Synthesis and Incorporation of α-Trifluoromethyl-Substituted Amino Acids into Peptides

ACS Symposium Series

Volumn 639, Issue , 1996, Pages 42-58

  Koksch, Beate ^a   Sewald, Norbert ^a   Jakubke, Hans Dieter ^a   Burger, Klaus ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1842473844     PISSN: 00976156     EISSN: None     Source Type: Book Series    
DOI: None     Document Type: Article

References (64)

1. Giannis, A.; Kolter, T. Angew. Chem. 1993, 105, 1303; Angew. Chem., Int. Ed. Engl. 1993, 32, 1244, and references cited therein.
2. Giannis, A.; Kolter, T. Angew. Chem. 1993, 105, 1303; Angew. Chem., Int. Ed. Engl. 1993, 32, 1244, and references cited therein.
3. Toniolo, C; Benedetti, E. Macromolecules 1991, 24, 4004.
4. Marshal, G.R.; Clare, J.D.; Dunbar, J.B., jr.; Smith, G.D.; Zabrocki, J.; Redlinski, A.S.; Leplawy, M.T. Int J. Pept. Protein Res. 1988, 32, 544.
5. Burger, K.; Mütze, K.; Hollweck, W.; Koksch, B.; Kuhl, P.; Jakubke, H.-D.; Riede, J.; Schier, A. J. prakt. Chem. 1993, 335, 321.
6. Fujita, T. Prog. Phys. Org. Chem. 1983, 14, 75.
7. Muller, N. J. Pharm. Sci. 1986, 75, 987.
8. Nagai, T.; Nishioka, G.; Koyama, M.; Ando, A.; Miki, T.; Kumadaki, I. J. Fluorine Chem. 1992, 57, 320.
9. Koksch, B.; Gußmann, M.; Sewald, N.; Heckel, M.; Hiller, W.; Pink, M.; Burger, K.; Jakubke, H.-D.; Hofmann, H.-J., manuscript in preparation.
10. Welch, J.T., in: Selective Fluorination in Organic and Bioorganic Chemistry, Welch, J.T. (Ed.), ACS Symposium Series, No. 456, ACS Washington DC, 1991, 1, and references cited therein.
11. Sewald, N.; Burger, K. in: Synthesis of β-Fluorine-containing Amino Acids, Synthesis and Properties, Kukhar' V.P., Soloshonok, V.A. (Eds.), Wiley & Sons, 1995, 139, and references cited therein.
12. Sewald, N.; Hollweck, W.; Mütze, K.; Schierlinger, C.; Seymour, L.C.; Gaa, K.; Burger, K.; Koksch, B.; Jakubke, H.-D. Amino Acids, 1995, 8, 187, and references cited therein.
13. Galushko, S.V.; Shiskina, I.P.; Kobzev, S.P.; Soloshonok, V.A.; Yagupol'skii, Yu.L.; Kukhar', V.P. Zh. Anal. Khim. 1988, 43, 2067; C.A. 1989, 110, 111035z.
14. Galushko, S.V.; Shiskina, I.P.; Kobzev, S.P.; Soloshonok, V.A.; Yagupol'skii, Yu.L.; Kukhar', V.P. Zh. Anal. Khim. 1988, 43, 2067; C.A. 1989, 110, 111035z.
15. Keller, J.W.; Dick, K.O.J. Chromatogr. 1986, 367, 187.
16. Keller, J.W.; Hamilton, B.J. Tetrahedron Lett. 1986, 1249.
17. Sewald, N.; Seymour, L.C.; Burger, K.; Osipov, S.N.; Kolomiets, A.F.; Fokin, A.V. Tetrahedron: Asymmetry 1994, 5, 1051.
18. Burger, K.; Gaa, K. Chem.-Ztg. 1990, 114, 101.
19. Kobzev, S.P.; Soloshonok, V.A.; Galushko, S.V.; Yagupor'skii, Yu.L.; Kukhar', V.P. Zh. Obshch. Khim. 1989, 59, 909; J. Gen. Chem. USSR, 1989, 59, 801.
20. Kobzev, S.P.; Soloshonok, V.A.; Galushko, S.V.; Yagupor'skii, Yu.L.; Kukhar', V.P. Zh. Obshch. Khim. 1989, 59, 909; J. Gen. Chem. USSR, 1989, 59, 801.
21. a) Burger, K.; Höss, E.; Gaa, K.; Sewald, N.; Schierlinger, C.Z. Naturforsch. 1991, 46b, 361.
22. b) Schierlinger, C. PhD Thesis, Technical University Munich, 1991.
23. Mütze, K. PhD Thesis, Technical University Munich, 1993.
24. Hollweck, W. PhD Thesis, Technical University Munich, 1994.
25. Hollweck, W.; Burger, K. J. prakt. Chem. 1995, 337, 391.
26. Schierlinger, C.; Burger, K. Tetrahedron Lett. 1992, 193.
27. Burger, K.; Hollweck, W. Synlett 1994, 751.
28. Weygand, F.; Steglich, W.; Oettmeier, W.; Maierhofer, A.; Loy, R.S. Angew. Chem. 1966, 78, 640; Angew. Chem., Int. Ed. Engl. 1966, 5, 600.
29. Weygand, F.; Steglich, W.; Oettmeier, W.; Maierhofer, A.; Loy, R.S. Angew. Chem. 1966, 78, 640; Angew. Chem., Int. Ed. Engl. 1966, 5, 600.
30. a) Bambino, F.; Brownlee, R.T.C.; Chiu, F.C.K. Tetrahedron Lett. 1991, 32, 3407.
31. b) Altmann, K.-H.; Altmann, E.; Mutter, M. Helv. Chim. Acta 1992, 75, 1198.
32. Burger, K.; Schierlinger, C.; Hollweck, W.; Mütze, K. Liebigs Ann. Chem. 1994, 399.
33. Sewald, N.; Hollweck, W.; Mütze, K.; Seymour, L.C. Osipov, S.N.; Schierlinger, C.; Burger, K.; Koksch, B.; Jakubke, H.-D. in: Peptides: Proceedings of the Twenty-Third European Peptide Symposium, Maia, H.L.S. (Ed.), Escom 1995, 327.
34. Ugi, I.; Angew. Chem. 1982, 94, 826; Angew. Chem., Int. Ed. Engl. 1982, 21, 810.
35. Ugi, I.; Angew. Chem. 1982, 94, 826; Angew. Chem., Int. Ed. Engl. 1982, 21, 810.
36. Osipov, S.N.; Sewald, N.; Kolomiets, A.F.; Fokin; A.V., Burger, K. Tetrahedron Lett. 1996, 615.
37. Gante, J. Synthesis 1989, 405, and references cited therein.
38. Burger, K.; Schierlinger, C.; Mütze, K.; HoUweck, W. Liebigs Ann. Chem. 1994, 407.
39. Koksch, B. PhD Thesis, University Leipzig, 1995.
40. Gerisch, S. PhD Thesis, University Leipzig, in preparation.
41. Jakubke, H.-D., J. Chin. Chem. Soc. 1994, 41, 355.
42. Schechter, I.; Berger, A., Biochem. Biophys. Res. Commun. 1968, 32, 888.
43. Schellenberger, V.; Schellenberger, U.; Mitin, Y. V.; Jakubke, H.-D. FEBS Lett. 1990, 187, 163.
44. Koksch, B.; Sewald, N., manuscript in preparation.
45. Duttler, H.; Bizzozero, S., Acc. Chem. Res. 1989, 22, 322.
46. Tulinsky, A.; Blevins, R.A. J. Biol. Chem. 1987, 262, 7737; BH, PDB file: 6cha.pdb
47. Ladram, A.; Bulant, M.; Delfour, A.; Montagne, J. J.; Vaudry, H.; Nicolas, P. Biochimie 1994, 76, 320.
48. Metcalf, G.; Jackson, I. M. D. Ann. NY Acad. Sci., 1989, 553, 1.
49. Bauer, K.; Nowak, P.; Kleinkauf, H. Eur. J. Biochem., 1981, 118, 173.
50. Koksch, B.; Ullmann, D.; Jakubke, H.-D.; Burger, K.J. Fluorine Chem., submitted.
51. Bauer, K.; Carmelit, P.; Schulz, M.; Baes, M.; Denef, C. Endocrinology, 1990, 127, 1224.
52. Koksch, B.; Ullmann, D.; Jakubke, H.-D.; Sewald, N.; Burger, K in: Peptides: Proceedings of the Twenty-Third European Peptide Symposium Maia, H.L.S. (Ed.) Escom 1995, 323.
53. Grant, G.; Ling, N.; Rivier, J.; Vale, W. Biochemistry 1972, 11, 3070.
54. Conn, P. M.; Crowley, W. F. New Engl. J. Med. 1991, 324, 93.
55. Vickery, B. H.; Nestor I. I. Jr.; Hafez, E. S. E. in: "LHRH and its Analogs" Contraceptive and Therapeutic Applications, MTP Press Limited, 1984.
56. Gupta, H. M.; Talwar, G. P.; Salunke, D. M. Proteins: Structure, Function, and Genetics 1993, 16, 48.
57. Koksch, B.; Ullmann, D.; Sewald, N.; Burger, K.; H.-D. Jakubke, manuscript in preparation.
58. Munekata, E. Comp. Biochem. Physiol. 1991, 98C, 1, 171.
59. Nicoll, R. A., Ann. Rev. Neurosci. 1980, 3, 227.
60. Maggi, C. A.; Patacchini, R.; Rovero, P.; Giachetti, A. J. Auton. Pharmacol. 1993, 13, 23.
61. Bergmann, J.; Bienert, M.; Niedrich, H.; Mehlis, B.; Oehme, P. Experientia 1974, 30, 401.
62. Jenmalm, A.; Luthman, K.; Lindeberg, G.; Nyberg, F.; Terenius, L.; Hacksell, U. Bioorg. Med. Chem. Lett. 1992, 2, 12, 1693.
63. Couture, R.; Founder, A.; Magnan, J.; St-Pierre, S.; Regoli, D. Can. J. Physiol. Pharmacol. 1979, 57, 1427.
64. Koksch, B.; Sewald, N.; Burger, K.; H.-D. Jakubke, manuscript in preparation.