Cleavage of four carbon-carbon bonds during biosynthesis of the griseorhodin a spiroketal pharmacophore

Journal of the American Chemical Society

Volumn 131, Issue 6, 2009, Pages 2297-2305

  Yunt, Zeynep ^a   Reinhardt, Kathrin ^a   Li, Aiying ^b,e   Engeser, Marianne ^a   Dahse, Hans Martin ^c   Gütschow, Michael ^a   Bruhn, Torsten ^d   Bringmann, Gerhard ^d   Piel, Jörn ^a  

^a UNIVERSITY OF BONN   (Germany)

^b MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

^c HANS KNÖLL INSTITUTE   (Germany)

^d UNIVERSITY OF WÜRZBURG   (Germany)

^e CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; BIOCHEMICAL ENGINEERING; BIOCHEMISTRY; BIOSYNTHESIS; CELL MEMBRANES; DICHROISM; ENZYMES;

ABSOLUTE CONFIGURATION; BIOSYNTHETIC GENE CLUSTER; BIOSYNTHETIC INCORPORATION; CARBON-CARBON BOND; CD MEASUREMENTS; CIRCULAR DICHROISM; CYTOTOXIC; DELETION VARIANTS; ELASTASE; HELIQUINOMYCIN; HETEROLOGOUS EXPRESSION; HIV REVERSE TRANSCRIPTASE; HUMAN TELOMERASE; METABOLIC ANALYSIS; OXIDOREDUCTASE; PHARMACOPHORE; POLYKETIDE; POLYKETIDE STRUCTURE; POLYKETIDES; STREPTOMYCES SP; TELOMERASE; UBIQUINONE;

PHARMACODYNAMICS;

ANTIINFECTIVE AGENT; CARBON; COLLINONE; CYTOCHROME P450; CYTOTOXIC AGENT; DIDEOXYGRISEORHODIN C; GRISEORHODIN A; LENTICULONE; LEUKOCYTE ELASTASE INHIBITOR; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG; GRISEORHODINS; NAPHTHOQUINONE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE);

ANTIBACTERIAL ACTIVITY; ARTICLE; CATALYSIS; CHEMICAL BOND; CIRCULAR DICHROISM; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SYNTHESIS; ENZYME INHIBITION; EPOXIDATION; GENE CLUSTER; GENE DELETION; GENE EXPRESSION; GENETIC VARIABILITY; NONHUMAN; NUCLEOTIDE SEQUENCE; PHARMACOPHORE; QUANTUM CHEMISTRY; STREPTOMYCES; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; ENZYMOLOGY; GENETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; MOLECULAR GENETICS; MULTIGENE FAMILY;

BASE SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; MOLECULAR SEQUENCE DATA; MULTIGENE FAMILY; NAPHTHOQUINONES; QUINONE REDUCTASES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STREPTOMYCES;

EID: 67849104143     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja807827k     Document Type: Article

References (49)

1. Brasholz, M.; Sorgel, S.; Azap, C.; Reissig, H. U. Eur. J. Org. Chem. 2007, 3801-3814.
2. Puder, C.; Loya, S.; Hizi, A.; Zeeck, A. Eur. J. Org. Chem. 2000, 729-735.
3. Chino, M.; Nishikawa, K.; Tsuchida, T.; Sawa, R.; Nakamura, H.; Nakamura, K. T.; Muraoka, Y.; Ikeda, D.; Naganawa, H.; Sawa, T.; Takeuchi, T. J. Antibiot. 1997, 50, 143-146.
4. Goldman, M. E.; Salituro, G. S.; Bowen, J. A.; Williamson, J. M.; Zink, D. L.; Schleif, W. A.; Emini, E. A. Mol. Pharmacol. 1990, 38, 20-25.
5. Ueno, T.; Takahashi, H.; Oda, M.; Mizunuma, M.; Yokoyama, A.; Goto, Y.; Mizushina, Y.; Sakaguchi, K.; Hayashi, H. Biochemistry 2000, 39, 5995-6002.
6. Chumsri, S.; Burger, A. M. Curr. Opin. Mol. Ther. 2008, 10, 323-333.
7. Rezler, E. M.; Bearss, D. J.; Hurley, L. H. Annu. Rev. Pharmacol. Toxicol. 2003, 43, 359-379.
8. Rix, U.; Fischer, C.; Remsing, L. L.; Rohr, J. Nat. Prod. Rep. 2002, 19, 542-580.
9. Li, A. Y.; Piel, J. Chem. Biol. 2002, 9, 1017-1026.
10. Lackner, G.; Schenk, A.; Xu, Z.; Reinhardt, K.; Yunt, Z. S.; Piel, J.; Hertweck, C. J. Am. Chem. Soc. 2007, 129, 9306-9312.
11. Martin, R.; Sterner, O.; Alvarez, M. A.; de Clercq, E.; Bailey, J. E.; Minas, W. J. Antibiot. 2001, 54, 239-249.
12. Hertweck, C.; Luzhetskyy, A.; Rebets, Y.; Bechthold, A. Nat. Prod. Rep. 2007, 24, 162-190.
13. Chater, K. F.; Wilde, L. C. J. Gen. Microbiol. 1980, 116, 323-334.
14. Murphy, K. C.; Campellone, K. G.; Poteete, A. R. Gene 2000, 246, 321-330.
15. Datsenko, K. A.; Wanner, B. L. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 6640-6645.
16. Suetsuna, K.; Osajima, Y. Agric. Biol. Chem. 1989, 53, 241-242.
17. Riveros-Rosas, H.; Julian-Sanchez, A.; Villalobos-Molina, R.; Pardo, J. P.; Pina, E. Eur. J. Biochem. 2003, 270, 3309-3334.
18. Taguchi, T.; Itou, K.; Ebizuka, Y.; Malpartida, F.; Hopwood, D. A.; Surti, C. M.; Booker-Milburn, K. I.; Stephenson, G. R.; Ichinose, K. J. Antibiot. 2000, 53, 144-152.
19. Ichinose, K.; Ozawa, M.; Itou, K.; Kunieda, K.; Ebizuka, Y. Microbiology 2003, 149, 1633-1645.
20. Guengerich, F. P. Arch. Biochem. Biophys. 2003, 409, 59-71.
21. Grüschow, S.; Sherman, D. H. In Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, Germany, 2006.
22. Shah, S.; Xue, Q.; Tang, L.; Carney, J. R.; Betlach, M.; McDaniel, R. J. Antibiot. 2000, 53, 502-508.
23. He, J.; Müller, M.; Hertweck, C. J. Am. Chem. Soc. 2004, 126, 16742-16743.
24. Gibson, M.; Nur-e-alam, M.; Lipata, F.; Oliveira, M. A.; Rohr, J. J. Am. Chem. Soc. 2005, 127, 17594-17595.
25. Menendez, N.; Nur-e-Alam, M.; Brana, A. F.; Rohr, J.; Salas, A. F.; Mendez, C. Chem. Biol. 2004, 11, 21-32.
26. Mihovilovic, M. D. Curr. Org. Chem. 2006, 10, 1265-1287.
27. Eppink, M. H. M.; Boeren, S. A.; Vervoort, J.; VanBerkel, W. J. H. J. Bacteriol. 1997, 179, 6680-6687.
28. Fraaije, M. W.; Kamerbeek, N. M.; van Berkel, W. J. H.; Janssen, D. B. FEBS Lett. 2002, 518, 43-47.
29. Piel, J.; Wen, G.; Platzer, M.; Hui, D. ChemBioChem 2004, 5, 93-98.
30. Gu, L. C.; Geders, T. W.; Wang, B.; Gerwick, W. H.; Hakansson, K.; Smith, J. L.; Sherman, D. H. Science 2007, 318, 970-974.
31. Vetting, M. W.; de Carvalho, L.; Yu, M.; Hedge, S. S.; Magnet, S.; Roderick, S. L.; Blanchard, J. S. Arch. Biochem. Biophys. 2005, 433, 212-226.
32. Xiang, L.; Kalaitzis, J. A.; Moore, B. S. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 15609-15614.
33. Eckardt, K.; Tresselt, D.; Schonecker, B. Tetrahedron 1979, 35, 1621-1624.
34. Bringmann, G.; Kraus, J.; Schmitt, U.; Puder, C.; Zeeck, A. Eur. J. Org. Chem. 2000, 2729-2734.
35. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
36. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev.B 1988, 37, 785-789.
37. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222.
38. Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; Defrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654-3665.
39. Bringmann, G.; Busemann, S. In Natural Product Analysis: Chromatography, Spectroscopy, Biological Testing; Schreier, P., Herderich, M., Humpf, H.-U., Schwab, W., Eds.; Vieweg: Wiesbaden, Germany, 1998; pp 195-211.
40. For a first review of the determination of absolute configuration by LC-CD in combination with quantum-chemical calculations, see: Bringmann, G.; Gulder, T. A. M.; Reichert, M.; Gulder, T. Chirality 2008, 20, 628-642.
41. It should be kept in mind that the absolute configurations determined in refs 3 and 34 are both correct but that the wrong descriptors were used. Thus, the correct configurations at the spiro center are (S) for heliquinomycin and (R) for γ-rubromycin. In a similar way, the two possible enantiomers of griseorhodin A were given the wrong descriptors at the spiro center in ref 33.
42. Checa, A.; Ortiz, A. R.; de Pascual-Teresa, B.; Gago, F. J. Med. Chem. 1997, 40, 4136-4145.
43. Maliar, T.; Jedinak, A.; Kadrabová, J.; Sturdik, E. Eur. J. Med. Chem. 2004, 39, 241-248.
44. Weir, M. P.; Bethell, S. S.; Cleasby, A.; Campbell, C. J.; Dennis, D. J.; Finch, H.; Jhoti, H.; Mooney, C. J.; Patel, S.; Tang, C. M.; Wonacott, M. A.; Wharton, C. W. Biochemistry 1998, 37, 6645-6657.
45. Chen, Y. H.; Luo, Y. G.; Ju, J. H.; Wendt-Pienkowski, E.; Rajski, S. R.; Shen, B. J. Nat. Prod. 2008, 71, 431-437.
46. Kim, B. C.; Lee, J. M.; Ahn, J. S.; Kim, B. S. J. Microbiol. Biotechnol. 2007, 17, 830-839.
47. Kieser, T.; Bibb, M. J.; Buttner, M. J.; Chater, K. F.; Hopwood, D. A. Practical Steptomyces Genetics; The John Innes Foundation: Norwich, U.K., 2000.
48. Sambrook, J.; Russel, D. W. Molecular Cloning: A Laboratory Manual, 3rd ed.; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 2001.
49. Hillemann, D.; Puhler, A.; Wohlleben, W. Nucleic Acids Res. 1991, 19, 727-731.