypeptide in the erythromycin-producing polyketide synthase of Saccharopolyspora erythraea, Nature, 348 (1990) 176-178.
5. S. Donadio, M.J. Staver, J.B. McAlpine, S.J. Swanson, L. Katz, Modular organization of genes required for complex polyketide biosynthesis, Science, 252 (1991) 675-679.
6. Y. Shen, P. Yoon, T.W. Yu, H.G. Floss, D. Hopwood, B.S. Moore, Ectopic expression of the minimal whiE polyketide synthase generates a library of aromatic polyketides of diverse sizes and shapes, Proc. Natl. Acad. Sci. USA, 96 (1999) 3622-3627.
7. H. Petkovic, A. Thamchaipenet, L.H. Zhou, D. Hranueli, P. Raspor, P.G. Waterman, I.S. Hunter, Disruption of an aromatase/cyclase from the oxytetracycline gene cluster of Streptomyces rimosus results in production of novel polyketides with shorter chain lengths, J. Biol. Chem. 274 (1999) 32829-32834.
8. D. Hranueli, N. Peric, B. Borovicka, S. Bogdan, J. Cullum, P.G. Waterman, I.S. Hunter, Molecular biology of polyketide biosynthesis, Food Technol. Biotechnol. 39 (2001) 203-213.
9. Y. Tang, S.C. Tsai, C. Khosla, Polyketide chain length control by chain length factor, J. Am. Chem. Soc. 125 (2003) 12708-12709.
10. R. McDaniel, S. Ebert-Khosla, D.A. Hopwood, C. Khosla, Rational design of aromatic polyketide natural products by recombinant assembly of enzymatic subunits, Nature, 375 (1995) 549-554.
11. J.R. Jacobsen, C.R. Hutchinson, D.E. Cane, C. Khosla, Precursor-directed biosynthesis of erythromycin analogs by an engineered polyketide synthase, Science, 277 (1997) 367-369.
12. A.F.A. Marsden, B. Wilkinson, J. Cortés, N.J. Dunster, J. Staunton, P.F. Leadlay, Engineering broader specificity into an antibiotic-producing polyketide synthase, Science, 279 (1998) 199-202.
13. T. Schwecke, J.F. Aparicio, I. Molnar, A. Konig, L.E. Khaw, S.F. Haydock, M. Oliynyk, P. Caffrey, J. Cortes, J.B. Lester, J. Staunton, P.F. Leadlay, The biosynthetic gene cluster for the polyketide immunosuppressant rapamycin, Proc. Natl. Acad. Sci. USA, 92 (1995) 7839-7843.
14. J. Staunton, B. Wilkinson, Biosynthesis of erythromycin and rapamycin, Chem. Rev. 97 (1997) 2611-2629.
15. P.A. Lowden, B. Wilkinson, G.A. Bohm, S. Handa, H.G. Floss, P.F. Leadlay, J. Staunton, Origin and true nature of the starter unit for the rapamycin polyketide synthase, Angew. Chem. Int. Edit. 40 (2001) 777-779.
16. P.A. Lowden, G.A. Bohm, S. Metcalfe, J. Staunton, P.F. Leadlay, New rapamycin derivatives by precursor-directed biosynthesis, Chembiochem, 5 (2004) 535-538.
17. M. Oliynyk, M.J.B. Brown, J. Cortés, J. Staunton, P.F. Leadlay, A hybrid modular polyketide synthase obtained by domain swapping, Chem. Biol. 3 (1996) 833-839.
18. R. McDaniel, A. Thamchaipenet, C. Gustafsson, H. Pu, M. Betlach, G. Ashley, Multiple genetic modifications of the erythromycin polyketide synthase to produce a library of novel »unnatural« natural products, Proc. Natl. Acad. Sci. USA, 96 (1999) 1846-1851.
19. H. Petkovic, R.E. Lill, R.M. Sheridan, B. Wilkinson, E.L. McCormick, H.A. McArthur, J. Staunton, P.F. Leadlay, S.G. Kendrew, A novel erythromycin, 6-desmethyl erythromycin D, made by substituting an acyltransferase domain of the erythromycin polyketide synthase, J. Antibiot. 56 (2003) 543-551.
20. C.D. Reeves, S. Murli, G.W. Ashley, M. Piagentini, C.R. Hutchinson, R. McDaniel, Alteration of the substrate specificity of a modular polyketide synthase acyltransferase domain through site-specific mutations, Biochemistry, 40 (2001) 15464-15470.
21. F. Del Vecchio, H. Petkovic, S.G. Kendrew, L. Low, B. Wilkinson, R. Lill, J. Cortes, B.A. Rudd, J. Staunton, P.F. Leadlay, Active-site residue, domain and module swaps in modular polyketide synthases, J. Ind. Microbiol. Biotechnol. 30 (2003) 489-194.
22. S. Donadio, M.J. Staver, J.B. McAlpine, S.J. Swanson, L. Katz, Biosynthesis of the erythromycin macrolactone and a rational approach for producing hybrid macrolides, Gene, 115 (1992) 97-103.
23. F. Schlunzen, J.M. Harms, F. Franceschi, H.A. Hansen, H. Bartels, R. Zarivach, A. Yonath, Structural basis for the antibiotic activity of ketolides and azalides, Structure, 11 (2003) 329-338.
24. L. Rodríguez, I. Aguirrezabalaga, N. Allende, A.F. Brana, C. Méndez, J.A. Salas, Engineering deoxysugar biosynthetic pathways from antibiotic-producing microorganisms: A tool to produce novel glycosylated bioactive compounds, Chem. mol. 9 (2002) 721-729.
25. S. Gaisser, R. Lill, J. Staunton, C. Méndez, J. Salas, P.F. Leadlay, Parallel pathways for oxidation of 14-membered polyketide macrolactones in Saccharopolyspora erythraea, Mol. Microbiol. 44 (2002) 771-781.
26. L. Chung, L. Liu, S. Patel, J.R. Carney, C.D. Reeves, Deletion of rapQONML from the rapamycin gene cluster of Streptomyces hygroscopicus gives production of the 16-O-desmethyl-27-desmethoxy analog, J. Antibiot. 54 (2001) 250-256.
27. M.A. Gregory, S. Gaisser, R.E. Lill, H. Hong, R.M. Sheridan, B. Wilkinson, H. Petkovic, A.J. Weston, I. Carlitti, H. L. Lee, J. Staunton, P.F. Leadlay, Isolation and characterization of pre-rapamycin, the first macrocyclic intermediate in the biosynthesis of the immunosuppressant rapamycin by S. hygroscopicus, Angew. Chem. Int. Edit. 43 (2004) 2551-2553.
28. M.A. Gregory, S. Gaisser, H. Petkovic, S. Moss, Production of polyketides and other natural products. WO 04/007709 (2004).
29. M.A. Gregory, H. Petkovic, R.E. Lill, S.J. Moss, B. Wilkinson, S. Gaisser, P.F. Leadlay, R.M. Sheridan, Mutasynthesis of novel rapamycin analogues through manipulation of a gene governing starter unit biosynthesis, Angew. Chem. Int. Edit. 44 (2005) 4757-4760.
30. D.L. Stassi, S.J. Kakavas, K.A. Reynolds, G. Gunawardana, S. Swanson, D. Zeidner, M. Jackson, H. Liu, A. Buko, L. Katz, Ethyl-substituted erythromycin derivatives produced by directed metabolic engineering, Proc. Natl. Acad. Sci. USA, 95 (1998) 7305-7309.