Coupling Reaction of Indolepyruvic Acid by StaD and Its Product: Implications for Biosynthesis of Indolocarbazole and Violacein

ChemBioChem

Volumn 13, Issue 17, 2012, Pages 2495-2500

  Asamizu, Shumpei ^a   Hirano, Satoshi ^b   Onaka, Hiroyasu ^a,c   Koshino, Hiroyuki ^d   Shiro, Yoshitsugu ^b   Nagano, Shingo ^e  

^a TOYAMA PREFECTURAL UNIVERSITY   (Japan)

^b RIKEN SPring 8 Center ^*  (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

^d RIKEN   (Japan)

^e TOTTORI UNIVERSITY   (Japan)

Author keywords

Biosynthesis; CC coupling; Heme proteins; Indolocarbazoles; Staurosporine

Indexed keywords

AMMONIA; CARBAZOLE DERIVATIVE; HEMOPROTEIN; HETEROCYCLIC COMPOUND; INDOLEPYRUVIC ACID; STAD ENZYME; UNCLASSIFIED DRUG; VIOLACEIN;

ARTICLE; BIOSYNTHESIS; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; DIMERIZATION; EXPRESSION VECTOR; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN PURIFICATION; PROTON NUCLEAR MAGNETIC RESONANCE;

BIOCATALYSIS; CARBAZOLES; HEMEPROTEINS; INDOLES;

EID: 84869385385     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201200535     Document Type: Article

References (27)

1. C. Sánchez, C. Mendez, J. A. Salas, Nat. Prod. Rep. 2006, 23, 1007.
2. H. Nakano, S. Omura, J. Antibiot. 2009, 62, 17.
3. C. Sánchez, I. A. Butovich, A. F. Brana, J. Rohr, C. Mendez, J. A. Salas, Chem. Biol. 2002, 9, 519.
4. H. Onaka, S. Taniguchi, Y. Igarashi, T. Furumai, J. Antibiot. 2002, 55, 1063.
5. S. Asamizu, Y. Kato, Y. Igarashi, T. Furumai, H. Onaka, Tetrahedron Lett. 2006, 47, 473.
6. R. Fröde, C. Hinze, I. Josten, B. Schmidt, B. Steffan, W. Steglich, Tetrahedron Lett. 1994, 35, 1689.
7. C. Paal, Chem. Ber. 1884, 17, 2756.
8. L. Knorr, Chem. Ber. 1884, 17, 2863.
9. A. R. Howard-Jones, C. T. Walsh, J. Am. Chem. Soc. 2006, 128, 12289.
10. M. Makino, H. Sugimoto, Y. Shiro, S. Asamizu, H. Onaka, S. Nagano, Proc. Natl. Acad. Sci. USA 2007, 104, 11591.
11. S. Asamizu, Y. Shiro, Y. Igarashi, S. Nagano, H. Onaka, Biosci. Biotechnol. Biochem. 2011, 75, 2184.
12. T. Nishizawa, C. C. Aldrich, D. H. Sherman, J. Bacteriol. 2005, 187, 2084.
13. T. Nishizawa, S. Gruschow, D. H. Jayamaha, C. Nishizawa-Harada, D. H. Sherman, J. Am. Chem. Soc. 2006, 128, 724.
14. H. Onaka, S. Taniguchi, Y. Igarashi, T. Furumai, Biosci. Biotechnol. Biochem. 2003, 67, 127.
15. Q. Gao, C. Zhang, S. Blanchard, J. S. Thorson, Chem. Biol. 2006, 13, 733.
16. K. S. Ryan, A. R. Howard-Jones, M. J. Hamill, S. J. Elliott, C. T. Walsh, C. L. Drennan, Proc. Natl. Acad. Sci. USA 2007, 104, 15311.
17. S. Y. Kim, J. S. Park, C. S. Chae, C. G. Hyun, B. W. Choi, J. Shin, K. B. Oh, Appl. Microbiol. Biotechnol. 2007, 75, 1119.
18. A. Z. Momen, T. Hoshino, Biosci. Biotechnol. Biochem. 2000, 64, 539.
19. A. R. Howard-Jones, C. T. Walsh, Biochemistry 2005, 44, 15652.
20. C. Sánchez, A. F. Brana, C. Mendez, J. A. Salas, ChemBioChem 2006, 7, 1231.
21. C. J. Balibar, C. T. Walsh, Biochemistry 2006, 45, 15444.
22. S. Asamizu, Y. Kato, Y. Igarashi, H. Onaka, Tetrahedron Lett. 2007, 48, 2923.
23. K. Shinoda, T. Hasegawa, H. Sato, M. Shinozaki, H. Kuramoto, Y. Takamiya, T. Sato, N. Nikaidou, T. Watanabe, T. Hoshino, Chem. Commun. 2007, 4140.
24. H. B. Dunford, Heme Peroxidases, Wiley-VCH, New York, 1999.
25. H. Agematu, K. Suzuki, H. Tsuya, Biosci. Biotechnol. Biochem. 2011, 75, 2008.
26. S. F. Brady, C. J. Chao, J. Handelsman, J. Clardy, Org. Lett. 2001, 3, 1981.
27. S. Hakvåg, E. Fjaervik, G. Klinkenberg, S. E. Borgos, K. D. Josefsen, T. E. Ellingsen, S. B. Zotchev, Mar. Drugs 2009, 7, 576.