New open-chain and cyclic tetrapeptides, consisting of α-, β2-, and β3-amino-acid residues, as somatostatin mimics - A survey

Helvetica Chimica Acta

Volumn 91, Issue 9, 2008, Pages 1736-1786

  Seebach, Dieter ^a   Dubost, Estelle ^a   Mathad, Raveendra I ^a   Jaun, Bernhard ^a   Limbach, Michael ^a   Löweneck, Markus ^a   Flögel, Oliver ^a   Gardiner, James ^a   Capone, Stefania ^a   Beck, Albert K ^a   Widmer, Hans ^b   Langenegger, Daniel ^b   Monna, Dominique ^b   Hoyer, Daniel ^b  

^a HCI Hönggerberg   (Switzerland)

^b NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ACID RESIDUES; BRAIN TISSUES; CD SPECTROSCOPIES; COUPLED RECEPTORS; CYCLIC PEPTIDES; G PROTEINS; HIGH RESOLUTIONS; ORTHOGONAL METHODOLOGIES; PHASE COUPLINGS; SIDE CHAINS; SPECIFIC BINDINGS; STRUCTURE DETERMINATIONS; SUBMICROMOLAR AFFINITIES; TURN STRUCTURES;

ACIDS; AMINATION; BINDING ENERGY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN; HYDROGEN BONDS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDES; PROTEINS; THREE DIMENSIONAL;

AMINES;

ALPHA AMINO ACID; BETA AMINO ACID; G PROTEIN COUPLED RECEPTOR; LYSINE; OCTREOTIDE; SOMATOSTATIN DERIVATIVE; SOMATOSTATIN RECEPTOR; TETRAPEPTIDE; TRYPTOPHAN;

ARTICLE; BINDING AFFINITY; BRAIN TISSUE; CIRCULAR DICHROISM; CYCLIZATION; DEPROTECTION REACTION; ENZYME ACTIVATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; LUNG PARENCHYMA; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN EXPRESSION; PROTEIN INTERACTION; PROTEIN PURIFICATION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 55549145024     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200890190     Document Type: Article

References (92)

1. K. Gademann, M. Ernst, D. Hoyer, D. Seebach, Angew. Chem., Int. Ed. 1999, 38, 1223.
2. K. Gademann, M. Ernst, D. Seebach, D. Hoyer, Helv. Chim. Acta 2000, 83, 16.
3. K. Gademann, T. Kimmerlin, D. Hoyer, D. Seebach, J. Med. Chem. 2001, 44, 2460.
4. D. Seebach, M. Rueping, P. I. Arvidsson, T. Kimmerlin, P. Micuch, C. Noti, D. Langenegger, D. Hoyer, Helv. Chim. Acta 2001, 84, 3503.
5. C. Nunn, M. Rueping, D. Langenegger, E. Schuepbach, T. Kimmerlin, P. Micuch, K. Hurth, D. Seebach, D. Hoyer, Naunyn-Schmiedebergs Arch. Pharmacol. 2003, 367, 95.
6. D. Seebach, L. Schaeffer, M. Brenner, D. Hoyer, Angew. Chem., Int. Ed. 2003, 42, 776.
7. H. Wiegand, B. Wirz, A. Schweitzer, G. Gross, M. I. R. Perez, H. Andres, T. Kimmerlin, M. Rueping, D. Seebach, Chem. Biodivers. 2004, 1, 1812.
8. D. Hoyer, G. I. Bell, M. Berelowitz, J. Epelbaum, W. Feniuk, P. P. A. Humphrey, A. M. Ocarroll, Y. C. Patel, A. Schonbrunn, J. E. Taylor, T. Reisine, Trends Pharmacol. Sci. 1995, 16, 86;
9. E. E. Muller, V. Locatelli, D. Cocchi, Physiol. Rev. 1999, 79, 511;
10. Z. Csaba, P. Dournaud, Neuropeptides 2001, 35, 1.
11. H. M. Weiss, B. Wirz, A. Schweitzer, R. Amstutz, M. I. R. Perez, H. Andres, Y. Metz, J. Gardiner, D. Seebach, Chem. Biodivers. 2007, 4, 1413.
12. W. Bauer, U. Briner, W. Doepfner, R. Haller, R. Huguenin, P. Marbach, T. J. Petcher, J. Pless, Life Sci. 1982, 31, 1133.
13. E. Pohl, A. Heine, G. M. Sheldrick, Z. Dauter, K. S. Wilson, J. Kallen, W. Huber, P. J. Pfaffli, Acta Crystallogr., Sect. D 1995, 51, 48.
14. C. R. R. Grace, J. Erchegyi, S. C. Koerber, J. C. Reubi, J. Rivier, R. Riek, J. Med. Chem. 2006, 49, 4487;
15. C. R. R. Grace, L. Durrer, S. C. Koerber, J. Erchegyi, J. C. Reubi, J. E. Rivier, R. Riek, J. Med. Chem. 2005, 48, 523;
16. C. R. R. Grace, S. C. Koerber, J. Erchegyi, J. C. Reubi, J. Rivier, R. Riek, J. Med. Chem. 2003, 46, 5606.
17. D. Seebach, B. Jaun, R. Sebesta, R. I. Mathad, O. Flögel, M. Limbach, H. Sellner, S. Cottens, Helv. Chim. Acta 2006, 89, 1801.
18. D. F. Hook, F. Gessier, C. Noti, P. Kast, D. Seebach, ChemBioChem 2004, 5, 691.
19. S. A. Kates, N. A. Solé, C. R. Johnson, D. Hudson, G. Barany, F. Albericio, Tetrahedron Lett. 1993, 34, 1549.
20. A. Trzeciak, W. Bannwarth, Tetrahedron Lett. 1992, 33, 4557.
21. a) J. A. Davies, Amino Acids, Peptides, Proteins 2001, 32, 287;
22. b) A. Janecka, M. Zubrzycka, T. Janecki, J. Pept. Res. 2001, 58, 91;
23. c) U. Schmidt, J. Langner, J. Pept. Res. 1997, 49, 67.
24. M. Rothe, D. Mühlhausen, Angew. Chem., Int. Ed. 1979, 18, 74.
25. D. Seebach, A. K. Beck, D. J. Bierbaum, Chem. Biodivers. 2004, 1, 1111.
26. P. W. Sutton, A. Bradley, J. Farràs, P. Romea, F. Urpí, J. Vilarrasa, Tetrahedron 2000, 56, 7947.
27. D. N. J. White, C. Morrow, P. J. Cox, C. N. C. Drey, J. Lowbridge, J. Chem. Soc., Perkin Trans. 2 1982, 239.
28. J. Lowbridge, E. Mtetwa, R. J. Ridge, C. N. C. Drey, J. Chem. Soc., Perkin Trans. 1 1986, 155.
29. D. Seebach, M. Overhand, F. N. M. Kühnle, B. Martinoni, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1996, 79, 913;
30. J. L. Matthews, M. Overhand, F. N. M. Kühnle, P. E. Ciceri, D. Seebach, Liebigs Ann./Recl. 1997, 1371;
31. J. L. Matthews, K. Gademann, B. Jaun, D. Seebach, J. Chem. Soc., Perkin Trans. 1 1998, 3331.
32. K. Gademann, D. Seebach, Helv. Chim. Acta 2001, 84, 2924.
33. F. Büttner, M. Erdélyi, P. I. Arvidsson, Helv. Chim. Acta 2004, 87, 2735.
34. F. Fujimura, M. Fukuda, J. Sugiyama, T. Morita, S. Kimura, Org. Biomol. Chem. 2006, 4, 1896.
35. S. Fournel, S. Wieckowski, W. Sun, N. Trouche, H. Dumortier, A. Bianco, O. Chaloin, M. Habib, J.-C. Peter, P. Schneider, B. Vray, R. E. Toes, R. Offringa, C. J. M. Melief, J. Hoebeke, G. Guichard, Nat. Chem. Biol. 2005, 1, 377;
36. M. Habib, M. N. Rivas, M. Chamekh, S. Wieckowski, W. Sun, A. Bianco, N. Trouche, O. Chaloin, H. Dumortier, M. Goldman, G. Guichard, S. Fournel, B. Vray, J. Immunol. 2007, 178, 6700.
37. a) D. Seebach, J. L. Matthews, A. Meden, T. Wessels, C. Baerlocher, L. B. McCusker, Helv. Chim. Acta 1997, 80, 173;
38. b) H. C. Le, T. Hintermann, T. Wessels, Z. Gan, D. Seebach, R. R. Ernst, Helv. Chim. Acta 2001, 84, 208.
39. T. D. Clark, L. K. Buehler, M. R. Ghadiri, J. Am. Chem. Soc. 1998, 120, 651.
40. M. Royo, J. Farrera-Sinfreu, L. Solé, F. Albericio, Tetrahedron Lett. 2002, 43, 2029.
41. F. Büttner, A. S. Norgren, S. Zhang, S. Prabpai, P. Kongsaeree, P. I. Arvidsson, Chem. - Eur. J. 2005, 11, 6145.
42. S. A. W. Gruner, V. Truffault, G. Voll, E. Locardi, M. Stöckle, H. Kessler, Chem. - Eur. J. 2002, 8, 4366.
43. F. Schumann, A. Müller, M. Koksch, G. Müller, N. Sewald, J. Am. Chem. Soc. 2000, 122, 12009;
44. M. Sukopp, R. Schwab, L. Marinelli, E. Biron, M. Heller, E. Várkondi, A. Pap, E. Novellino, G. Kéri, H. Kessler, J. Med. Chem. 2005, 48, 2916;
45. D. Zimmermann, E. W. Guthöhrlein, M. Malešević, K. Sewald, L. Wobbe, C. Heggemann, N. Sewald, ChemBioChem 2005, 6, 272;
46. A. S. Norgren, F. Büttner, S. Prabpai, P. Kongsaeree, P. I. Arvidsson, J. Org. Chem. 2006, 71, 6814.
47. a) M. Z. Magee, K. Hofmann, J. Am. Chem. Soc. 1949, 71, 1515;
48. b) J. C. Sheehan, W. L. Richardson, J. Am. Chem. Soc. 1954, 76, 6329;
49. c) R. Schwyzer, A. Tun-Kyi, Helv. Chim. Acta 1962, 45, 859;
50. d) H. Gerlach, J. A. Owtschinnikow, V. Prelog, Helv. Chim. Acta 1964, 47, 2294.
51. a) J. J. Wen, A. F. Spatola, Tetrahedron Lett. 2005, 46, 2499;
52. b) S. Ueda, S. Oishi, Z.-X. Wang, T. Araki, H. Tamamura, J. Cluzeau, H. Ohno, S. Kusano, H. Nakashima, J. O. Trent, S. C. Peiper, N. Fujii, J. Med. Chem. 2007, 50, 192.
53. U. Schmidt, H. Griesser, A. Lieberknecht, J. Talbiersky, Angew. Chem., Int. Ed. 1981, 20, 280;
54. b) U. Schmidt, A. Lieberknecht, H. Griesser, J. H\usler, Angew. Chem., Int. Ed. 1981, 20, 281;
55. c) U. Schmidt, A. Lieberknecht, J. Wild, Synthesis 1988, 159.
56. T. Jeremic, A. Linden, K. Moehle, H. Heimgartner, Tetrahedron 2005, 61, 1871.
57. S. F. Brady, R. M. Freidinger, W. J. Paleveda, C. D. Colton, C. F. Homnick, W. L. Whitter, P. Curley, R. F. Nutt, D. F. Veber, J. Org. Chem. 1987, 52, 764;
58. D. F. Veber, R. M. Freidinger, D. S. Perlow, W. J. Paleveda Jr., F. W. Holly, R. G. Strachan, R. F. Nutt, B. H. Arison, C. Homnick, W. C. Randall, M. S. Glitzer, R. Saperstein, R. Hirschmann, Nature 1981, 292, 55.
59. A. Patchornik, M. A. Kraus, Pure Appl. Chem. 1975, 43, 503;
60. A. Patchornik, 'Polymer Supported Reagents', in 'Modern Synthetic Methods 1976, Vol. 1', Ed. R. Scheffold, Sauerländer AG, Aarau, 1976, pp. 113-172.
61. W. F. DeGrado, E. T. Kaiser, J. Org. Chem. 1980, 45, 1295.
62. G. ]sapay, A. Profit, J. W. Taylor, Tetrahedron Lett. 1990, 31, 6121.
63. H. Mihara, S. Yamabe, T. Niidome, H. Aoyagi, H. Kumagai, Tetrahedron Lett. 1995, 36, 4837, and other refs. by the Mihara groupcited therein.
64. G. W. Kenner, J. R. McDermot, R. C. Sheppard, J. Chem. Soc., Chem. Commun. 1971, 636;
65. B. J. Backes, J. A. Ellman, J. Org. Chem. 1999, 64, 2322.
66. L. Yang, G. Morriello, Tetrahedron Lett. 1999, 40, 8197;
67. T. D. Clark, M. Sastry, C. Brown, G. Wagner, Tetrahedron 2006, 62, 9533.
68. L. S. Richter, J. Y. K. Tom, J. P. Burnier, Tetrahedron Lett. 1994, 35, 5547.
69. D. A. Annis, O. Helluin, E. N. Jacobsen, Angew. Chem., Int. Ed. 1998, 37, 1907;
70. M. Royo, J. Farrera-Sinfreu, L. Solé, F. Albericio, Tetrahedron Lett. 2002, 43, 2029;
71. J. T. Lundquist, J. C. Pelletier, Org. Lett. 2002, 4, 3219;
72. S. J. Reyes, K. Burgess, Tetrahedron: Asymmetry 2005, 16, 1061.
73. R. I. Mathad, B. Jaun, O. Flögel, J. Gardiner, M. Löweneck, J. D. C. Codée, P. H. Seeberger, D. Seebach, M. K. Edmonds, F. H. M. Graichen, A. D. Abell, Helv. Chim. Acta 2007, 90, 2251.
74. G. Lelais, D. Seebach, B. Jaun, R. I. Mathad, O. Flögel, F. Rossi, M. Campo, A. Wortmann, Helv. Chim. Acta 2006, 89, 361.
75. M. Rueping, ETH Diss. No. 14677, ETH-Zürich, 2002.
76. G. P. Dado, S. H. Gellman, J. Am. Chem. Soc. 1994, 116, 1054.
77. G. Melacini, Q. Zhu, M. Goodman, Biochemistry 1997, 36, 1233;
78. T. Hintermann, K. Gademann, B. Jaun, D. Seebach, Helv. Chim. Acta 1998, 81, 983.
79. S. Siehler, K. Seuwen, D. Hoyer, Naunyn-Schmiedebergs Arch. Pharmacol. 1998, 357, 483;
80. S. Siehler, K. Seuwen, D. Hoyer, Naunyn-Schmiedebergs Arch. Pharmacol. 1999, 360, 488.
81. J. Gardiner, D. Langenegger, D. Hoyer, A. K. Beck, R. I. Mathad, D. Seebach, Chem. Biodivers. 2008, 5, 1213.
82. T. Kimmerlin, ETH Diss. No. 14677, ETH Zürich, 2002.
83. J. D. A. Tyndall, B. Pfeiffer, G. Abbenante, D. P. Fairlie, Chem. Rev. 2005, 105, 793.
84. P. Micuch, D. Seebach, in 'Peptides: The Wave of the Future', Eds. M. Lebl, R. A. Houghten, American Peptide Society, San Diego, 2001, pp. 32-33;
85. P. Micuch, D. Seebach, Helv. Chim. Acta 2002, 85, 1567.
86. F. Gessier, L. Schaeffer, T. Kimmerlin, O. Flögel, D. Seebach, Helv. Chim. Acta 2005, 88, 2235.
87. 'Fmoc Solid Phase Peptide Synthesis: A Practical Approach', Vol. 222, Eds. W. C. Chang and P. D. White, Oxford University Press, Oxford, 2000.
88. W. S. Hancock, J. E. Battersby, Anal. Biochem. 1976, 71, 260.
89. T. D. Goddard, D. G. Kneller, 'program SPARKY v3.110', University of California, San Francisco, 2004.
90. C. D. Schwieters, J. J. Kuszewski, N. Tjandra, G. M. Clore, J. Magn. Reson. 2003, 160, 65.
91. E. G. Stein, L. M. Rice, A. T. Br-nger, J. Magn. Reson. 1997, 124, 154.
92. J. Gardiner, A. V. Thomae, R. I. Mathad, D. Seebach, S. D. Krämer, Chem. Biodivers. 2006, 3, 1181.