Incorporation of CF3-pseudoprolines into peptides: A methodological study

Journal of Organic Chemistry

Volumn 78, Issue 20, 2013, Pages 10144-10153

  Chaume, Grégory ^a   Simon, Julien ^a   Caupène, Caroline ^a   Lensen, Nathalie ^a   Miclet, Emeric ^b   Brigaud, Thierry ^a  

^a Université Paris Seine   (France)

^b Centre National de la Recherche Scientifique   (France)

Author keywords

[No Author keywords available]

Indexed keywords

C-TERMINAL POSITIONS; DIASTEREOMERIC; METHODOLOGICAL STUDIES; NUCLEOPHILICITIES; PEPTIDE BACKBONES; PEPTIDE COUPLING; STANDARD PROTOCOLS; TRIFLUOROMETHYL;

AMINO ACIDS; CHAINS; CHEMICAL REACTIONS; CHLORINE COMPOUNDS;

PEPTIDES;

AMIDE; AMINO ACID; DIPEPTIDE; FLUORINE DERIVATIVE; NUCLEOPHILE; OXAZOLIDINE DERIVATIVE; PEPTIDE DERIVATIVE; PROLINE DERIVATIVE; TRIPEPTIDE; DRUG DERIVATIVE; FLUOROCARBON; PEPTIDE; PROLINE; PSEUDOPROLINE; THIAZOLE DERIVATIVE;

AMIDIFICATION; AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CHEMICAL REACTION; CIS TRANS ISOMERISM; CROSS COUPLING REACTION; DIASTEREOISOMER; PROTEIN CONFORMATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS; CHEMISTRY; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

AMIDES; AMINO ACIDS; FLUOROCARBONS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PEPTIDES; PROLINE; THIAZOLES;

EID: 84886423039     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401494q     Document Type: Article

References (74)

1. Momany, F. A.; McGuire, R. F.; Burgess, A. W.; Scheraga, H. A. J. Phys. Chem. 1975, 79, 2361-2381
2. Zimmerman, S. S.; Scheraga, H. A. Macromolecules 1976, 9, 408-416
3. Stewart, D. E.; Sarkar, A.; Wampler, J. E. J. Mol. Biol. 1990, 214, 253-260
4. Fischer, S.; Dunbrack, R. L.; Karplus, M. J. Am. Chem. Soc. 1994, 116, 11931-11937
5. Kern, D.; Schutkowski, M.; Drakenberg, T. J. Am. Chem. Soc. 1997, 119, 8403-8408
6. Levitt, M. J. Mol. Biol. 1981, 145, 251-263
7. Salahuddin, A. J. Biosci. 1984, 6, 349-355
8. Wedemeyer, W. J.; Welker, E.; Scheraga, H. A. Biochemistry 2002, 41, 14637-14644
9. Chen, J.; Edwards, S. A.; Gräter, F.; Baldauf, C. J. Phys. Chem. B 2012, 116, 9346-9351
10. Karoyan, P.; Sagan, S.; Lequin, O.; Quancard, J.; Lavielle, S.; Chassaing, G. Substituted prolines: Syntheses and applications in structure-activity relationship studies of biologically actives peptides. In Targets in Heterocyclic Systems-Chemistry and Properties; Attanasi, O. A.; Spinelli, D., Eds.; Royal Society of Chemistry: Cambridge, 2005; pp 216-273.
11. Dugave, C., Ed.; Cis-Trans Isomerization in Biochemistry; Weinheim: Wiley-VCH, 2006.
12. Dugave, C.; Demange, L. Chem. Rev. 2003, 103, 2475-2532
13. Che, Y.; Marshall, G. R. Biopolymers 2006, 81, 392-406
14. Tuchscherer, G.; Mutter, M. Chimia 2001, 55, 306-313
15. Wöhr, T.; Mutter, M. Tetrahedron Lett. 1995, 36, 3847-3848
16. Guichou, J.-F.; Patiny, L.; Mutter, M. Tetrahedron Lett. 2002, 43, 4389-4390
17. Dumy, P.; Keller, M.; Ryan, D. E.; Rohwedder, B.; Wöhr, T.; Mutter, M. J. Am. Chem. Soc. 1997, 119, 918-925
18. Keller, M.; Sager, C.; Dumy, P.; Schutkowski, M.; Fischer, G. S.; Mutter, M. J. Am. Chem. Soc. 1998, 120, 2714-2720
19. Mutter, M.; Wöhr, T.; Gioria, S.; Keller, M. Biopolym.: Pept. Sci. 1999, 51, 121-128
20. Jamet, H.; Jourdan, M.; Dumy, P. J. Phys. Chem. B 2008, 112, 9975-9981
21. Kern, D.; Schutkowski, M.; Drakenberg, T. J. Am. Chem. Soc. 1997, 119, 8403-8408
22. Kang, Y. K.; Park, H. S. J. Phys. Chem. B 2007, 111, 12551-12562
23. Sager, C.; Mutter, M.; Dumy, P. Tetrahedron Lett. 1999, 40, 7987-7991
24. Ruckle, T.; de Lavallaz, P.; Keller, M.; Dumy, P.; Mutter, M. Tetrahedron 1999, 55, 11281-11288
25. Skropeta, D.; Jolliffe, K. A.; Turner, P. J. Org. Chem. 2004, 69, 8804-8809
26. Sayyadi, N.; Skropeta, D.; Jolliffe, K. A. Org. Lett. 2005, 7, 5497-5499
27. Fairweather, K. A.; Sayyadi, N.; Luck, I. J.; Clegg, J. K.; Jolliffe, K. A. Org. Lett. 2010, 12, 3136-3139
28. Haack, T.; Mutter, M. Tetrahedron Lett. 1992, 33, 1589-1592
29. Wöhr, T.; Wahl, F.; Nefzi, A.; Rohwedder, B.; Sato, T.; Sun, X.; Mutter, M. J. Am. Chem. Soc. 1996, 118, 9218-9227
30. Sampson, W. R.; Patsiouras, H.; Ede, N. J. J. Pept. Sci. 1999, 5, 403-409
31. Keller, M.; Miller, A. D. Bioorg. Med. Chem. Lett. 2001, 11, 857-859
32. Abedini, A.; Raleigh, D. P. Org. Lett. 2005, 7, 693-696
33. Ullmann, V.; Rädisch, M.; Boos, I.; Freund, J.; Pöhner, C.; Schwarzinger, S.; Unverzagt, C. Angew. Chem., Int. Ed. 2012, 51, 11566-11570
34. El Oualid, F.; Merkx, R.; Ekkebus, R.; Hameed, D. S.; Smit, J. J.; de Jong, A.; Hilkmann, H.; Sixma, T. K.; Ovaa, H. Angew. Chem., Int. Ed. 2010, 49, 10149-10153
35. Wittelsberger, A.; Keller, M.; Scarpellino, L.; Patiny, L.; Acha-Orbea, H.; Mutter, M. Angew. Chem., Int. Ed. 2000, 39, 1111-1115
36. Keller, M.; Wöhr, T.; Dumy, P.; Patiny, L.; Mutter, M. Chem.-Eur. J. 2000, 6, 4358-4363
37. Keller, M.; Boissard, C.; Patiny, L.; Chung, N. N.; Lemieux, C.; Mutter, M.; Schiller, P. W. J. Med. Chem. 2001, 44, 3896-3903
38. Tuchscherer, G.; Grell, D.; Tatsu, Y.; Durieux, P.; Fernandez-Carneado, J.; Hengst, B.; Kardinal, C.; Feller, S. Angew. Chem., Int. Ed. 2001, 40, 2844-2848
39. Keller, M.; Wöhr, T.; Dumy, P.; Patiny, L.; Mutter, M. Chem.-Eur. J. 2002, 8, 2516-2525
40. Patiny, L.; Guichou, J.-F.; Keller, M.; Turpin, O.; Ruckle, T.; Lhote, P.; Buetler, T. M.; Ruegg, U. T.; Wenger, R. M.; Mutter, M. Tetrahedron 2003, 59, 5241-5249
41. Wittelsberger, A.; Patiny, L.; Slaninova, J.; Barberis, C.; Mutter, M. J. Med. Chem. 2005, 48, 6553-6562
42. Chierici, S.; Jourdan, M.; Figuet, M.; Dumy, P. Org. Biomol. Chem. 2004, 2, 2437-2441
43. Zhang, B.; Gong, J.; Yanga, Y.; Dong, S. J. Pept. Sci. 2011, 17, 601-603
44. Davis, M. R.; Singh, E. K.; Wahyudi, H.; Alexander, L. D.; Kunicki, J. B.; Nazarova, L. A.; Fairweather, K. A.; Giltrap, A. M.; Joliffe, K. A.; McAlpine, S. R. Tetrahedron 2012, 68, 1029-1051
45. Yoder, N. C.; Kumar, K. Chem. Soc. Rev. 2002, 31, 335-341
46. Böhm, H.-J.; Banner, D.; Bendels, S.; Kansy, M.; Kunh, B.; Müller, K.; Obst-Sander, U.; Stahl, M. ChemBioChem 2004, 5, 637-643
47. Jaeckel, C.; Koksch, B. Eur. J. Org. Chem. 2005, 4483-4503
48. Meng, H.; Kumar, K. J. Am. Chem. Soc. 2007, 129, 15615-15622
49. Salwiczek, M.; Nyakatura, E. K.; Gerling, U. I. M.; Ye, S.; Koksch, B. Chem. Soc. Rev. 2012, 41, 2135-2171
50. Purser, S.; Moore, P. R.; Swallowb, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330
51. Ojima, I., Ed.; Fluorine in Medicinal Chemistry and Chemical Biology; John Wiley & Sons Ltd.: Chichester, U.K., 2009.
52. Mikhailiuk, P. K.; Afonin, S.; Chernega, A. N.; Rusanov, E. B.; Platonov, M. O.; Dubinina, G. G.; Berditsch, M.; Ulrich, A. S.; Komarov, I. V. Angew. Chem., Int. Ed. 2006, 45, 5659-5661
53. Jackson, J. C.; Hammill, J. T.; Mehl, R. A. J. Am. Chem. Soc. 2007, 129, 1160-1166
54. Mykhailiuk, P. K.; Afonin, S.; Palamarchuk, G. V.; Shishkin, O. V.; Ulrich, A. S.; Komarov, I. V. Angew. Chem., Int. Ed. 2008, 47, 5765-5767
55. Maisch, D.; Wadhwani, P.; Afonin, S.; Bottcher, C.; Koksch, B.; Ulrich, A. S. J. Am. Chem. Soc. 2009, 131, 15596-15597
56. Wadhwani, P.; Strandberg, E.; Heidenreich, N.; Bürck, J.; Fanghänel, S.; Ulrich, A. S. J. Am. Chem. Soc. 2012, 134, 6512-6515
57. Qiu, X.-L.; Qing, F.-L. Eur. J. Org. Chem. 2011, 3261-3278
58. Aceña, J. L.; Sorochinsky, A. E.; Soloshonok, V. A. Synthesis 2012, 44, 1591-1602
59. Huguenot, F.; Brigaud, T. J. Org. Chem. 2006, 71, 7075-7078
60. Chaume, G.; Van Severen, M.-C.; Marinkovic, S.; Brigaud, T. Org. Lett. 2006, 8, 6123-6126
61. Chaume, G.; Van Severen, M.-C.; Ricard, L.; Brigaud, T. J. Fluorine Chem. 2008, 129, 1104-1109
62. Caupène, C.; Chaume, G.; Ricard, L.; Brigaud, T. Org. Lett. 2009, 11, 209-212
63. Simon, J.; Nguyen, T. T.; Chelain, E.; Lensen, N.; Pytkowicz, J.; Chaume, G.; Brigaud, T. Tetrahedron: Asymmetry 2011, 22, 309-314
64. Chaume, G.; Lensen, N.; Caupène, C.; Brigaud, T. Eur. J. Org. Chem. 2009, 5717-5724
65. Chaume, G.; Barbeau, O.; Lesot, P.; Brigaud, T. J. Org. Chem. 2010, 75, 4135-4145
66. Feytens, D.; Chaume, G.; Chassaing, G.; Lavielle, S.; Brigaud, T.; Byun, B. J.; Kang, Y. K.; Miclet, E. J. Phys. Chem. B 2012, 116, 4069-4079
67. Chaume, G.; Feytens, D.; Chassaing, G.; Lavielle, S.; Brigaud, T.; Miclet, E. New J. Chem. 2013, 37, 1336-1342
68. Dal Pozzo, A.; Bergonzi, R.; Ni, M. Tetrahedron Lett. 2001, 42, 3925-3927
69. Dal Pozzo, A.; Ni, M.; Muzi, L.; Caporale, A.; de Castiglione, R.; Kaptein, B.; Broxterman, Q. B.; Formaggio, F. J. Org. Chem. 2002, 67, 6372-6375
70. Patil, K. B. S.; Babu, V. V. S. Lett. Pept. Sci. 2002, 9, 227-229
71. Ando, W.; Igarashi, Y.; Huang, L. Chem. Lett. 1987, 16, 1361-1364
72. Jeong, Y.-C.; Anwar, M.; Nguyen, T. M.; Tan, B. S. W.; Chai, C. L. L.; Moloney, M. G. Org. Biomol. Chem. 2011, 9, 6663-6669
73. Clegg, J. K.; Cochrane, J. R.; Sayyadi, N.; Skropeta, D.; Turner, P.; Joliffe, K. A. Aust. J. Chem. 2009, 62, 711-719
74. Pascal, R.; Sola, R. Tetrahedron Lett. 1998, 39, 5031-5034