Cloning and Heterologous Expression of the Cyclooctatin Biosynthetic Gene Cluster Afford a Diterpene Cyclase and Two P450 Hydroxylases

Chemistry and Biology

Volumn 16, Issue 7, 2009, Pages 736-743

  Kim, Seung Young ^a   Zhao, Ping ^a   Igarashi, Masayuki ^b   Sawa, Ryuichi ^b   Tomita, Takeo ^a   Nishiyama, Makoto ^a   Kuzuyama, Tomohisa ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

Author keywords

CHEMBIO; PROTEINS

Indexed keywords

BICYCLO COMPOUND; CYCLOOCTATIN; CYTOCHROME P450; DITERPENE; ISOMERASE; LYSOPHOSPHOLIPASE;

ARTICLE; DRUG ANTAGONISM; GENETICS; HYDROXYLATION; METABOLISM; METHODOLOGY; MOLECULAR CLONING; MULTIGENE FAMILY; STREPTOMYCES;

BICYCLO COMPOUNDS; CLONING, MOLECULAR; CYTOCHROME P-450 ENZYME SYSTEM; DITERPENES; HYDROXYLATION; INTRAMOLECULAR LYASES; LYSOPHOSPHOLIPASE; METABOLIC NETWORKS AND PATHWAYS; MULTIGENE FAMILY; STREPTOMYCES;

STREPTOMYCES; STREPTOMYCES ALBUS; STREPTOMYCES MELANOSPOROFACIENS;

EID: 67651112019     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2009.06.007     Document Type: Article

References (21)

1. Aoyagi T., Aoyama T., Kojima F., Hattori S., Honma Y., Hamada M., and Takeuchi T. Cyclooctatin, a new inhibitor of lysophospholipase, produced by Streptomyces melanosporofaciens MI614-43F2. Taxonomy, production, isolation, physico-chemical properties and biological activities. J. Antibiot. (Tokyo) 45 (1992) 1587-1591
2. Aoyama T., Naganawa H., Muraoka Y., Aoyagi T., and Takeuchi T. The structure of cyclooctatin, a new inhibitor of lysophospholipase. J. Antibiot. (Tokyo) 45 (1992) 1703-1704
3. Bierman M., Logan R., O'Brien K., Seno E.T., Rao R.N., and Schoner B.E. Plasmid cloning vectors for the conjugal transfer of DNA from Escherichia coli to Streptomyces spp. Gene 116 (1992) 43-49
4. Caruthers J.M., Kang I., Rynkiewicz M.J., Cane D.E., and Christianson D.W. Crystal structure determination of aristolochene synthase from the blue cheese mold, Penicillium roqueforti. J. Biol. Chem. 275 (2000) 25533-25539
5. Christianson D.W. Structural biology and chemistry of the terpenoid cyclases. Chem. Rev. 106 (2006) 3412-3442
6. Corpet F. Multiple sequence alignment with hierarchical clustering. Nucleic Acids Res. 16 (1988) 10881-10890
7. Dairi T., Aisaka K., Katsumata R., and Hasegawa M. A self-defense gene homologous to tetracycline effluxing gene essential for antibiotic production in Streptomyces aureofaciens. Biosci. Biotechnol. Biochem. 59 (1995) 1835-1841
8. Dairi T., Hamano Y., Kuzuyama T., Itoh N., Furihata K., and Seto H. Eubacterial diterpene cyclase genes essential for production of the isoprenoid antibiotic terpentecin. J. Bacteriol. 183 (2001) 6085-6094
9. Davisson V.J., Woodside A.B., and Poulter C.D. Synthesis of allylic and homoallylic isoprenoid pyrophosphates. Methods Enzymol. 110 (1985) 130-144
10. Hamano Y., Kuzuyama T., Itoh N., Furihata K., Seto H., and Dairi T. Functional analysis of eubacterial diterpene cyclases responsible for biosynthesis of a diterpene antibiotic, terpentecin. J. Biol. Chem. 277 (2002) 37098-37104
11. Ishikawa J., and Hotta K. FramePlot: a new implementation of the frame analysis for predicting protein-coding regions in bacterial DNA with a high G + C content. FEMS Microbiol. Lett. 174 (1999) 251-253
12. Jez J.M., Ferrer J.L., Bowman M.E., Dixon R.A., and Noel J.P. Dissection of malonyl-coenzyme A decarboxylation from polyketide formation in the reaction mechanism of a plant polyketide synthase. Biochemistry 39 (2000) 890-902
13. Kawasaki T., Kuzuyama T., Kuwamori Y., Matsuura N., Itoh N., Furihata K., Seto H., and Dairi T. Presence of copalyl diphosphate synthase gene in an actinomycete possessing the mevalonate pathway. J. Antibiot. (Tokyo) 57 (2004) 739-747
14. Kieser T., Bibb M.J., Buttner M.J., Chater K.F., and Hopwood D.A. Practical Streptomyces Genetics (2000), John Innes Foundation, Norwich, UK
15. Lesburg C.A., Zhai G., Cane D.E., and Christianson D.W. Crystal structure of pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in biology. Science 277 (1997) 1820-1824
16. MacMillan J., and Beale M.H. Diterpene biosynthesis. In: Cane D.E. (Ed). Comprehensive Natural Products Chemistry (vol. 2), Isoprenoids Including Carotenoids and Steroids (1999), Elsevier, Amsterdam, Netherlands 217-243
17. Nakano C., Okamura T., Sato T., Dairi T., and Hoshino T. Mycobacterium tuberculosis H37Rv3377c encodes the diterpene cyclase for producing the halimane skeleton. Chem. Commun. (Camb.) 8 (2005) 1016-1018
18. Poirot O., O'Toole E., and Notredame C. Tcoffee@igs: A web server for computing, evaluating and combining multiple sequence alignments. Nucleic Acids Res. 31 (2003) 3503-3506
19. Shishova E.Y., Di Costanzo L., Cane D.E., and Christianson D.W. X-ray crystal structure of aristolochene synthase from Aspergillus terreus and evolution of templates for the cyclization of farnesyl diphosphate. Biochemistry 46 (2007) 1941-1951
20. Starks C.M., Back K., Chappell J., and Noel J.P. Structural basis for cyclic terpene biosynthesis by tobacco 5-epi-aristolochene synthase. Science 277 (1997) 1815-1820
21. Toyomasu T., Tsukahara M., Kaneko A., Niida R., Mitsuhashi W., Dairi T., Kato N., and Sassa T. Fusicoccins are biosynthesized by an unusual chimera diterpene synthase in fungi. Proc. Natl. Acad. Sci. USA 104 (2007) 3084-3088