Methylation-dependent acyl transfer between polyketide synthase and nonribosomal peptide synthetase modules in fungal natural product biosynthesis

Organic Letters

Volumn 16, Issue 24, 2014, Pages 6390-6393

  Zou, Yi ^a   Xu, Wei ^a   Tsunematsu, Yuta ^c   Tang, Mancheng ^a   Watanabe, Kenji ^c   Tang, Yi ^a,b  

^a Engineering IV   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; BIOLOGICAL FACTOR; NONRIBOSOMAL PEPTIDE SYNTHETASE; PEPTIDE SYNTHASE; POLYKETIDE SYNTHASE; PSEUROTIN; PYRONE DERIVATIVE;

AMINO ACID SEQUENCE; BIOCHEMISTRY; BIOSYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; FUNGUS; METABOLISM; METHYLATION; PROCEDURES; PROTEIN ENGINEERING;

AMINO ACID SEQUENCE; BIOCHEMICAL PROCESSES; BIOLOGICAL FACTORS; FUNGI; METHYLATION; MOLECULAR STRUCTURE; PEPTIDE SYNTHASES; POLYKETIDE SYNTHASES; PROTEIN ENGINEERING; PYRONES; PYRROLIDINONES;

EID: 84919628589     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol503179v     Document Type: Article

References (32)

1. Fisch, K. M. RSC Adv. 2013, 3, 18228
2. Boettger, D.; Hertweck, C. ChemBioChem 2013, 14, 28
3. Cox, R. J. Org. Biomol. Chem. 2007, 5, 2010
4. Chooi, Y. H.; Tang, Y. J. Org. Chem. 2012, 77, 9933
5. Bloch, P.; Tamm, C.; Bollinger, P.; Petcher, T. J.; Weber, H. P. Helv. Chim. Acta 1976, 59, 133
6. Maiya, S.; Grundmann, A.; Li, X.; Li, S. M.; Turner, G. ChemBioChem 2007, 8, 1736
7. Asami, Y.; Kakeya, H.; Onose, R.; Yoshida, A.; Matsuzaki, H.; Osada, H. Org. Lett. 2002, 4, 2845
8. Tsunematsu, Y.; Fukutomi, M.; Saruwatari, T.; Noguchi, H.; Hotta, K.; Tang, Y.; Watanabe, K. Angew. Chem., Int. Ed. 2014, 53, 8475
9. Xu, W.; Cai, X.; Jung, M. E.; Tang, Y. J. Am. Chem. Soc. 2010, 132, 13604
10. Bergmann, S.; Schumann, J.; Scherlach, K.; Lange, C.; Brakhage, A. A.; Hertweck, C. Nat. Chem. Biol. 2007, 3, 213
11. Wasil, Z.; Pahirulzaman, K. A. K.; Butts, C.; Simpson, T. J.; Lazarus, C. M.; Cox, R. J. Chem. Sci. 2013, 4, 3845
12. Gelderblom, W. C.; Jaskiewicz, K.; Marasas, W. F.; Thiel, P. G.; Horak, R. M.; Vleggaar, R.; Kriek, N. P. Appl. Environ. Microbiol. 1988, 54, 1806
13. Song, Z.; Cox, R. J.; Lazarus, C. M.; Simpson, T. T. ChemBioChem 2004, 5, 1196
14. Eley, K. L.; Halo, L. M.; Song, Z. S.; Powles, H.; Cox, R. J.; Bailey, A. M.; Lazarus, C. M.; Simpson, T. J. ChemBioChem 2007, 8, 289
15. Mcinnes, A. G.; Smith, D. G.; Wat, C. K.; Vining, L. C.; Wright, J. L. C. J. Chem. Soc., Chem. Commun. 1974, 281
16. Halo, L. M.; Heneghan, M. N.; Yakasai, A. A.; Song, Z.; Williams, K.; Bailey, A. M.; Cox, R. J.; Lazarus, C. M.; Simpson, T. J. J. Am. Chem. Soc. 2008, 130, 17988
17. Liu, X. Y.; Walsh, C. T. Biochemistry 2009, 48, 8746
18. Kakule, T. B.; Sardar, D.; Lin, Z. J.; Schmidt, E. W. ACS Chem. Biol. 2013, 8, 1549
19. Boettger, D.; Bergmann, H.; Kuehn, B.; Shelest, E.; Hertweck, C. ChemBioChem 2012, 13, 2363
20. Kakule, T. B.; Lin, Z.; Schmidt, E. W. J. Am. Chem. Soc. 2014, 10.1021/ja511087p
21. 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
22. Wiemann, P.; Guo, C. J.; Palmer, J. M.; Sekonyela, R.; Wang, C. C. C.; Keller, N. P. Proc. Natl. Acad. Sci. U.S.A. 2013, 110, 17065
23. Ma, S. M.; Li, J. W.; Choi, J. W.; Zhou, H.; Lee, K. K.; Moorthie, V. A.; Xie, X.; Kealey, J. T.; Da Silva, N. A.; Vederas, J. C.; Tang, Y. Science 2009, 326, 589
24. Lee, K. K.; Da Silva, N. A.; Kealey, J. T. Anal. Biochem. 2009, 394, 75
25. Mohr, P.; Tamm, C. Tetrahedron 1981, 37 (Supplement 1) 201
26. Crawford, J. M.; Dancy, B. C. R.; Hill, E. A.; Udwary, D. W.; Townsend, C. A. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 16728
27. Crawford, J. M.; Vagstad, A. L.; Ehrlich, K. C.; Townsend, C. A. Bioorg. Chem. 2008, 36, 16
28. Waldman, A. J.; Balskus, E. P. Org. Lett. 2014, 16, 640
29. Bao, W. L.; Sheldon, P. J.; Wendt-Pienkowsi, E.; Hutchinson, C. R. J. Bacteriol. 1999, 181, 4690
30. Zhou, H.; Gao, Z.; Qiao, K.; Wang, J.; Vederas, J. C.; Tang, Y. Nat. Chem. Biol. 2012, 8, 331
31. Oikawa, Y.; Sugano, K.; Yonemitsu, O. J. Org. Chem. 1978, 43, 2087
32. Arthur, C.; Cox, R. J.; Crosby, J.; Rahman, M. M.; Simpson, T. J.; Soulas, F.; Spogli, R.; Szafranska, A. E.; Westcott, J.; Winfield, C. J. ChemBioChem 2002, 3, 253