Resin Acid Conversion with CYP105A1: An Enzyme with Potential for the Production of Pharmaceutically Relevant Diterpenoids

ChemBioChem

Volumn 14, Issue 4, 2013, Pages 467-473

  Janocha, Simon ^a   Zapp, Josef ^a   Hutter, Michael ^a   Kleser, Michael ^a   Bohlmann, Jörg ^b   Bernhardt, Rita ^a  

^a SAARLAND UNIVERSITY   (Germany)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

15 hydroxyabietic acid; Biocatalysis; Cytochromes P450; Hydroxylation; Terpenoids

Indexed keywords

15 HYDROXYABIETIC ACID; 15 HYDROXYDEHYDROABIETIC ACID; 15,16 EPOXYISOPIMARIC ACID; ABIETIC ACID; CYTOCHROME P450; CYTOCHROME P450 105A1; DEHYDROABIETIC ACID; DITERPENOID; ISOPIMARIC ACID; LEVOPIMARIC ACID; PALUSTRIC ACID; PIMARIC ACID; RESIN; SANDARACOPIMARIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BIOTECHNOLOGY; CATALYSIS; DRUG METABOLISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STREPTOMYCES; STREPTOMYCES GRISEOLUS;

BACTERIAL PROTEINS; CATALYTIC DOMAIN; CYTOCHROME P-450 ENZYME SYSTEM; DITERPENES; DITERPENES, ABIETANE; INDUSTRIAL MICROBIOLOGY; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR DOCKING SIMULATION; STREPTOMYCES GRISEUS;

EID: 84874393098     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201200729     Document Type: Article

References (40)

1. N. B. Jensen, M. Zagrobelny, K. Hjernø, C. E. Olsen, J. Houghton-Larsen, J. Borch, B. L. Møller, S. Bak, Nat. Commun. 2011, 2, 273.
2. R. Bernhardt, J. Biotechnol. 2006, 124, 128-145.
3. K. S. Rabe, V. J. Gandubert, M. Spengler, M. Erkelenz, C. M. Niemeyer, Anal. Bioanal. Chem. 2008, 392, 1059-1073.
4. T. Kieser, M. J. Bibb, M. J. Buttner, K. F. Chater, D. A. Hopwood, Practical Streptomyces Genetics, 2nd ed., John Innes Foundation, Norwich, 2000.
5. S. D. Bentley, K. F. Chater, A.-M. Cerdeño-Tárraga, G. L. Challis, N. R. Thomson, K. D. James, D. E. Harris, M. A. Quail, H. Kieser, D. Harper, A. Bateman, S. Brown, G. Chandra, C. W. Chen, M. Collins, A. Cronin, A. Fraser, A. Goble, J. Hidalgo, T. Hornsby et al., Nature 2002, 417, 141-147.
6. D. C. Lamb, H. Ikeda, D. R. Nelson, J. Ishikawa, T. Skaug, C. Jackson, S. Omura, M. R. Waterman, S. L. Kelly, Biochem. Biophys. Res. Commun. 2003, 307, 610-619.
7. M. K. Julsing, S. Cornelissen, B. Bühler, A. Schmid, Curr. Opin. Chem. Biol. 2008, 12, 177-186.
8. J.-W. Park, J.-K. Lee, T.-J. Kwon, D.-H. Yi, Y.-J. Kim, S.-H. Moon, H.-H. Suh, S.-M. Kang, Y.-I. Park, Biotechnol. Lett. 2003, 25, 1827-1831.
9. J. A. Romesser, D. P. O'Keefe, Biochem. Biophys. Res. Commun. 1986, 140, 650-659.
10. H. Sugimoto, R. Shinkyo, K. Hayashi, S. Yoneda, M. Yamada, M. Kamakura, S. Ikushiro, Y. Shiro, T. Sakaki, Biochemistry 2008, 47, 4017-4027.
11. N. Sawada, T. Sakaki, S. Yoneda, T. Kusudo, R. Shinkyo, M. Ohta, K. Inouye, Biochem. Biophys. Res. Commun. 2004, 320, 156-164.
12. A. Çelik, S. L. Flitsch, N. J. Turner, Org. Biomol. Chem. 2005, 3, 2930-2934.
13. M. Kleser, F. Hannemann, M. Hutter, J. Zapp, R. Bernhardt, J. Biotechnol. 2012, 157, 405-412.
14. B. Hamberger, T. Ohnishi, B. Hamberger, A. Séguin, J. Bohlmann, Plant Physiol. 2011, 157, 1677-1695.
15. C. I. Keeling, J. Bohlmann, Phytochemistry 2006, 67, 2415-2423.
16. H. Ohtsu, R. Tanak, Y. In, S. Matsunaga, H. Tokuda, H. Nishino, Planta Med. 2001, 67, 55-60.
17. S. S. Feio, S. Franca, A. M. Silva, B. Gigante, J. C. Roseiro, M. J. M. Curto, J. Appl. Microbiol. 2002, 93, 765-771.
18. B. Gigante, C. Santos, A. M. Silva, M. J. M. Curto, M. S. J. Nascimento, E. Pinto, M. Pedro, F. Cerqueira, M. M. Pinto, M. P. Duarte, A. Laires, J. Rueff, J. Gonçalves, M. I. Pegado, M. L. Valdeira, Bioorg. Med. Chem. 2003, 11, 1631-1638.
19. A. T. Karlberg, K. Bohlinder, A. Boman, U. Hacksell, J. Hermansson, S. Jacobsson, J. L. Nilsson, J. Pharm. Pharmacol. 1988, 40, 42-47.
20. J. M. Leach, A. N. Thakore, Prog. Water Technol. 1977, 9, 787-798.
21. F. Hannemann, A. Bichet, K. M. Ewen, R. Bernhardt, Biochim. Biophys. Acta Gen. Subj. 2007, 1770, 330-344.
22. C. R. Jefcoate, Methods Enzymol. 1978, 52, 258-279.
23. J. B. Schenkman, I. Jansson in Methods in Molecular Biology, Vol. 107 (Eds: I. R. Phillips, E. A. Shephard), Humana Press, Totowa, 1998, pp. 25-33.
24. S. Bleif, F. Hannemann, M. Lisurek, J. P. von Kries, J. Zapp, M. Dietzen, I. Antes, R. Bernhardt, ChemBioChem 2011, 12, 576-582.
25. K. Hayashi, H. Sugimoto, R. Shinkyo, M. Yamada, S. Ikeda, S. Ikushiro, M. Kamakura, Y. Shiro, T. Sakaki, Biochemistry 2008, 47, 11964-11972.
26. R. Huey, G. M. Morris, A. J. Olson, D. S. Goodsell, J. Comput. Chem. 2007, 28, 1145-1152.
27. G. M. Morris, D. S. Goodsell, R. S. Halliday, R. Huey, W. E. Hart, R. K. Belew, A. J. Olson, J. Comput. Chem. 1998, 19, 1639-1662.
28. V. B. Urlacher, M. Girhard, Trends Biotechnol. 2012, 30, 26-36.
29. Y. Yasutake, N. Imoto, Y. Fujii, T. Fujii, A. Arisawa, T. Tamura, Biochem. Biophys. Res. Commun. 2007, 361, 876-882.
30. A. M. Downs, J. E. Sansom, Contact Dermatitis 1999, 41, 305-310.
31. B. Arreguy-San Miguel, M. Taran, P. Picard, B. Delmond, Synth. Commun. 1989, 19, 979-986.
32. Y, Imaizumi, K. Sakamoto, A. Yamada, A. Hotta, S. Ohya, K. Muraki, M. Uchiyama, T. Ohwada, Mol. Pharmacol. 2002, 62, 836-846.
33. T. Omura, R. Sato, J. Biol. Chem. 1964, 239, 2370-2378.
34. K. M. Ewen, B. Schiffler, H. Uhlmann-Schiffler, R. Bernhardt, F. Hannemann, FEMS Yeast Res. 2008, 8, 432-441.
35. B. Schiffler, M. Bureik, W. Reinle, E.-C. Müller, F. Hannemann, R. Bernhardt, J. Inorg. Biochem. 2004, 98, 1229-1237.
36. J. W. Williams, J. F. Morrison, Methods Enzymol. 1979, 63, 437-467.
37. M. F. Sanner, J. Mol. Graphics Modell. 1999, 17, 57-61.
38. L. Haberkorn, V. Mutterer, E. Gimenez Arnau, J.-P. Lepoittevin, Synlett 2001, 2001, 1723-1726.
39. K. Krohn, E. Budianto, U. Floerke, B. M. Hausen, Liebigs Ann. Chem. 1992, 911-919.
40. A. Abad, M. Arno, L. R. Domingo, R. J. Zaragoza, Tetrahedron 1985, 41, 4937-4940.