Combinatorial generation of complexity by redox enzymes in the chaetoglobosin A biosynthesis

Journal of the American Chemical Society

Volumn 135, Issue 19, 2013, Pages 7371-7377

  Ishiuchi, Kan'Ichiro ^a   Nakazawa, Takehito ^a   Yagishita, Fumitoshi ^b   Mino, Takashi ^b   Noguchi, Hiroshi ^a   Hotta, Kinya ^c   Watanabe, Kenji ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b CHIBA UNIVERSITY   (Japan)

^c UNIVERSITY OF NOTTINGHAM MALAYSIA CAMPUS   (Malaysia)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; CHAETOMIUM GLOBOSUM; COMBINATORIAL GENERATIONS; HETEROLOGOUS EXPRESSION; INTERMEDIATE COMPOUND; NATURAL PRODUCTS; STRUCTURAL COMPLEXITY; X RAY CRYSTAL STRUCTURES;

BIOCHEMISTRY; BIOSYNTHESIS; COMPLEX NETWORKS; ENZYMES; GENE EXPRESSION; OXIDATION; POLYPEPTIDES; SCAFFOLDS; YEAST;

REACTION INTERMEDIATES;

CHAETOGLOBOSIN A ENZYME; CYTOCHROME P450; FUNGAL ENZYME; PEPTIDE SYNTHASE; POLYKETIDE SYNTHASE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ARTICLE; BIOSYNTHESIS; BIOTRANSFORMATION; CHAETOMIUM; CHAETOMIUM GLOBOSUM; COMBINATORIAL CHEMISTRY; CRYSTAL STRUCTURE; ENZYME SYNTHESIS; FUNGAL STRAIN; GENE EXPRESSION; IN VIVO STUDY; NONHUMAN; OXIDATION REDUCTION REACTION; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY;

BIOSYNTHETIC PATHWAYS; CHAETOMIUM; GENE DELETION; GENES, FUNGAL; INDOLE ALKALOIDS; LIGASES; MIXED FUNCTION OXYGENASES; OXIDATION-REDUCTION; OXIDOREDUCTASES;

EID: 84877826871     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja402828w     Document Type: Article

References (33)

1. Sekita, S.; Yoshihira, K.; Natori, S.; Kuwano, H. Tetrahedron Lett. 1973, 2109-2112
2. Sekita, S.; Yoshihira, K.; Natori, S.; Kuwano, H. Chem. Pharm. Bull. 1982, 30, 1629-1638
3. Silverton, J. V.; Akiyama, T.; Kabuto, C.; Sekita, S.; Yoshihira, K.; Natori, S. Tetrahedron Lett. 1976, 1349-1350
4. Scherlach, K.; Boettger, D.; Remme, N.; Hertweck, C. Nat. Prod. Rep. 2010, 27, 869-886
5. Low, I.; Jahn, W.; Wieland, T.; Sekita, S.; Yoshihira, K.; Natori, S. Anal. Biochem. 1979, 95, 14-18
6. Galagan, J. E.; Calvo, S. E.; Cuomo, C.; Ma, L. J.; Wortman, J. R.; Batzoglou, S.; Lee, S. I.; Bastürkmen, M.; Spevak, C. C.; Clutterbuck, J.; Kapitonov, V.; Jurka, J.; Scazzocchio, C.; Farman, M.; Butler, J.; Purcell, S.; Harris, S.; Braus, G. H.; Draht, O.; Busch, S.; D'Enfert, C.; Bouchier, C.; Goldman, G. H.; Bell-Pedersen, D.; Griffiths-Jones, S.; Doonan, J. H.; Yu, J.; Vienken, K.; Pain, A.; Freitag, M.; Selker, E. U.; Archer, D. B.; Penalva, M. A.; Oakley, B. R.; Momany, M.; Tanaka, T.; Kumagai, T.; Asai, K.; Machida, M.; Nierman, W. C.; Denning, D. W.; Caddick, M.; Hynes, M.; Paoletti, M.; Fischer, R.; Miller, B.; Dyer, P.; Sachs, M. S.; Osmani, S. A.; Birren, B. W. Nature 2005, 438, 1105-1115
7. Keller, N. P.; Turner, G.; Bennett, J. W. Nat. Rev. Microbiol. 2005, 3, 937-947
8. Schümann, J.; Hertweck, C. J. Am. Chem. Soc. 2007, 129, 9564-9565
9. Sims, J. W.; Schmidt, E. W. J. Am. Chem. Soc. 2008, 130, 11149-11155
10. Liu, X.; Walsh, C. T. Biochemistry 2009, 48, 8746-8757
11. Boettger, D.; Hertweck, C. ChemBioChem 2013, 14, 28-42
12. Kennedy, J.; Auclair, K.; Kendrew, S. G.; Park, C.; Vederas, J. C.; Hutchinson, C. R. Science 1999, 284, 1368-1372
13. Watanabe, K.; Mie, T.; Ichihara, A.; Oikawa, H.; Honma, M. J. Biol. Chem. 2000, 275, 38393-38401
14. Ose, T.; Watanabe, K.; Mie, T.; Honma, M.; Watanabe, H.; Yao, M.; Oikawa, H.; Tanaka, I. Nature 2003, 422, 185-189
15. Ma, S. M.; Li, J. W. H.; Choi, J. W.; Zhou, H.; Lee, K. K. M.; Moorthie, V. A.; Xie, X.; Kealey, J. T.; Da Silva, N. A.; Vederas, J. C.; Tang, Y. Science 2009, 326, 589-592
16. Oikawa, H.; Murakami, Y.; Ichihara, A. Tetrahedron Lett. 1991, 32, 4533-4536
17. Oikawa, H.; Murakami, Y.; Ichihara, A. J. Chem. Soc. Perkin Trans. 1 1992, 2949-2953
18. Oikawa, H.; Murakami, Y.; Ichihara, A. Biosci. Biotech. Biochem. 1993, 57, 628-631
19. Cui, C. M.; Li, X. M.; Li, C. S.; Proksch, P.; Wang, B. G. J. Nat. Prod. 2010, 73, 729-733
20. Wei, Y. F.; Robins, P.; Carter, K.; Caldecott, K.; Pappin, D. J.; Yu, G. L.; Wang, R. P.; Shell, B. K.; Nash, R. A.; Schär, P.; Barnes, D. E.; Haseltine, W. A.; Lindahl, T. Mol. Cell. Biol. 1995, 15, 3206-3216
21. Ishibashi, K.; Suzuki, K.; Takakura, C.; Inoue, H. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 14871-14876
22. Nakazawa, T.; Ishiuchi, K.; Sato, M.; Tsunematsu, T.; Sugimoto, S.; Gotanda, Y.; Noguchi, H.; Hotta, K.; Watanabe, K., manuscript submitted.
23. Johnson, M.; Zaretskaya, I.; Raytselis, Y.; Merezhuk, Y.; McGinnis, S.; Madden, T. L. Nucleic Acids Res. 2008, 36, W5-9
24. Qiao, K.; Chooi, Y. H.; Tang, Y. Metab. Eng. 2011, 13, 723-732
25. Bergmann, S.; Schümann, J.; Scherlach, K.; Lange, C.; Brakhage, A. A.; Hertweck, C. Nat. Chem. Biol. 2007, 3, 213-217
26. Brown, D. W.; Adams, T. H.; Keller, N. P. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 14873-14877
27. Bok, J. W.; Hoffmeister, D.; Maggio-Hall, L. A.; Murillo, R.; Glasner, J. D.; Keller, N. P. Chem. Biol. 2006, 13, 31-37
28. Bok, J. W.; Chiang, Y. M.; Szewczyk, E.; Reyes-Dominguez, Y.; Davidson, A. D.; Sanchez, J. F.; Lo, H. C.; Watanabe, K.; Strauss, J.; Oakley, B. R.; Wang, C. C. C.; Keller, N. P. Nat. Chem. Biol. 2009, 5, 462-464
29. Chiang, Y. M.; Szewczyk, E.; Davidson, A. D.; Keller, N.; Oakley, B. R.; Wang, C. C. C. J. Am. Chem. Soc. 2009, 131, 2965-2970
30. Marchler-Bauer, A.; Bryant, S. H. Nucleic Acids Res. 2004, 32, W327-331
31. Gardiner, D. M.; Howlett, B. J. FEMS Microbiol. Lett. 2005, 248, 241-248
32. Wang, P.; Gao, X.; Tang, Y. Curr. Opin. Chem. Biol. 2012, 16, 362-369
33. Zolan, M. E.; Pukkila, P. J. Mol. Cell. Biol. 1986, 6, 195-200