Platensimycin and platencin biosynthesis in streptomyces platensis, showcasing discovery and characterization of novel bacterial diterpene synthases

Methods in Enzymology

Volumn 515, Issue , 2012, Pages 163-186

  Smanski, Michael J ^a   Peterson, Ryan M ^a,b   Shen, Ben ^a,b  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Biosynthesis; Diterpene synthase; ent Atiserene; ent Kaurene; Geranylgeranyl diphosphate; Platencin; Platensimycin

Indexed keywords

BACTERIAL DNA; BACTERIAL ENZYME; COPALYL DIPHOSPHATE SYNTHASE; DITERPENE SYNTHASE; DITERPENOID; GERANYLGERANIOL; GERANYLGERANYL PYROPHOSPHATE; KAURAN 16 OL SYNTHASE; PLATENCIN; PLATENCIN T1; PLATENCIN T2; PLATENSIMYCIN; PLATENSIMYCIN T1; PLATENSIMYCIN T2; PLATENSIMYCIN T3; SYNTHETASE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GENE; BACTERIAL STRAIN; BACTERIUM MUTANT; BIOINFORMATICS; BIOSYNTHESIS; DNA SEQUENCE; ENZYME ANALYSIS; ENZYME STRUCTURE; ENZYME SYNTHESIS; GENE CASSETTE; GENE DELETION; GENE OVEREXPRESSION; GENETIC ENGINEERING; GENOTYPE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FUNCTION; PROTON NUCLEAR MAGNETIC RESONANCE; SEQUENCE ANALYSIS; STREPTOMYCES; STREPTOMYCES PLATENSIS; STRUCTURE ANALYSIS;

BACTERIA (MICROORGANISMS); FUNGI; STREPTOMYCES PLATENSIS;

EID: 84866488799     PISSN: 00766879     EISSN: 15577988     Source Type: Book Series    
DOI: 10.1016/B978-0-12-394290-6.00008-2     Document Type: Chapter

References (52)

1. J. Bohlmann, G. Meyer-Gauen, and R. Croteau Plant terpenoid synthases: Molecular biology and phylogenetic analysis Proceedings of the National Academy of Sciences of the United States of America 95 1998 4126 4133 (Pubitemid 28207876)
2. P.L. Cavender Ph.D. thesis 1977 University of Illinois Urbana, IL
3. Y. Chen, M.J. Smanski, and B. Shen Improvement of secondary metabolite production in Streptomyces by manipulating pathway regulation Applied Microbiology and Biotechnology 86 2010 19 25
4. Y. Chen, E. Wendt-Pienkowski, and B. Shen Identification and utility of FdmR1 as a Streptomyces antibiotic regulatory activator for fredericamycin production in Streptomyces griseus ATCC 49344 and heterologous hosts Journal of Bacteriology 190 2008 5587 5596
5. D.W. Christianson Structural biology and chemistry of the terpenoid cyclases Chemical Reviews 106 2006 3412 3442 (Pubitemid 44376943)
6. D.W. Christianson Unearthing the roots of the terpenome Current Opinion in Chemical Biology 12 2008 141 150
7. R.H. Cornforth, and G. Popjak Chemical syntheses of substrates of sterol biosynthesis Methods in Enzymology 15 1969 359 390
8. A. Cyr, P.R. Wilderman, M. Determan, and R.J. Peters A modular approach for facile biosynthesis of labdane-related diterpenes Journal of the American Chemical Society 129 2007 6684 6685 (Pubitemid 46847494)
9. T. Dairi Studies on biosynthetic genes and enzymes of isoprenoids produced by actinomycetes The Journal of Antibiotics 58 2005 227 243 (Pubitemid 40740598)
10. T. Dairi, Y. Hamano, T. Kuzuyama, N. Itoh, K. Furihata, and H. Seto Eubacterial diterpene cyclase genes essential for production of the isoprenoid antibiotic terpentecin Journal of Bacteriology 183 2001 6085 6094 (Pubitemid 32917428)
11. L.L. Danilov, T.N. Druzhinina, N.A. Kalinchuk, S.D. Maltsev, and V.N. Shibaev Polyprenyl phosphates: Synthesis and structure-activity relationship for a biosynthetic system of Salmonella anatum O-specific polysaccharide Chemistry and Physics of Lipids 51 1989 191 203 (Pubitemid 20011723)
12. M. Daum, S. Herrmann, B. Wilkinson, and A. Bechthold Genes and enzymes involved in bacterial isoprenoid biosynthesis Current Opinion in Chemical Biology 13 2009 180 188
13. V.J. Davisson, A.B. Woodside, and C.D. Poulter Synthesis of allylic and homoallylic isoprenoid pyrophosphates Methods in Enzymology 110 1985 130 144 (Pubitemid 15100802)
14. C. Durr, H.J. Schnell, A. Luzhetskyy, R. Murillo, M. Weber, and K. Welzel Biosynthesis of the terpene phenalinolactone in Streptomyces sp. Tu6071: Analysis of the gene cluster and generation of derivatives Chemistry & Biology 13 2006 365 377
15. B. Felicetti, and D.E. Cane Aristolochene synthase: Mechanistic analysis of active site residues by site-directed mutagenesis Journal of the American Chemical Society 126 2004 7212 7221 (Pubitemid 38747771)
16. Z. Feng, L. Wang, S.R. Rajski, Z. Xu, M.F. Coeffet-LeGal, and B. Shen Engineered production of iso-migrastatin in heterologous Streptomyces hosts Bioorganic & Medicinal Chemistry 17 2009 2147 2153
17. B.T. Greenhagen, P.E. O'Maille, J.P. Noel, and J. Chappell Identifying and manipulating structural determinates linking catalytic specificities in terpene synthases Proceedings of the National Academy of Sciences of the United States of America 103 2006 9826 9831 (Pubitemid 43993582)
18. M. Gribskov, J. Devereux, and R.R. Burgess The codon preference plot: Graphic analysis of protein coding sequences and prediction of gene expression Nucleic Acids Research 12 1984 539 549
19. B. Gust, G.L. Challis, K. Fowler, T. Kieser, and K.F. Chater PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin Proceedings of the National Academy of Sciences of the United States of America 100 2003 1541 1546 (Pubitemid 36254483)
20. Y. Hamano, T. Kuzuyama, N. Itoh, K. Furihata, H. Seto, and T. Dairi Functional analysis of eubacterial diterpene cyclases responsible for biosynthesis of a diterpene antibiotic, terpentecin The Journal of Biological Chemistry 277 2002 37098 37104
21. Y. Hayashi, N. Matsuura, H. Toshima, N. Itoh, J. Ishikawa, and Y. Mikami Cloning of the gene cluster responsible for the biosynthesis of brasilicardin A, a unique diterpenoid The Journal of Antibiotics 61 2008 164 174
22. Y. Hayashi, T. Toyomasu, Y. Hirose, Y. Onodera, W. Mitsuhashi, and H. Yamane Comparison of the enzymatic properties of ent-copalyl diphosphate synthases in the biosynthesis of phytoalexins and gibberellins in rice Bioscience, Biotechnology, and Biochemistry 72 2008 523 530 (Pubitemid 351355944)
23. H. Hemmi, M. Noike, T. Nakayama, and T. Nishino An alternative mechanism of product chain-length determination in type III geranylgeranyl diphosphate synthase European Journal of Biochemistry 270 2003 2186 2194 (Pubitemid 36605569)
24. K.B. Herath, A.B. Attygalle, and S.B. Singh Biosynthetic studies of platensimycin Journal of the American Chemical Society 129 2007 15422 15423
25. K.B. Herath, A.B. Attygalle, and S.B. Singh Biosynthetic studies of platencin Tetrahedron Letters 49 2008 5755 5758
26. C. Ikeda, Y. Hayashi, N. Itoh, H. Seto, and T. Dairi Functional analysis of eubacterial ent-copalyl diphosphate synthase and pimara-9 (11), 15-diene synthase with unique primary sequences Journal of Biochemistry 141 2007 37 45 (Pubitemid 46580153)
27. H. Kawaide, R. Imai, T. Sassa, and Y. Kamiya ent-Kaurene synthase from the fungus Phaeosphaeria sp. L487 cDNA isolation, characterization, and bacterial expression of a bifunctional diterpene cyclase in fungal gibberellin biosynthesis The Journal of Biological Chemistry 272 1997 21706 21712 (Pubitemid 27382783)
28. T. Kawasaki, Y. Hayashi, T. Kuzuyama, K. Furihata, N. Itoh, and H. Seto Biosynthesis of a natural polyketide-isoprenoid hybrid compound, furaquinocin A: Identification and heterologous expression of the gene cluster Journal of Bacteriology 188 2006 1236 1244 (Pubitemid 43228655)
29. R.K. Keller, and R. Thompson Rapid synthesis of isoprenoid diphosphates and their isolation in one step using either thin layer or flash chromatography Journal of Chromatography 645 1993 161 167 (Pubitemid 23245457)
30. T. Kieser, M. Bibb, M.J. Buttner, K.F. Chater, and D.A. Hopwood Practical Streptomyces genetics 2000 The John Innes Foundation Norwich, UK
31. W. Liu, and B. Shen Genes for production of the enediyne antitumor antibiotic C-1027 in Streptomyces globisporus are clustered with the cagA gene that encodes the C-1027 apoprotein Antimicrobial Agents and Chemotherapy 44 2000 382 392 (Pubitemid 30060735)
32. D. Morrone, J. Chambers, L. Lowry, G. Kim, A. Anterola, and K. Bender Gibberellin biosynthesis in bacteria: Separate ent-copalyl diphosphate and ent-kaurene synthases in Bradyrhizobium japonicum FEBS Letters 583 2009 475 480
33. T. Nakano, and C. Djerassi Terpenoids. XLVI. Copalic acid The Journal of Organic Chemistry 26 1961 167 173
34. P.E. O'Maille, A. Malone, N. Dellas, B.A. Hess Jr., L. Smentek, and I. Sheehan Quantitative exploration of the catalytic landscape separating divergent plant sesquiterpene synthases Nature Chemical Biology 4 2008 617 623
35. K. Ogura, and T. Koyama Enzymatic aspects of isoprenoid chain elongation Chemical Reviews 98 1998 1263 1276
36. S.I. Ohnuma, H. Hemmi, C. Ohto, H. Nakane, and T. Nishino Effects of random mutagenesis in a putative substrate-binding domain of geranylgeranyl diphosphate synthase upon intermediate formation and substrate specificity Journal of Biochemistry 121 1997 696 704 (Pubitemid 27170853)
37. R.J. Peters Two rings in them all: The labdane-related diterpenoids Natural Product Reports 27 2010 1521 1530
38. S. Prisic, M. Xu, P.R. Wilderman, and R.J. Peters Rice contains two disparate ent-copalyl diphosphate synthases with distinct metabolic functions Plant Physiology 136 2004 4228 4236
39. J. Sambrook, and D. Russel Molecular cloning: A laboratory guide 3rd ed. 2001 Cold Spring Harbor Laboratory Press Cold Spring Harbor, NY
40. M.J. Smanski, R.M. Peterson, S. Huang, and B. Shen Bacterial diterpene synthases: New opportunities for mechanistic enzymology and engineered biosynthesis Current Opinion in Chemical Biology 16 2012 132 141
41. M.J. Smanski, R.M. Peterson, R.R. Rajski, and B. Shen Engineered Streptomyces platensis strains that overproduce antibiotic platensimycin and platencin Antimicrobial Agents and Chemotherapy 53 2009 1299 1304
42. M.J. Smanski, Z. Yu, J. Casper, S. Lin, R.M. Peterson, and Y. Chen Dedicated ent-kaurene and ent-atiserene synthases for platensimycin and platencin biosynthesis Proceedings of the National Academy of Sciences of the United States of America 108 2011 13498 13503
43. C.L. Steele, J. Crock, J. Bohlman, and R. Croteau Sesquiterpene synthases from Grand Fir (Abies grandis) The Journal of Biological Chemistry 273 1998 2078 2089
44. L.C. Tarshis, P.J. Proteau, B.A. Kellogg, C. Sacchettini, and C.D. Poulter Regulation of product chain length by isoprenyl diphosphate synthases Proceedings of the National Academy of Sciences of the United States of America 93 1996 15018 15023 (Pubitemid 27009544)
45. T. Toyomasu, R. Niida, H. Kenmoku, Y. Kanno, S. Miura, and C. Nakano Identification of diterpene biosynthetic gene clusters and functional analysis of labdane-related diterpene cyclases in Phomopsis amygdali Bioscience, Biotechnology, and Biochemistry 72 2008 1038 1047 (Pubitemid 351679351)
46. B. Tudzynski Gibberellin biosynthesis in fungi: Genes, enzymes, evolution, and impact on biotechnology Applied Microbiology and Biotechnology 66 2005 597 611 (Pubitemid 40385622)
47. J. Wang, S. Kodali, S.H. Lee, A. Galgoci, R. Painter, and K. Dorso Discovery of platencin, a dual FabF and FabH inhibitor with in vivo antibiotic properties Proceedings of the National Academy of Sciences of the United States of America 104 2007 7612 7616 (Pubitemid 47185954)
48. J. Wang, S.M. Soisson, K. Young, W. Shoop, S. Kodali, and A. Galgoci Platensimycin is a selective FabF inhibitor with potent antibiotic properties Nature 441 2006 358 361 (Pubitemid 44050201)
49. M. Xu, M.L. Hillwig, S. Prisic, R.M. Coates, and R.J. Peters Functional identification of rice syn-copalyl diphosphate synthase and its role in initiating biosynthesis of diterpenoid phytoalexin/allelopathic natural products The Plant Journal 39 2004 309 318 (Pubitemid 39040137)
50. D. Yang, X. Zhu, X. Wu, Z. Feng, L. Huang, and B. Shen Titer improvement of iso-migrastatin in selected heterologous Streptomyces hosts and related analysis of mRNA expression by quantitative RT-PCR Applied Microbiology and Biotechnology 89 2011 1709 1719
51. Y. Yoshikuni, T.E. Ferrin, and J.D. Keasling Designed divergent evolution of enzyme function Nature 440 2006 1078 1082
52. Z. Yu, M.J. Smanski, R.M. Peterson, K. Marchillo, D. Andes, and S.R. Rajski Engineering of Streptomyces platensis MA7339 for overproduction of platencin and congeners Organic Letters 12 2010 1744 1747