Improved precursor-directed biosynthesis in E. coli via directed evolution

Journal of Antibiotics

Volumn 64, Issue 1, 2011, Pages 59-64

  Lee, Ho Young ^a,d   Harvey, Colin J B ^a   Cane, David E ^b   Khosla, Chaitan ^a,c  

^a STANFORD UNIVERSITY   (United States)

^b BROWN UNIVERSITY   (United States)

^c Stanford University   (United States)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

6 deoxyerythronolide B synthase; directed evolution; erythromycin; polyketide; precursor directed biosynthesis

Indexed keywords

6 DEOXYERYTHROMYCIN D; ERYTHROMYCIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL ENGINEERING; CONTROLLED STUDY; DIRECTED MOLECULAR EVOLUTION; DRUG SYNTHESIS; ESCHERICHIA COLI; GENETIC ANALYSIS; MUTAGENESIS; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; BIOSYNTHETIC PATHWAYS; DIRECTED MOLECULAR EVOLUTION; ERYTHROMYCIN; ESCHERICHIA COLI; MASS SPECTROMETRY; MICROBIAL SENSITIVITY TESTS; PLASMIDS;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI;

EID: 79251603379     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2010.129     Document Type: Article

References (30)

1. Cane, D. E., Walsh, C. T. & Khosla, C. Harnessing the biosynthetic code: Combinations, permutations, and mutations. Science 282, 63-68 (1998).
2. Khosla, C., Gokhale, R. S., Jacobsen, J. R. & Cane, D. E. Tolerance and specificity of polyketide synthases. Annu. Rev. Biochem. 68, 219-253 (1999).
3. Tenover, F. C. et al. Vancomycin-resistant Staphylococcus aureus isolate from a patient in Pennsylvania 48, 275-280 (2004).
4. Walsh, C. T. Polyketide and nonribosomal peptide antibiotics: Modularity and versatility. Science (New York, N.Y) 303, 1805-1810 (2004).
5. Jacobsen, J. R., Hutchinson, C. R., Cane, D. E. & Khosla, C. Precursor-directed biosynthesis of erythromycin analogs by an engineered polyketide synthase. Science (New York, N.Y) 277, 367-369 (1997).
6. Cane, D. E., Kudo, F., Kinoshita, K. & Khosla, C. Precursor-directed biosynthesis: Biochemical basis of the remarkable selectivity of the erythromycin polyketide synthase toward unsaturated triketides. Chem. Biol. 9, 131-142 (2002).
7. Boddy, C. N., Hotta, K., Tse, M. L., Watts, R. E. & Khosla, C. Precursor-directed biosynthesis of epothilone in Escherichia coli 126, 7436-7437 (2004).
8. Elliott, R. L. et al. Anhydrolide macrolides. 1. Synthesis and antibacterial activity of 2,3-anhydro-6-O-methyl 11,12-carbamate erythromycin A analogues. J. Med. Chem. 41, 1651-1659 (1998).
9. Sheehan, L. S. et al. Engineering of the spinosyn PKS: Directing starter unit incorporation 69, 1702-1710 (2006).
10. Donadio, S., McAlpine, J. B., Sheldon, P. J., Jackson, M. & Katz, L. An erythromycin analog produced by reprogramming of polyketide synthesis 90, 7119-7123 (1993).
11. Jacobsen, J. R., Keatinge-Clay, A. T., Cane, D. E. & Khosla, C. Precursor-directed biosynthesis of 12-ethyl erythromycin. Bioorg. Med. Chem. 6, 1171-1177 (1998).
12. Dayem, L. C. et al. Metabolic engineering of a methylmalonyl-CoA mutase-epimerase pathway for complex polyketide biosynthesis in Escherichia coli. Biochemistry 41, 5193-5201 (2002).
13. Lowden, P. A., Bohm, G. A., Metcalfe, S., Staunton, J. & Leadlay, P. F. New rapamycin derivatives by precursor-directed biosynthesis. Chembiochem. 5, 535-538 (2004).
14. Kinoshita, K., Williard, P. G., Khosla, C. & Cane, D. E. Precursor-directed biosynthesis of 16-membered macrolides by the erythromycin polyketide synthase. J. Am. Chem. Soc. 123, 2495-2502 (2001).
15. Frykman, S., Leaf, T., Carreras, C. & Licari, P. Precursor-directed production of erythromycin analogs by Saccharopolyspora erythraea. Biotechnol. Bioeng. 76, 303-310 (2001).
16. Kinoshita, K., Pfeifer, B. A., Khosla, C. & Cane, D. E. Precursor-directed polyketide biosynthesis in Escherichia coli. Bioorg. Med. Chem. Lett. 13, 3701-3704 (2003).
17. Lee, H. Y. & Khosla, C. Bioassay-guided evolution of glycosylated macrolide antibiotics in Escherichia coli. PLoS. Biol. 5, e45 (2007).
18. Peiru, S., Menzella, H. G., Rodriguez, E., Carney, J. & Gramajo, H. Production of the potent antibacterial polyketide erythromycin C in Escherichia coli. Appl. Environ. Microbiol. 71, 2539-2547 (2005).
19. Pfeifer, B., Hu, Z., Licari, P. & Khosla, C. Process and metabolic strategies for improved production of Escherichia coli-derived 6-deoxyerythronolide B. Appl. Environ. Microbiol. 68, 3287-3292 (2002).
20. Pfeifer, B. A. & Khosla, C. Biosynthesis of polyketides in heterologous hosts. Microbiol. Mol. Biol. Rev. 65, 106-118 (2001).
21. Leaf, T. et al. Precursor-directed biosynthesis of 6-deoxyerythronolide B analogs in Streptomyces coelicolor: Understanding precursor effects. Biotechnol. Prog. 16, 553-556 (2000).
22. Greener, A., Callahan, M. & Jerpseth, B. An efficient random mutagenesis technique using an E. coli mutator strain. Mol. Biotechnol. 7, 189-195 (1997).
23. Novick, R. P. Plasmid incompatibility. Microbiol. Rev. 51, 381-395 (1987).
24. Nordstrom, K. & Austin, S. J. Mechanisms that contribute to the stable segregation of plasmids. Annu. Rev. Genet. 23, 37-69 (1989).
25. Austin, S. & Nordstrom, K. Partition-mediated incompatibility of bacterial plasmids. Cell 60, 351-354 (1990).
26. Smith, M. A. & Bidochka, M. J. Bacterial fitness and plasmid loss: The importance of culture conditions and plasmid size. Can. J. Microbiol. 44, 351-355 (1998).
27. Arini, A., Tuscan, M. & Churchward, G. Replication origin mutations affecting binding of pSC101 plasmid-encoded Rep initiator protein. J. Bacteriol. 174, 456-463 (1992).
28. Kolb, H. C., Finn, M. G. & Sharpless, K. B. Click chemistry: Diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. Engl. 40, 2004-2021 (2001).
29. Rostovtsev, V. V., Green, L. G., Fokin, V. V. & Sharpless, K. B. A stepwise huisgen cycloaddition process: Copper(I)-catalyzed regioselective 'ligation' of azides and terminal alkynes. Angew. Chem. Int. Ed. Engl. 41, 2596-2599 (2002).
30. Himo, F. et al. Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates. J. Am. Chem. Soc. 127, 210-216 (2005).