Facile synthesis of tetrafluorotyrosine and its application in pH triggered membrane lysis

Organic Letters

Volumn 13, Issue 2, 2011, Pages 236-239

  Wang, Fang ^a   Qin, Luoheng ^a   Wong, Patrick ^a   Gao, Jianmin ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; FLUORINATED HYDROCARBON; PEPTIDE; TETRAFLUOROTYROSINE; TYROSINE;

ARTICLE; CELL MEMBRANE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; PH; SEQUENCE HOMOLOGY; SYNTHESIS;

CELL MEMBRANE; HYDROCARBONS, FLUORINATED; HYDROGEN-ION CONCENTRATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES; SEQUENCE HOMOLOGY, AMINO ACID; TYROSINE;

EID: 78651486698     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102610q     Document Type: Article

References (26)

1. Zasloff, M. Nature 2002, 415, 389-95
2. Scott, R. W.; DeGrado, W. F.; Tew, G. N. Curr.Opin. Biotechnol. 2008, 19, 620-7
3. Porter, E. A.; Weisblum, B.; Gellman, S. H. J. Am. Chem. Soc. 2002, 124, 7324-30
4. Fernandez-Lopez, S.; Kim, H. S.; Choi, E. C.; Delgado, M.; Granja, J. R.; Khasanov, A.; Kraehenbuehl, K.; Long, G.; Weinberger, D. A.; Wilcoxen, K. M.; Ghadiri, M. R. Nature 2001, 412, 452-5
5. Chongsiriwatana, N. P.; Patch, J. A.; Czyzewski, A. M.; Dohm, M. T.; Ivankin, A.; Gidalevitz, D.; Zuckermann, R. N.; Barron, A. E. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 2794-9
6. Li, W.; Nicol, F.; Szoka, F. C., Jr. Adv. Drug. Delivery Rev. 2004, 56, 967-85
7. Turk, M. J.; Reddy, J. A.; Chmielewski, J. A.; Low, P. S. Biochim. Biophys. Acta 2002, 1559, 56-68
8. Thevenin, D.; An, M.; Engelman, D. M. Chem. Biol. 2009, 16, 754-62
9. Segala, J.; Engelman, D. M.; Reshetnyak, Y. K.; Andreev, O. A. Int. J. Mol. Sci. 2009, 10, 3478-87
10. Meng, H.; Kumar, K. J. Am. Chem. Soc. 2007, 129, 15615-22
11. Marsh, E. N.; Buer, B. C.; Ramamoorthy, A. Mol. Biosyst. 2009, 5, 1143-7
12. Hodges, J. A.; Raines, R. T. J. Am. Chem. Soc. 2005, 127, 15923-32
13. Woll, M. G.; Hadley, E. B.; Mecozzi, S.; Gellman, S. H. J. Am. Chem. Soc. 2006, 128, 15932-3
14. Zheng, H.; Comeforo, K.; Gao, J. J. Am. Chem. Soc. 2009, 131, 18-9
15. Zheng, H.; Gao, J. Angew. Chem., Int. Ed. 2010, 49, 8635-9
16. Meyer, E. A.; Castellano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1210-50
17. Waters, M. L. Curr. Opin. Chem. Biol. 2002, 6, 736-41
18. Kim, K.; Cole, P. A. J. Am. Chem. Soc. 1998, 120, 6851-8
19. Seyedsayamdost, M. R.; Yee, C. S.; Stubbe, J. Nat. Protoc. 2007, 2, 1225-35
20. Seyedsayamdost, M. R.; Reece, S. Y.; Nocera, D. G.; Stubbe, J. J. Am. Chem. Soc. 2006, 128, 1569-79
21. Filler, R.; Ayyangar, N. R.; Gustowsk., W.; Kang, H. H. J. Org. Chem. 1969, 34, 534-8
22. Rodionov, P. P.; Furin, G. G. J. Fluor. Chem. 1990, 47, 361-434
23. Feutrill, G. I.; Mirrington, R. N. Tetrahedron Lett. 1970, 1327-8
24. Dessolin, M.; Guillerez, M. G.; Thieriet, N.; Guibe, F.; Loffet, A. Tetrahedron Lett. 1995, 36, 5741-4
25. Matsuzaki, K. Biochim. Biophys. Acta 1998, 1376, 391-400
26. Lee, H. M.; Chmielewski, J. J. Pept. Res. 2005, 65, 355-63