Dynamic cyclic thiodepsipeptide libraries from thiol-thioester exchange

Organic Letters

Volumn 12, Issue 8, 2010, Pages 1860-1863

  Gagné, Michel R ^a   Ghosh, Soumyadip ^a   Ingerman, Lindsey A ^a   Frye, Aaron G ^a   Lee, Stephen J ^b   Waters, Marcey L ^a  

^a University of North Carolina at Chapel Hill   (United States)

^b U S ARMY RESEARCH OFFICE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; DEPSIPEPTIDE; ESTER; THIOL DERIVATIVE;

ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; KINETICS;

COMBINATORIAL CHEMISTRY TECHNIQUES; DEPSIPEPTIDES; ESTERS; KINETICS; PEPTIDES, CYCLIC; SULFHYDRYL COMPOUNDS;

EID: 77951193856     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1004752     Document Type: Article

References (22)

1. Craik, D. J. Science 2006, 311, 1563-1564
2. Horswill, A. R.; Benkovic, S. J. Cell Cycle 2005, 4, 552-555
3. Horton, D. A.; Bourne, G. T.; Smythe, M. L. J. Comput. Aided Mol. Des. 2002, 16, 415-430
4. Minucci, S.; Pelicci, P. G. Nat. Rev. Cancer 2006, 6, 38-51
5. Meinke, P. T.; Liberator, P. Curr. Med. Chem. 2001, 8, 211-235
6. Shute, R. E.; Kawai, M.; Rich, D. H. Tetrahedron 1988, 44, 685-95
7. Montero, A.; Beierle, J. M.; Olsen, C. A.; Ghadiri, M. R. J. Am. Chem. Soc. 2009, 131, 3033-3041
8. Olsen, C. A.; Ghadiri, M. R. J. Med. Chem. 2009, 52, 7836-7846
9. Sidhu, S. S.; Fairbrother, W. J.; Deshayes, K. ChemBioChem 2003, 4, 14-25
10. Corbett, P. T.; Leclaire, J.; Vial, L.; West, K. R.; Wietor, J. L.; Sanders, J. K.; Otto, S. Chem. Rev. 2006, 106, 3652-3711
11. Leclaire, J.; Vial, L.; Otto, S.; Sanders, J. K. M. Chem. Commun. 2005, 1959-1961
12. Larsson, R.; Pei, Z.; Ramström, O. Angew. Chem., Int. Ed. 2004, 43, 3716-3718
13. Ura, Y.; Beierle, J. M.; Leman, L. J.; Orgel, L. E.; Ghadiri, M. R. Science 2009, 325, 73-77
14. Woll, M. G.; Gellman, S. H. J. Am. Chem. Soc. 2004, 126, 11172-11174
15. Cousins, G. R. L.; Poulsen, S.-A.; Sanders, J. K. M. Chem. Commun. 1999, 1575-1576
16. The macrocyclic thiodepsipeptides were found to hydrolyze over extended periods, but not before reaching equilibrium.
17. Hackeng, T. M.; Griffin, J. H.; Dawson, P. E. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 10068-10073
18. Brik, A.; Yang, Y. Y.; Ficht, S.; Wong, C. H. J. Am. Chem. Soc. 2006, 128, 5626-5627
19. Villain, M.; Gaertner, H.; Botti, P. Eur. J. Org. Chem. 2003, 3267, 3272
20. Rowan, S. J.; Hamilton, D. G.; Brady, P. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1997, 119, 2578-2579
21. Rowan, S. J.; Reynolds, D. J.; Sanders, J. K. M. J. Org. Chem. 1999, 64, 5804-5814
22. Nitschke, J. R. Acc. Chem. Res. 2007, 40, 103-112