Understanding Programming of Fungal Iterative Polyketide Synthases: The Biochemical Basis for Regioselectivity by the Methyltransferase Domain in the Lovastatin Megasynthase

Journal of the American Chemical Society

Volumn 137, Issue 50, 2015, Pages 15688-15691

  Cacho, Ralph A ^a   Thuss, Justin ^b   Xu, Wei ^a   Sanichar, Randy ^b   Gao, Zhizeng ^b   Nguyen, Allison ^a   Vederas, John C ^b   Tang, Yi ^a  

^a University of California   (United States)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CHAINS; KETONES;

FUNCTIONALIZATIONS; ITERATIVE FASHION; METHYLTRANSFERASES; NATURAL PRODUCTS; POLYKETIDE SYNTHASES; SELECTIVE MODIFICATION; STRUCTURAL DIVERSITY; SUBSTRATE SPECIFICITY;

SUBSTRATES;

FUNGAL ENZYME; LOVB SYNTHETASE; METHYLTRANSFERASE; POLYKETIDE SYNTHASE; SYNTHETASE; UNCLASSIFIED DRUG; MEVINOLIN;

ARTICLE; BIOCHEMISTRY; ENZYME KINETICS; ENZYME MODIFICATION; ENZYME SPECIFICITY; ENZYME STRUCTURE; FUNGUS; ION MONITORING; METHYLATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PROTEIN DOMAIN; SUBSTRATE CONCENTRATION; ENZYMOLOGY; METABOLISM;

FUNGI; LOVASTATIN; METHYLTRANSFERASES; POLYKETIDE SYNTHASES;

EID: 84952845765     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b11814     Document Type: Article

References (24)

1. Chooi, Y. H.; Tang, Y. J. Org. Chem. 2012, 77, 9933 10.1021/jo301592k
2. Cox, R. J. Org. Biomol. Chem. 2007, 5, 2010 10.1039/b704420h
3. Kennedy, J.; Auclair, K.; Kendrew, S. G.; Park, C.; Vederas, J. C.; Richard Hutchinson, C. Science 1999, 284, 1368 10.1126/science.284.5418.1368
4. 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 10.1126/science.1175602
5. Auclair, K.; Sutherland, A.; Kennedy, J.; Witter, D. J.; Van den Heever, J. P.; Hutchinson, C. R.; Vederas, J. C. J. Am. Chem. Soc. 2000, 122, 11519 10.1021/ja003216+
6. Istvan, E. S.; Deisenhofer, J. Science 2001, 292, 1160 10.1126/science.1059344
7. Khosla, C.; Herschlag, D.; Cane, D. E.; Walsh, C. T. Biochemistry 2014, 53, 2875 10.1021/bi500290t
8. Kakule, T. B.; Lin, Z.; Schmidt, E. W. J. Am. Chem. Soc. 2014, 136, 17882 10.1021/ja511087p
9. Fisch, K. M.; Bakeer, W.; Yakasai, A. A.; Song, Z.; Pedrick, J.; Wasil, Z.; Bailey, A. M.; Lazarus, C. M.; Simpson, T. J.; Cox, R. J. J. Am. Chem. Soc. 2011, 133, 16635 10.1021/ja206914q
10. Winter, J. M.; Sato, M.; Sugimoto, S.; Chiou, G.; Garg, N. K.; Tang, Y.; Watanabe, K. J. Am. Chem. Soc. 2012, 134, 17900 10.1021/ja3090498
11. Xie, X.; Meehan, M. J.; Xu, W.; Dorrestein, P. C.; Tang, Y. J. Am. Chem. Soc. 2009, 131, 8388 10.1021/ja903203g
12. Eley, K. L.; Halo, L. M.; Song, Z.; Powles, H.; Cox, R. J.; Bailey, A. M.; Lazarus, C. M.; Simpson, T. J. ChemBioChem 2007, 8, 289 10.1002/cbic.200600398
13. Ames, B. D.; Nguyen, C.; Bruegger, J.; Smith, P.; Xu, W.; Ma, S.; Wong, E.; Wong, S.; Xie, X.; Li, J. W.-H.; Vederas, J. C.; Tang, Y.; Tsai, S.-C. Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 11144 10.1073/pnas.1113029109
14. Zou, Y.; Xu, W.; Tsunematsu, Y.; Tang, M.; Watanabe, K.; Tang, Y. Org. Lett. 2014, 16, 6390 10.1021/ol503179v
15. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039 10.1021/ja00068a098
16. Ge, H.-M.; Huang, T.; Rudolf, J. D.; Lohman, J. R.; Huang, S.-X.; Guo, X.; Shen, B. Org. Lett. 2014, 16, 3958 10.1021/ol501767v
17. Oikawa, Y.; Sugano, K.; Yonemitsu, O. J. Org. Chem. 1978, 43, 2087 10.1021/jo00404a066
18. Piasecki, S. K.; Taylor, C. A.; Detelich, J. F.; Liu, J.; Zheng, J.; Komsoukaniants, A.; Siegel, D. R.; Keatinge-Clay, A. T. Chem. Biol. 2011, 18, 1331 10.1016/j.chembiol.2011.07.021
19. Keatinge-Clay, A. J. Mol. Biol. 2008, 384, 941 10.1016/j.jmb.2008.09.084
20. Wu, N.; Tsuji, S. Y.; Cane, D. E.; Khosla, C. J. Am. Chem. Soc. 2001, 123, 6465 10.1021/ja010219t
21. Yin, Y.; Lu, H.; Khosla, C.; Cane, D. E. J. Am. Chem. Soc. 2003, 125, 5671 10.1021/ja034574q
22. Winter, J. M.; Chiou, G.; Bothwell, I. R.; Xu, W.; Garg, N. K.; Luo, M.; Tang, Y. Org. Lett. 2013, 15, 3774 10.1021/ol401723h
23. Evans, S. E.; Williams, C.; Arthur, C. J.; Płoskoń, E.; Wattana-amorn, P.; Cox, R. J.; Crosby, J.; Willis, C. L.; Simpson, T. J.; Crump, M. P. J. Mol. Biol. 2009, 389, 511 10.1016/j.jmb.2009.03.072
24. Sørensen, J. L.; Hansen, F. T.; Sondergaard, T. E.; Staerk, D.; Lee, T. V.; Wimmer, R.; Klitgaard, L. G.; Purup, S.; Giese, H.; Frandsen, R. J. N. Environ. Microbiol. 2012, 14, 1159 10.1111/j.1462-2920.2011.02696.x