97. Synthesis of Unnatural Lipophilic N-(9H-Fluoren-9-ylmethoxy)carbonyl-Substituted α-Amino Acids and Their Incorporation into Cyclic RGD-Peptides: A Structure-Activity Study

Helvetica Chimica Acta

Volumn 80, Issue 4, 1997, Pages 1280-1300

  Koppitz, Marcus ^a   Huenges, Martin ^a   Gratias, Rainer ^a   Kessler, Horst ^a   Goodman, Simon L ^b   Jonczyk, Alfred ^b  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b MERCK KGAA   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CYCLOPEPTIDE; SYNTHETIC PEPTIDE;

AMINO ACID SUBSTITUTION; ANGIOGENESIS; ARTICLE; CANCER INHIBITION; CONFORMATIONAL TRANSITION; DRUG SYNTHESIS; LIPOPHILICITY; PEPTIDE ANALYSIS; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0030797714     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.19970800423     Document Type: Article

References (85)

1. I. Toth, R. A. Hughes, G. Dekany, A. M. Hillery, P. Ward, Liebigs Ann. Chem. 1994, 685.
2. I. Toth, M. Christodoulou, K. Bankowsky, N. Flinn, W. A. Gibbons, G. Godeau, E. Moczar, W. Hornebeck, Int. J. Pharm. 1995, 125, 117.
3. H. Schild, K. Deres, K. H. Wiesmüller, G. Jung, H. G. Rammensee, Eur. J. Immunol. 1991, 21, 2649.
4. F. Al-Obeidi, V. J. Hruby, N. Yaghoubi, M. M. Marwan, J. Med. Chem. 1992, 35, 118.
5. J. Metzger, K.-H. Wiesmüller, R. Schaude, W. G. Besseler, G. Jung, Int. J. Pept. Protein Res. 1991, 37, 46.
6. H. B. A. De Bont, J. H. van Boom, R. M. J. Liskamp, Recl. Trav. Chim. Pays-Bas 1992, 111, 222.
7. C. H. Damsky, M. Bernfield, Curr. Opin. Cell Biol. 1990, 2, 813.
8. S. M. Albelda, C. A. Buck, FASEB J. 1990, 4, 2668.
9. D. Cox, T. Aoki, J. Seki, Y. Motoyama, K. Yoshida, Med. Res. Rev. 1994, 14, 195.
10. D. A. Cheresh, R. P. Mecham, 'Integrins, Molecular and Biological Responses to the Extracellular Matrix', Academic Press, London, 1994.
11. M. A. Horton, M. L. Taylor, T. R. Arnett, M. H. Helfrich, Exp. Cell Res. 1991, 195, 368.
12. D. T. Denhardt, X. Guo, FASEB J. 1993, 7, 1475.
13. M. Grano, P. Zigrino, S. Colucci, G. Zambonin, L. Trusolino, M. Serra, N. Baldini, A. Teti, P. C. Marchisio, A. Zambonin Zallone, Exp. Cell Res. 1994, 212, 209.
14. R. J. Gould, Perspectives in Drug Discovery and Design 1994, 1, 537.
15. M. Aumailly, M. Gurrath, G. Müller, J. Calvete, R. Timpl, H. Kessler, FEBS Lett. 1991, 291, 50.
16. P. C. Brooks, R. A. F. Clark, D. A. Cheresh, Science 1994, 264, 569.
17. P. C. Brooks, A. M. P. Montgomery, M. Rosenfeld, R. A. Reisfeld, T. Hu, G. Klier, D. A. Cheresh, Cell 1994, 79, 1157.
18. M. Friedlander, P. C. Brooks, R. W. Shaffer, C. M. Kincaid, J. A. Varner, D. A. Cheresh, Science 1995, 270, 1500.
19. H. P. Hammes, M. Brownlee, A. Jonczyk, A. Sutter, K. T. Preissner, Nature Medicine 1996, 2, 529.
20. H. Kessler, B. Diefenbach, D. Finsinger, A. Geyer, M. Gurrath, S. L. Goodman, G. Hölzemann, R. Haubner, A. Jonczyk, G. Müller, E. Graf von Roedern, J. Wermuth, Lett. Pept. Sci. 1995, 2, 155.
21. M. Gurrath, G. Müller, H. Kessler, M. Aumailly, R. Timpl, Eur. J. Biochem. 1992, 210, 911.
22. G. Müller, M. Gurrath, H. Kessler, R. Timpl, Angew. Chem. Int. Ed. 1992, 31, 326.
23. M. Pfaff, K. Tangemann, B. Müller, M. Gurrath, H. Kessler, R. Timpl, J. Engel. J. Biol. Chem. 1994, 269, 20233.
24. R. Haubner, R. Gratias, B. Diefenbach, S. L. Goodman, A. Jonczyk, H. Kessler, J. Am. Chem. Soc. 1996, 118, 7461.
25. N. F. Albertson, J. Am. Chem. Soc. 1946, 68, 450.
26. W. A. Gibbons, R. A. Hughes, M. Charalambous, M. Christodoulou, A. Szeto, A. E. Aulabaugh, P. Mascagni, I. Toth, Liebigs Ann. Chem. 1990, 1175.
27. H. K. Chenault, J. Dahmer, G. M. Whitesides, J. Am. Chem. Soc. 1989, 111, 6354.
28. S. M. Birnbaum, S.-C. J. Fu, J. P. Greenstein, J. Am. Chem. Soc. 1953, 203, 333.
29. F. H. C. Stewart, Austr. J. Chem. 1961, 14, 654.
30. L. A. Carpino, G. Y. Han, J. Org. Chem. 1972, 37, 3404.
31. E. Atherton, H. Fox, D. Harkiss, C. J. Logan, R. C. Sheppard, B. J. Williams, J. Chem. Soc., Chem. Commun. 1978, 537.
32. C.-D. Chang, J. Meienhofer, Int. J. Pept. Protein Res. 1978, 11, 246.
33. C.-D. Chang, Int. J. Pept. Protein Res. 1980, 15, 59.
34. M. Tessier, F. Albericio, E. Pedroso, R. Eritja, E. Giralt, C. Granier, J. Van Rietschoten, Int. J. Pept. Protein Res. 1983, 22, 125.
35. G. Barcelo, J.-P. Senet, G. Senney, J. Bensoam, A. Loffet, Synthesis 1986, 627.
36. P. Henklein, H.-V. Heyne, W. R. Halatsch, H. Niedlich, Synthesis 1987, 166.
37. L. Lapatsanis, G. Milias, K. Frouissios, M. Kolovos, Synthesis 1983, 671.
38. P. B. W. Ten Kortenaar, B. G. Van Diyk, M. Peeters, B. J. Raaben, P. J. H. Adam, G. I. Tesser, Int. J. Pept. Protein Res. 1986, 27, 398.
39. H. R. Kricheldorf, Liebigs Ann. Chem. 1972, 763, 17.
40. H. R. Kricheldorf, M. Fehrle, Chem. Ber. 1974, 107, 3533.
41. K. Barlos, D. Papaioannou, D. Theodoropoulos, J. Org. Chem. 1982, 47, 1324.
42. D. R. Bolin, I. L. Sytwu, F. Humiec, J. Meienhofer, Int. J. Pept. Protein Res. 1989, 33, 353.
43. L. A. Carpino, J. Am. Chem. Soc. 1970, 92, 5748.
44. G. B. Fields, R. L. Noble, Int. J. Pept. Protein Res. 1990, 35, 161.
45. R. B. Merrifield, J. Am. Chem. Soc. 1963, 85, 2149.
46. R. B. Merrifield, Angew. Chem. 1985, 97, 801.
47. K. Barlos, O. Chatzi, D. Gatos, G. Stavropoulos, Int. J. Pept. Prot. Res. 1991, 37, 513.
48. S. F. Brady, S. L. Varada, R. M. Freidinger, D. A. Schwenk, M. Mendlowski, F. W. Holly, D. F. Veber, J. Org. Chem. 1979, 44, 3101.
49. J. D. Dunitz, J. Waser, J. Am. Chem. Soc. 1972, 94, 5645.
50. H. Kessler, P. Krämer, G. Krack, Isr. J. Chem. 1980, 20, 180.
51. H. Kessler, 'Conformational Mobility of the Backbone of Cyclic Tripeptides', in 'Stereodynamics of Molecular Systems', Ed. R. H. Sarma, Pergamon Press, Oxford-New York-Frankfurt-Paris, 1979, pp. 187.
52. H. Kessler, R. Gratias, G. Hessler, M. Gurrath, G. Müller, Pure Appl. Chem. 1996, 68, 1201.
53. H. Kessler, S. Seip, 'NMR of Peptides' in 'Two-Dimensional NMR Spectroscopy: Applications of Chemists and Biochemists', Eds. W. R. Croasmun and R. M. K. Carlson, VCH Publishers, New York, 1994, pp. 619.
54. M. Eberstadt, G. Gemmecker, D. F. Mierke, H. Kessler, Angew. Chem. Int. Ed. 1995, 34, 1671.
55. D. F. Mierke, M. Kurz, H. Kessler, J. Am. Chem. Soc. 1993, 116, 1042.
56. H. Kessler, J. W. Bats, L. Lautz, A. Müller, Liebigs Ann. Chem. 1989, 913.
57. K. Romanowska, K. D. Kopple, Int. J. Pept. Protein Res. 1987, 30, 289.
58. W. Koenig, R. Geiger, Chem. Ber. 1970, 103, 788.
59. L. Braunschweiler, R. R. Ernst, J. Magn. Reson. 1983, 53, 521.
60. A. Bax, R. A. Byrd, A. Aszalos, J. Am. Chem. Soc. 1984, 106, 7632.
61. A. Bax, D. G. Davis, J. Magn. Reson. 1985, 65, 355.
62. L. Müller, J. Magn. Reson. 1987, 72, 191.
63. A. Bax, L. Lerner, J. Magn. Reson. 1988, 79, 429.
64. D. Marion, A. Bax, J. Magn. Reson. 1988, 80, 528.
65. A. A. Bothner-By, R L. Stephens, J. Lee, D. C. Warren, R. W. Jeanloz, J. Am. Chem. Soc. 1984, 106, 811.
66. A. Bax, D. G. Davis, J. Magn. Reson. 1985, 63, 207.
67. D. Neuhaus, J. Keeler, J. Magn. Reson. 1986, 68, 568.
68. C. Griesinger, R. R. Ernst, J. Magn. Reson. 1987, 75, 261.
69. H. Kessler, C. Griesinger, R. Kerssebaum, K. Wagner, R. R. Ernst, J. Am. Chem. Soc. 1987, 109, 607.
70. M. R. Bendall, D. T. Pegg, D. M. Dodrell, J. Magn. Reson. 1983, 52, 81.
71. A. Bax, R. H. Griffey, B. L. Hawkins, J. Am. Chem. Soc. 1983, 105, 7188.
72. A. Bax, R. H. Griffey, B. L. Hawkins, J. Magn. Reson. 1983, 55, 301.
73. L. Lerner, A. Bax, J. Magn. Reson. 1986, 69, 375.
74. A. Bax, M. T. Summers, J. Am. Chem. Soc. 1986, 108, 2093.
75. D. Neuhaus, M. Williamson, 'The Nuclear Overhauser Effect in Structural and Conformational Analysis', VCH Publishers, New York, 1989.
76. Y. Kim, J. H. Prestegard, J. Magn. Reson. 1989, 84, 9.
77. D. F. Mierke, H. Kessler, Biopolymers 1993, 33, 1003.
78. T. F. Havel, Prog. Biophys. Molec. Biol. 1991, 56, 43.
79. G. M. Crippen, T. F. Havel, 'Distance Geometry and Molecular Conformation', Research Studies Press LTD., Somerset, England, John Wiley & Sons, New York, 1988.
80. T. F. Havel, 'DISGEO, Quantum Chemistry Exchange Program', Exchange No. 507, Indiana University, 1986.
81. T. F. Havel, K. Wüthrich, Bull. Math. Bio. 1984, 46, 673.
82. R. Haubner, W. Schmitt, G. Hölzemann, S. L. Goodman, A. Jonczyk, H. Kessler, J. Am. Chem. Soc. 1996, 118, 7881.
83. M. Karplus, J. Chem. Phys. 1959, 30, 11.
84. M. Karplus, J. Am. Chem. Soc. 1963, 85, 2870.
85. V. F. Bystrov, Prog. Nucl. Magn. Reson. Spectrosc. 1976, 10, 41.