Heterologous expression of tylosin polyketide synthase and production of a hybrid bioactive macrolide in Streptomyces venezuelae

Applied Microbiology and Biotechnology

Volumn 72, Issue 4, 2006, Pages 763-769

  Jung, Won Seok ^a   Lee, Sang Kil ^a   Hong, Jay Sung Joong ^a   Park, Sung Ryeol ^b   Jeong, Soon Jeong ^b   Han, Ah Reum ^a   Sohng, Jae Kyung ^c   Kim, Byung Gee ^a   Choi, Cha Yong ^a   Sherman, David H ^d   Yoon, Yeo Joon ^b  

^a Seoul National University   (South Korea)

^b Ewha Womans University   (South Korea)

^c SunMoon University   (South Korea)

^d UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSYLATED TYLACTONE; MACROLACTONE; MUTANT STRAIN; STREPTOMYCES VENEZUELAE;

GENES; METABOLITES; MUTAGENESIS; PROTEINS; SUBSTRATES; TISSUE CULTURE;

ENZYME KINETICS;

ANTIBIOTIC AGENT; GLYCOSYLTRANSFERASE; LACTONE DERIVATIVE; MACROLIDE; MALONYL COENZYME A; PIKROMYCIN; POLYKETIDE SYNTHASE; TYLOSIN POLYKETIDE SYNTHASE; UNCLASSIFIED DRUG;

BACTERIUM; METABOLITE;

ARTICLE; BACTERIAL GROWTH; BACTERIAL STRAIN; BACTERIUM CULTURE; BACTERIUM MUTANT; CONTROLLED STUDY; CULTURE MEDIUM; DRUG MANUFACTURE; ENZYME SPECIFICITY; GENE CLUSTER; GENE DELETION; HETEROLOGOUS EXPRESSION; HYBRID; METABOLITE; NONHUMAN; NUCLEOTIDE SEQUENCE; PHARMACEUTICAL ENGINEERING; PLASMID; PROMOTER REGION; PROTEIN EXPRESSION; PROTEIN GLYCOSYLATION; STREPTOMYCES VENEZUELAE;

ANTI-BACTERIAL AGENTS; GENETIC ENGINEERING; MACROLIDES; MULTIENZYME COMPLEXES; PLASMIDS; STREPTOMYCES; TYLOSIN;

STREPTOMYCES; STREPTOMYCES VENEZUELAE;

EID: 33748999758     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-006-0318-5     Document Type: Article

References (39)

1. Bierman M, Logan R, O'Brien K, Seno ET, Rao RN, Schoner BE (1992) Plasmid cloning vectors for the conjugal transfer of DNA from Escherichia coli to Streptomyces spp. Gene 116:43-49
2. Borisova SA, Zhao L, Sherman DH, Liu HW (1999) Biosynthesis of desosamine: construction of a new macrolide carrying a genetically designed sugar moiety. Org Lett 1:133-136
3. Butler AR, Bate N, Kiehl DE, Kirst HA, Cundliffe E (2002) Genetic engineering of aminodeoxyhexose biosynthesis in Streptomyces fradiae. Nat Biotechnol 20:713-716
4. Elhai J, Wolk CP (1988) A versatile class of positive-selection vectors based on the nonviability of palindrome-containing plasmids that allows cloning into long polylinkers. Gene 68:119-138
5. Furumai T, Maezawa I, Matsuzawa N, Yano S, Yamaguchi T, Takeda K, Okuda T (1977) Macrolide antibiotics M-4365 produced by micromonospora I. Taxonomy, production, isolation, characterization and properties. J Antibiot 30:443-449
6. Gaisser S, Reather J, Wirtz G, Kellenberger L, Staunton J, Leadlay P (2000) A defined system for hybrid macrolide biosynthesis in Saccharopolyspora erythraea. Mol Microbiol 36:391-401
7. Hong JSJ, Park SH, Choi CY, Sohng JK, Yoon YJ (2004) New olivosyl derivatives of methymycin/pikromycin from an engineered strain of Streptomyces venezuelae. FEMS Microbiol Lett 238:291-399
8. Jung WS, Kim ES, Kang HY, Choi CY, Sherman DH, Yoon YJ (2003) Site-directed mutagenesis on putative macrolactone ring size determinant in the hybrid pikromycin-tylosin polyketide synthase. J Microbiol Biotechnol 13:823-827
9. Kieser T, Bibb MJ, Buttner MJ, Chater KF, Hoopwood DA (2000) Practical Streptomyces genetics. John Innes Centre, Norwich
10. Lee SK, Basnet DB, Hong JSJ, Jung WS, Choi CY, Lee HC, Sohng JK, Ryu KG, Kim DJ, Ahn JS, Kim BS, Oh HC, Sherman DH, Yoon YJ (2005) Structural diversification of macrolactones by substrate-flexible cytochrome P450 monooxygenase. Adv Synth Catal 347:1369-1378
11. Martin CJ, Timoney MC, Sheridan RM, Kendrew SG, Wilkinson B, Staunton J, Leadlay PF (2003) Heterologous expression in Saccharopolyspora erythraea of a pentaketide synthase derived from the spinosyn polyketide synthase. Org Biomol Chem 1:4144-4147
12. McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1993) Engineered biosynthesis of novel polyketides. Science 262: 1546-1550
13. McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1995) Rational design of aromatic polyketide natural products by recombinant assembly of enzymatic subunits. Nature 375:549-554
14. O'Hagan D (1991) The polyketide metabolites. Ellis Horwood, Chichester
15. Omura S, Ikeda H, Matsubara H, Sadakane N (1980) Hybrid biosynthesis and absolute configuration of macrolide antibiotic M-4365 G1. J Antibiot 33:1570-1572
16. Pfeifer BA, Khosla C (2001) Biosynthesis of polyketides in heterologous hosts. Microbiol Mol Biol Rev 65:106-118
17. Reeves CD, Ward SL, Revill WP, Suzuki H, Marcus M, Petrakovsky OV, Marquez S, Fu H, Dong SD, Katz L (2004) Production of hybrid 16-membered macrolides by expressing combinations of polyketide synthase genes in engineered Streptomyces fradiae hosts. Chem Biol 11:1465-1472
18. Rodriguez E, Hu Z, Ou S, Volchegursky Y, Hutchinson CR, McDaniel R (2003) Rapid engineering of polyketide overproduction by gene transfer to industrially optimized strains. J Ind Microbiol Biotechnol 30:480-488
19. Rodriguez E, Ward S, Fu H, Revil WP, McDaniel R, Katz L (2004) Engineered biosynthesis of 16-membered macrolides that require methoxymalonyl-ACP precursors in Streptomyces fradiae. Appl Microbiol Biotechnol 66:85-91
20. Rowe CJ, Cortes J, Gaisser S, Staunton J, Leadlay PF (1998) Construction of new vectors for high level expression in actinomycetes. Gene 216:215-223
21. Rude MA, Khosla C (2004) Engineered biosynthesis of polyketides in heterologous hosts. Chem Eng Sci 59:4693-4701
22. Sambrook J, Fritsch EF, Maniatis T (2001) Molecular cloning: a laboratory manual, 3rd edn. Cold Spring Harbor Laboratory, Cold Spring Harbor, NY
23. Stassi DL, Kakavas SJ, Reynolds KA, Gunawardana G, Swanson S, Zeidner D, Jackson M, Liu H, Buko A, Katz L (1998) Ethyl-substituted erythromycin derivatives produced by directed metabolic engineering. Proc Natl Acad Sci U S A 95:7305-7309
24. Stratigopoulos G, Cundliffe E (2002) Expression analysis of the tylosin-biosynthetic gene cluster: pivotal regulatory role of the tylQ product. Chem Biol 9:71-78
25. Wenzel SC, Muller R (2005) Recent developments towards the heterologous expression of complex bacterial natural product biosynthetic pathways. Curr Opin Biotechnol 16:1-13
26. Wilson DJ, Xue Y, Reynolds KA, Sherman DH (2001) Characterization and analysis of the PikD regulatory factor in the pikromycin biosynthetic pathway of Streptomyces venezuelae. J Bacteriol 183:3468-3475
27. Xue Y, Sherman DH (2000) Alternative modular polyketide synthase expression controls macrolactone structure. Nature 403:571-575
28. Xue Y, Sherman DH (2001) Biosynthesis and combinatorial biosynthesis of pikromycin-related macrolides in Streptomyces venezuelae. Metab Eng 3:15-26
29. Xue Y, Zhao L, Liu HW, Sherman DH (1998a) A gene cluster for macrolide antibiotic biosynthesis in Streptomyces venezuelae: architecture of metabolic diversity. Proc Natl Acad Sci U S A 95:12111-12116
30. Xue Y, Wilson D, Zhao L, Liu H, Sherman DH (1998b) Hydroxylation of macrolactone YC-17 and narbomycin in mediated by the pikC-encoded cytochrome P450 in Streptomyces venezuelae. Chem Biol 5:661-667
31. Xue Q, Ashley G, Hutchinson CR, Santi DV (1999) A multiplasmid approach to preparing large libraries of polyketides. Proc Natl Acad Sci U S A 96:11740-11745
32. Yamase H, Zhao L, Liu HW (2000) Engineering a hybrid sugar biosynthetic pathway: production of L-rhamnose and its implication on dihydrostreptose biosynthesis. J Am Chem Soc 122:12397-12398
33. Yoon YJ, Beck JB, Kim BS, Kang HY, Reynolds KA, Sherman DH (2002) Generation of multiple bioactive macrolides by hybrid modular polyketide synthases in Streptomyces venezuelae. Chem Biol 9:203-214
34. Yu TW, Muller R, Muller M, Zhang X, Draeger G, Kim CG, Leistner E, Floss HG (2001) Mutational analysis and reconstituted expression of the biosynthetic genes involved in the formation of 3-amino-5-hydroxybenzoic acid, starter unit of rifamycin biosynthesis in Amycolatopsis mediterranei S699. J Biol Chem 276:12546-12555
35. Zhao L, Sherman DH, Liu HW (1998a) Biosynthesis of desosamine: construction of a new methymycin/neomethymycin analogue by deletion of a desosamine biosynthetic gene. J Am Chem Soc 120:10256-10257
36. Zhao L, Que NLS, Xue Y, Sherman DH, Liu HW (1998b) Mechanistic studies of desosamine biosynthesis: C-4 deoxygenation precedes C-3 transamination. J Am Chem Soc 120: 12159-12160
37. Zhao L, Ahlert J, Xue YQ, Thorson JS, Sherman DH, Liu HW (1999) Engineering a methymycin/pikromycin-calicheamicin hybrid: construction of two new macrolides carrying a designed sugar moiety. J Am Chem Soc 121:9881-9882
38. Zhao L, Borisova SA, Yeung SM, Liu HW (2001) Study of C-4 deoxygenation in the biosynthesis of desosamine: evidence implicating a novel mechanism. J Am Chem Soc 123:7909-7910
39. Ziermann R, Betlach MC (1999) Recombinant polyketide synthesis in Streptomyces: engineering of improved host strain. Biotechniques 26:106-110