Baeyer-villiger C-C bond cleavage reaction in gilvocarcin and jadomycin biosynthesis

Journal of the American Chemical Society

Volumn 134, Issue 44, 2012, Pages 18181-18184

  Tibrewal, Nidhi ^a   Pahari, Pallab ^a,b   Wang, Guojun ^a   Kharel, Madan K ^a   Morris, Caleb ^a   Downey, Theresa ^a   Hou, Yanpeng ^c   Bugni, Tim S ^c   Rohr, Jürgen ^a  

^a University of Kentucky   (United States)

^b CSIR NORTH EAST INSTITUTE OF SCIENCE AND TECHNOLOGY   (India)

^c UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BAEYER-VILLIGER; BENZ[A]ANTHRACENE; C-C BONDS; CLEAVAGE MECHANISM; KEY ENZYMES;

ENZYMES;

BIOCHEMISTRY;

ACETIC ACID; ANTIBIOTIC AGENT; ANTINEOPLASTIC AGENT; CARBON; DEFUCOGILVOCARCIN M; GILVOCARCIN; JADOMYCIN; MALONIC ACID; NATURAL PRODUCT; POLYKETIDE SYNTHASE; PROPIONIC ACID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOSYNTHESIS; CHEMICAL BOND; NONHUMAN; STREPTOMYCES;

ANTIBIOTICS, ANTINEOPLASTIC; COUMARINS; GLYCOSIDES; ISOQUINOLINES; NAPHTHOQUINONES; STREPTOMYCES;

EID: 84868568903     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3081154     Document Type: Article

References (22)

1. Fischer, C.; Lipata, F.; Rohr, J. J. Am. Chem. Soc. 2003, 125, 7818
2. Nakano, H.; Matsuda, Y.; Ito, K.; Ohkubo, S.; Morimoto, M.; Tomita, F. J. Antibiot. 1981, 34, 266
3. Matsumoto, A.; Fujiwara, Y.; Elespuru, R. K.; Hanawalt, P. C. Photochem. Photobiol. 1994, 60, 225
4. Matsumoto, A.; Hanawalt, P. C. Cancer Res. 2000, 60, 3921
5. McGee, L. R.; Misra, R. J. Am. Chem. Soc. 1990, 112, 2386
6. Shepherd, M. D.; Kharel, M. K.; Zhu, L. L.; Van Lanen, S. G.; Rohr, J. Org. Biomol. Chem. 2010, 8, 3851
7. Pahari, P.; Kharel, M. K.; Shepherd, M. D.; Van Lanen, S. G.; Rohr, J. Angew. Chem., Int. Ed. 2012, 51, 1216
8. Tibrewal, N.; Downey, T. E.; Van Lanen, S. G.; Ul Sharif, E.; O'Doherty, G. A.; Rohr, J. J. Am. Chem. Soc. 2012, 134, 12402
9. Kharel, M. K.; Zhu, L. L.; Liu, T.; Rohr, J. J. Am. Chem. Soc. 2007, 129, 3780
10. Kharel, M. K.; Pahari, P.; Lian, H.; Rohr, J. ChemBioChem 2009, 10, 1305
11. Widboom, P. F.; Fielding, E. N.; Liu, Y.; Bruner, S. D. Nature 2007, 447, 342
12. Chen, Y.; Fan, K.; He, Y.; Xu, X.; Peng, Y.; Yu, T.; Jia, C.; Yang, K. ChemBioChem 2010, 11, 1055
13. Kharel, M. K.; Rohr, J. Curr. Opin. Chem. Biol. 2012, 16, 150
14. Shen, B.; Hutchinson, C. R. Biochemistry 1993, 32, 6656
15. Chung, J. Y.; Fuji, I.; Harada, S.; Sankawa, U.; Ebizuka, Y. J. Bacteriol. 2002, 184, 6155
16. Shan, M. D.; Sharif, E. U.; O'Doherty, G. A. Angew. Chem., Int. Ed. 2010, 49, 9492
17. Leisch, H.; Morley, K.; Lau, P. C. Chem. Rev. 2011, 111, 4165
18. Jiang, J.; Tetzlaff, C. N.; Talamatsu, S.; Iwatsuki, M.; Komatsu, M.; Ikeda, H.; Cane, D. E. Biochemistry 2009, 48, 6431
19. Beam, M. P.; Bosserman, M. A.; Noinaj, N.; Wehenkel, M.; Rohr, J. Biochemistry 2009, 48, 4476
20. Sasaki, E.; Ogasawara, Y.; Liu, H.-w. J. Am. Chem. Soc. 2010, 132, 7405
21. Minto, R. E.; Townsend, C. A. Chem. Rev. 1997, 97, 2537
22. Philmus, B.; Abdelwahed, S.; Williams, H. J.; Fenwick, M. K.; Ealick, S. E.; Begley, T. P. J. Am. Chem. Soc. 2012, 134, 5326