Engineered biosynthesis of novel polyketides: Properties of the whiE aromatase/cyclase

Nature Biotechnology

Volumn 14, Issue 3, 1996, Pages

  Alvarez, Miguel A ^a   Fu, Hong ^b   Khosla, Chaitan ^b   Hopwood, David A ^c   Bailey, James E ^a  

^a ETH ZURICH   (Switzerland)

^b Stanford University   (United States)

^c JOHN INNES CENTRE   (United Kingdom)

Author keywords

Combinatorial biosynthesis; Novel polyketides; Polyketide synthase; Streptomyces

Indexed keywords

AROMATASE; CYCLASE; POLYKETIDE; POLYKETIDE SYNTHASE; UNCLASSIFIED DRUG;

BIOSYNTHESIS; ARTICLE; CONTROLLED STUDY; MOLECULAR CLONING; NONHUMAN; OPEN READING FRAME; PRIORITY JOURNAL; STREPTOMYCES COELICOLOR;

ANTI-BACTERIAL AGENTS; BIOTECHNOLOGY; GENES, BACTERIAL; GENETIC ENGINEERING; MULTIENZYME COMPLEXES; MULTIGENE FAMILY; RECOMBINANT PROTEINS; STREPTOMYCES;

EID: 0029670331     PISSN: 10870156     EISSN: None     Source Type: Journal    
DOI: 10.1038/nbt0396-335     Document Type: Article

References (31)

1. O'Hagan, D. 1991. The Polyketide Metabolites. Ellis Horwood, Chichester, U.K.
2. Katz, L. and Donadio, S. 1993. Polyketide synthesis: prospects for hybrid antibiotics. Ann. Rev. Microbiol. 47:875-912
3. Hallam, S. E., Malpartida, F. and Hopwood, D. A. 1988. Nueleotide sequence, transcription and deduced function of a gene involved in polyketide antibiotic synthesis in Streptomyces coellcolor. Gene 74:305-320.
4. Bibb, M. J., Biro, S., Motamedi, H., Collins, J. F. and Hutchinson, C. R. 1989. Analysis of the nucleotide sequence of the Streptomyces glaucescens tcml genes provides key information about the enzymology of polyketide tetracenomycin C antibiotic biosynthesis. EMBO J. 8:2727-2736.
5. Sherman, D. H., Malpartida, F., Bibb, M. J., Kieser, H. M. Bibb, M. J. and Hopwood, D. A. 1989 Structure and deduced function of the granaticin-producing polyketide synthase gene cluster of Streptomyces violaceoruber Tu22. EMBO J. 8:2717-2725.
6. Davis, N. K. and Chater, K. F. 1990. Spore color in Streptomyces coelicolor A3(2) involves the developmentally regulated synthesis of a compound biosynthetically related to polyketide antibiotics. Mol. Microbiol. 4:1679-1692.
7. Fernández-Moreno, M. A., Martínez, E., Boto, L., Hopwood, D. A. and Malpartida, F. 1992. Nucleotide sequence and deduced functions of a set of cotranscribed genes of Streptomyces coelicolor A3(2) including the polyketide synthase for the antibiotic actinorhodin. J. Biol. Chem. 267:19278-19290.
8. Summers, R. G., Wendt-Pienkowski, E., Motamedi, H. and Hutchinson, C. R. 1992. Nucleotide sequence of the tcmII-tcmIV region of the tetracenomycin biosynthetic gene cluster of Streptomyces glaucescens and evidence that the (cmN gene encodes a multifunctional cyclase-dehydratase-O-methyltransferase. J. Bacteriol. 174:1810-1820.
9. Bergh, S. and Uhlen, M. 1992. Analysis of a polyketide synthesis encoding gene cluster of Streptomyces curacoi. Gene 117:131-136.
10. Summers, R. G., Wendt-Pienkowski, E., Motamedi, H. and Hutchinson, C. R. 1993. The tcmVI region of the tetracenomycin C biosynthetic gene cluster of Streptomyces glaucescens encodes the tetracenomycin F1 monooxygenase, tetracenomycin F2 cyclase, and, most likely, a second cyclase. J. Bacteriol. 175:7571-7580.
11. Blanco, G., Brian, P., Pereda, A., Méndez, C., Salas, J. A. and Chater, K. F. 1993. Hybridization and DNA sequence analyses suggest an early evolutionary divergence of related biosynthetic gene sets encoding polyketide antibiotics and spore pigments in Streptomyces spp. Gene 130:107-116.
12. Yu, T. W., Bibb, M. J., Revill, W. P. and Hopwood, D. A. 1994. Cloning, sequencing, and analysis of the griseusin polyketide synthase gene cluster from Streptomyces griseus. J. Bacteriol. 176:2627-2634.
13. Bibb, M. J., Sherman, D. H., Omura, S. and Hopwood, D. A. 1994. Cloning, sequencing and deduced functions of a cluster of Streptomyces genes probably encoding biosynthesis of the polyketide antibiotic frenolicin. Gene 142:31-39.
14. Kim, E. S., Bibb, M. J., Butler, M. J , Hopwood, D. A. and Sherman, D. H. 1994. Sequences of the oxytetracycline polyketide synthase-encoding otc genes from Streptomyces nmosus. Gene 141:141-142.
15. Ye, J., Dickens, M. L., Plater, R., Li, Y., Lawrence, J. and Strohl, W. R. 1994. Isolation and sequence analysis of polyketide synthase genes from the daunomycin-producing Streptomyces sp. strain C5. J. Bacteriol. 176:6270-6280.
16. Grim, A., Madduri, K., All, A. and Hutchinson, C. R. 1994. Characterization of the Streptomyces peucetius ATCC 29050 genes encoding doxorubicin polyketide synthase. Gene 151:1-10.
17. McDaniel, R., Khosla, E., Hopwood, D. A and Khosla, C. 1993. Engineered biosynthesis of novel polyketides. Science 262:1546-1550.
18. McDaniel, R , Khosla, E., Hopwood, D. A. and Khosla, C. 1993. Engineered biosynthesis of novel polyketides: manipulation and analysis of an aromatic polyketide synthase with unproven catalytic specificities. J. Am. Chem. Soc. 115:11671-11675.
19. Fu, H., Khosla, E., Hopwood, D. A. and Khosla, C. 1994. Engineered biosynthesis of novel polyketides: dissection of the catalytic specificity of the act ketoreductase. J. Am. Chem. Soc. 116:4166-4170.
20. Fu, H., Hopwood, D. A. and Khosla, G. 1994. Engineered biosynthesis of novel polyketides: evidence for temporal, but not regiospecific, control of cyclization of an aromatic polyketide precursor. Chem. Biol. 1:205-210.
21. Fu, H., McDaniel, R., Hopwood, D. A. and Khosla, C. 1994. Engineered biosynthesis of novel polyketides: stereochemical course of two reactions catalyzed by a polyketide synthase. Biochemistry 33:9321-9326.
22. Fu, H., Khosla, E., Hopwood, D. A. and Khosla, C. 1994. Relaxed specificity of the oxytetracycline polyketide synthase for an acetate primer in the absence of a malonamyl primer. J. Am. Chem. Soc. 110:6443-6444.
23. McDaniel, R., Khosla, E., Hopwood, D. A and Khosla, C. 1994. Engineered biosynthesis of novel polyketides: the acfVII and acfIV genes encode aromatase and cyclase enzymes, respectively. J. Am. Chem. Soc. 116:10855-10859.
24. McDaniel, R., Khosla, E., Fu, H., Hopwood, D. A and Khosla, C. 1994. Engineered biosynthesis of novel polyketides: influence of a downstream enzyme on the catalytic specificity of a minimal aromatic polyketide synthase. Proc. Natl. Acad Sci. USA 91:11542-11546.
25. McDaniel, R , Hutchinson, C. R. and Khosla, C. Engineered biosynthesis of novel polyketides: analysis of tcmN function in tetracenomycin biosynthesis. J. Am. Chem. Soc. 117:6805-6810.
26. McDaniel, R., Khosla, E., Hopwood, D. A. and Khosla, C. 1995. Rational design of aromatic polyketide natural products by recombinant assembly of enzymatic subunits. Nature 375:549-554.
27. Yu, T.-W. 1995. Physical and functional studies of polyketide synthesis genes of Streptomyces. Ph.D. thesis, University of East Anglia, Norwich, U.K.
28. Tsoi, C. J. and Khosla, C. 1995. Combinatorial biosynthesis of "unnatural" natural products: the polyketide example. Chem. & Biol. 2:355-362.
29. Cerdá-Olmedo, E. 1994. The genetics of chemical diversity. Crit. Revs. in Microbiol. 20:151-160.
30. Maniatis, T., Fritsch, E. F. and Sambrook, J. 1982. Molecular Cloning: A Laboratory Manual, Cold Spring Harbor Laboratory, Cold Spring Harbor, New York.
31. Hopwood, D. A., Bibb, M. J., Chater, K. F., Kieser, T., Bruton, C. J., Kieser, H. M., Lydiate, D. J., Smith, C. P., Ward, J. M. and Schrempf, H. 1985. Genetic Manipulation of Streptomyces: A Laboratory Manual. The John Innes Foundation: Norwich, U.K.