Synthesis of trifluoromethyl-substituted proline analogues as19F NMR labels for peptides in the polyproline II conformation

Angewandte Chemie - International Edition

Volumn 47, Issue 31, 2008, Pages 5765-5767

  Mykhailiuk, Pavel K ^a,b,c   Afonin, Sergii ^a   Palamarchuk, Gennady V ^d   Shishkin, Oleg V ^d   Ulrich, Anne S ^a   Komarov, Igor V ^b,c  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^b TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

^c ENAMINE LTD   (Ukraine)

^d INSTITUTE FOR SINGLE CRYSTALS   (Ukraine)

Author keywords

Amino acids; Conformation analysis; Fluorine; NMR spectroscopy; Peptides

Indexed keywords

AMINO ACIDS; CONFORMATION ANALYSIS; FLUORINE; NMR SPECTROSCOPY; PEPTIDES;

SYNTHESIS (CHEMICAL);

DRUG DERIVATIVE; FLUORINE; PEPTIDE; PROLINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; PROTEIN CONFORMATION; SYNTHESIS;

CIRCULAR DICHROISM; FLUORINE; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PEPTIDES; PROLINE; PROTEIN CONFORMATION;

EID: 53549126092     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801022     Document Type: Article

References (37)

1. a) M. W. MacArthur, J. M. Thornton, J. Mol. Biol. 1991, 218, 397-412;
2. b) L. J. Ball, R. Kühne, J. Schneider-Mergener, H. Oschkinat, Angew. Chem. 2005, 117, 2912-2930;
3. Angew. Chem. Int. Ed. 2005, 44, 2852-2869.
4. a) A. A. Adzhubei, M. J. Sternberg, J. Mol. Biol. 1993, 229, 472-493;
5. b) P. M. Cowan, S. McGavin, A. C. North, Nature 1955, 176, 1062-1064;
6. c) R. Zhang, J. S. Madalengoitia, Tetrahedron Lett. 1996, 37, 6235-6238.
7. a) M. P. Williamson, Biochem. J. 1994, 297, 249-260;
8. b) F. Rabanal, M. D. Ludevid, M. Pons, E. Giralt, Biopolymers 1993, 33, 1019-1028;
9. c) B. Bochicchio, A. M. Tamburro, Chirality 2002, 14, 782-792.
10. a) N. Sreerama, R. W. Woody, Biochemistry 1994, 33, 10022-10025;
11. b) P. Y. Chou, G. D. Fasman, Annu. Rev. Biochem. 1978, 47, 251-276;
12. c) G. M. Rubin, et al., Science 2000, 287, 2204-2215. See the Supporting Information for the full citation.
13. a) P. Tompa, FEBS Lett. 2005, 579, 3346-3354;
14. b) A. Rath, A. R. Davidson, C. M. Deber, Biopolymers 2005, 80, 179-185;
15. c) A. L. Rucker, T. P. Creamer, Protein Sci. 2002, 11, 980-985;
16. d) R. K. Dukor, T. A. Keiderling, Biopolymers 1991, 31, 1747-1761.
17. a) A. S. Ulrich, Prog. Nucl. Magn. Reson. Spectrosc. 2005, 46, 1-21;
18. b) J. J. Buffy, A. J. Waring, M. Hong, J. Am. Chem. Soc. 2005, 127, 4477-4483.
19. 19F-nuclear magnetic resonance analysis of membrane-active peptides": A. S. Ulrich, P. Wadhwani, U. H. N. Dürr, S. Afonin, R. W. Glaser, E. Strandberg, P. Tremouilhac, C. Sachse, M. Berditchevskaia, S. Grage in NMR spectroscopy of biological solids (Ed.: A. Ramamoorthy), CRC, Boca Raton, FL, 2006, pp. 215-236.
20. a) S. Afonin, R. W. Glaser, M. Berditchevskaia, P. Wadhwani, K.-H. Gührs, U. Möllmann, A. Perner, A. S. Ulrich, ChemBioChem 2003, 4, 1151-1163;
21. b) S. Afonin, U. H. N. Dürr, R. W. Glaser, A. S. Ulrich, Magn. Reson. Chem. 2004, 42, 195-203;
22. c) P. K. Mikhailiuk, S. Afonin, A. N. Chernega, E. B. Rusanov, M. O. Platonov, G. G. Dubinina, M. Berditsch, A. S. Ulrich, I. V. Komarov, Angew. Chem. 2006, 118, 5787-5789;
23. Angew. Chem. Int. Ed. 2006, 45, 5659-5661;
24. d) S. Afonin, P. K. Mikhailiuk, I. V. Komarov, A. S. Ulrich, J. Pept. Sci. 2007, 13, 614-623.
25. a) X. Qiu, F. Qing, J. Chem. Soc. Perkin Trans. 1 2002, 2052-2057;
26. b) X. L. Qiu, F. L. Qing, J. Org. Chem. 2002, 67, 7162-7164;
27. c) J. R. Del Valle, M. Goodman, Angew. Chem. 2002, 114, 1670-1672;
28. Angew. Chem. Int. Ed. 2002, 41, 1600-1602.
29. G . Chaume, M. C. Van Severen, S. Marinkovic, T. Brigaud, Org. Lett. 2006, 8, 6123-6126.
30. a) K. Burger, K. Mütze, W. Hollweck, B. Koksch, Tetrahedron 1998, 54, 5915-5928;
31. b) C. Schierlinger, K. Burger, Tetrahedron Lett. 1992, 33, 193-194.
32. a) P. Le Maux, S. Juillard, G. Simmoneaux, Synthesis 2006, 1701-1704;
33. b) P. K. Mykhailiuk, S. Afonin, A. S. Ulrich, I. V. Komarov, Synthesis 2008, 1757-1760.
34. K. K. Schumacher, J. Jiang, M. M. Joullie, Tetrahedron: Asymmetry 1998, 9, 47-53.
35. One of the isomers of 13 was isolated and studied by X-ray crystallograpy (see the Supporting Information).
36. J . Fernández-Carneado, M. J. Kogan, S. Castel, E. Giralt, Angew. Chem. 2004, 116, 1847-1850;
37. Angew. Chem. Int. Ed. 2004, 43, 1811-1814.