Carboxylate binding by guanidiniocarbonyl pyrroles: From self-assembly to peptide receptors

Current Organic Chemistry

Volumn 7, Issue 14, 2003, Pages 1485-1502

  Schmuck, Carsten ^a   Geiger, Lars ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; AMPHOLYTE; CARBOXYLIC ACID DERIVATIVE; CATION; DIMER; GUANIDINIOCARBONYLPYRROLE DERIVATIVE; OLIGOMER; OLIGOPEPTIDE; PEPTIDE; PYRROLE DERIVATIVE; RECEPTOR; SOLVENT; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; BINDING KINETICS; COMBINATORIAL LIBRARY; COMPARATIVE STUDY; HUMAN; MASS SPECTROMETER; MOLECULAR MODEL; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE; PROTEIN ASSEMBLY; PROTEIN MOTIF; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; THERMODYNAMICS; X RAY;

EID: 0043195552     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272033486387     Document Type: Article

References (190)

1. Schneider, H.-J.; Yatsimirsky, A. Principles and Methods in Supramolecular Chemistry, VCH: Weinheim, 2000.
2. Steed, J. W.; Atwood, J. L. Supramolecular Chemistry, Wiley: Chichester, 2000.
3. Lehn, J.-M. Supramolecular Chemistry; Concepts and Perspectives, VCH: Weinheim 1995.
4. Vögtle, F. Supramolekulare Chemie, Teubner: Stuttgart, 1992.
5. Vögtle, F. Cyclophan Chemie, Teubner: Stuttgart, 1990.
6. Philp, D.; Stoddart, J.F. Angew. Chem. 1996, 108, 1242-1286;
7. Angew. Chem. Int. Ed. Engl. 1996., 35, 1154-1196.
8. Whitesides, G. M.; Mathias, J.P.; Seto, C. T. Science 1991, 254, 1312-1319.
9. Lehn, J.-M. PNAS 2002, 9, 4763-4768.
10. Whitesides, G. M.; Boncheva, M. PNAS 2002, 9, 4769-4774.
11. Menger, F.M.; PNAS 2002, 9, 4818-4822.
12. Rouvray, D. Chemistry in Britain 2000, 121, 26-29.
13. Bishop, R. Synlett 1999, 1351-1359.
14. Weber, E. Design of Organic Solids, Top. Curr. Chem. 1998, 198.
15. Desiraju, G. R. Angew. Chem. 1995, 107, 2540-2558;
16. Angew. Chem. Int. Ed. Engl. 1995, 34, 2328-2345.
17. Desiraju, G. R. Crystal Engineering: The Design of Organic Solids, Elsevier: New York, 1989.
18. Wright, J. D. Molecular Crystals, Cambridge University Press: Cambridge 1987.
19. Chin, D. N.; Palmore, T. R.; Whitesides, G. M. J. Am. Chem. Soc. 1999, 121, 2115-2132.
20. MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 194, 94, 2383-2420.
21. Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37-44.
22. Sherrington, D. C.; Taskinen, K. A. Chem. Soc. Rev. 2001, 30, 83-93.
23. Zimmermann, S. C.; Corbin, P. S. Struct. Bond. 2000, 96, 63-94.
24. Schmuck, C.; Wienand, W. Angew. Chem. 2001, 113, 4493-4499;
25. Angew. Chem. Int. Ed. Engl. 2001, 40, 4363-4369.
26. Schalley, C. A.; Rebek, Jr. J. Chemical Encapsulation in Self-Assembling Capsules in Stimulating Concepts in Chemistry; Ed.; Vögtle, F.; Stoddart, J. F.; Shibasaki, M., Wiley-VCH: Weinheim, 2000, 199-200.
27. Rebek, Jr. J. Acc. Chem. Res. 1999, 32, 278-286.
28. Conn, M. M.; Rebek, Jr. J. Chem. Rev. 1997, 97, 1647-1668.
29. Seeman, N. C. Angew. Chem. 1998, 110, 3408-3428;
30. Angew. Chem. Int. Ed. Engl. 1998, 37, 3220-3238.
31. Yanker, B. A. Neuron 1996, 16, 921-932.
32. Lansbury, Jr., P. T. Acc. Chem. Res. 1996, 29, 317-321.
33. Selkoe, D. J. Science 1997, 275, 630-631.
34. Gopinath, L. Chem. Brit. 1998, 38-40.
35. Austen, B.; Manca, M. Chem. Brit. 2000, 28-31.
36. Baumeister, R.; Eimer, S. Angew. Chem. 1998, 110, 3148-3152;
37. Angew. Chem. Int. Ed. Engl. 1998, 37, 3148-3152.
38. Hardy, J.; Selkoe, D. J. Science 2002, 297, 353-356.
39. Edenhofer, F.; Weiss, S.; Winnacker, E.-L.; Famulok, M. Angew. Chem. 111, 1748-1770;
40. Angew. Chem. Int. Ed. Engl. 1997, 36, 1674-1694.
41. Klug, A. Angew. Chem. 1983, 95, 579-596;
42. Angew. Chem. Int. Ed. Engl. 1983, 22, 565-582.
43. Alberts, B.; Bray, D.; Lewis, J.; Raff, M.; Roberts, K.; Watson, J.D. Molecular Biology of the Cell, Garland Publishing, Inc.: New York & London, 1994.
44. Gellman, S.H. Chem. Rev. 1997, 97, 1231-1232.
45. Horvath, P.; Gergely, A.; Noszal, B. J. Chem. Soc. Perkin Trans. 1 1996, 1419-1422
46. Kelly, T.R.; Kim, M.H. J. Am. Chem. Soc. 1994, 116, 7072-7080.
47. Ariga, K.; Anslyn, E.V. J. Org. Chem. 1992, 57, 417-419.
48. Breslow, R.; Yang, Z.; Ching, R.; Trojandt, G.; Odobel, F. J. Am. Chem. Soc. 1998, 120, 3536-3537.
49. Peczuh, M. W.; Hamilton, A.D.; Sanchez-Qesada, J.; De Mendoza, J.; Haak, T.; Giralt, E. J. Am. Chem. Soc. 1997, 119, 9327-9328.
50. Berger, M.; Schmidtchen, F. P. J. Am. Chem. Soc. 1996, 118, 8947-8948.
51. Fan, E.; Van Arman, S.A.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369-370.
52. Schießl, P.; Schmidtchen, F. P. Tetrahedron Lett. 1993, 2449-2452.
53. Furuta, H.; Magda, D.; Sessler, J. L. J. Am. Chem. Soc. 1991, 113, 978-985.
54. Kelly-Rowley, A. M.; Cabell, L. A.; Anslyn, E. V. J. Am. Chem. Soc. 1991, 113, 9687-9688.
55. Constant, J. F.; Fahy, J.; Lhomme, J. Tetrahedron Lett. 1987, 1777-1780.
56. Schmuck, C. Chem. Eur. J. 2000, 6, 709-718.
57. Fitzmaurice, R. J.; Kyne, G. M.; Douheret, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1, 1, 2002, 841-864.
58. Beer, P. D.; Gale, P. A. Angew. Chem. 2001, 113, 502-532;
59. Beer, P. D.; Gale, P. A. Angew. Chem. Int. Ed. Engl. 2001, 40, 486-517.
60. Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646.
61. Bianchi, A.; Bowman-James, K.; García-España, E. Supramolecular Chemistry of Anions, Wiley-VCH: New York, 1997.
62. Galán, A.; DeMendoza, J. Top. Curr. Chem. 1995, 175.
63. Ptashne, M.; Gann, A. Nature, 1997, 386, 569.
64. Knieps, S.; Martin, C. M.; Dove, S.; Buschaure, A. Bioorg. Med. Chem. Lett. 1995, 5, 2065-2070.
65. Dietrich, B.; Fyles, T. M.; Lehn, J. M.; Pease, L. G.; Fyles, D. L. J. Chem. Soc. Chem., Commun. 1978, 934-936.
66. Müller, G.; Riede, J.; Schmidtchen, F. P. Angew. Chem. 1988, 100, 1574-1575.
67. Dixon, R. D.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1992, 114, 365-366.
68. Ariga, K.; Anslyn, E. V. J. Org. Chem. 1992, 57, 417-419.
69. Schiessl, P.; Schmidtchen, F. P. J. Org. Chem. 1994, 59, 509-511.
70. Stephan, H.; Gloe, K.; Schiessl, P.; Schmidtchen, F. P. Supramol. Chem. 1995, 5, 273-280.
71. Schiessl, P.; Schmidtchen, F. P. Tetrahedron Lett. 1993, 34, 2449-2452.
72. Lavigne, J. J.; Anslyn, E. V. Angew. Chem. 1999, 111, 3903-3906
73. Angew. Chem. Int. Ed. Engl. 1999, 38, 3666-3669.
74. Berger, M.; Schmidtchen, F. P. Angew. Chem. 1998, 110, 2840-2842;
75. Angew. Chem. Int. Ed. Engl. 1998, 37, 2694-2696.
76. Jagessar, R. C.; Shang, M.; Scheldt, W. R.; Burns, D. H. J. Am. Chem. Soc. 1998, 120, 11684-11692.
77. Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533-8534.
78. Buhlmann, P.; Nishizawa, S.; Xiao, K. P.; Umewaza, Y. Tetrahedron 1997, 53, 1647-1654.
79. Berger, M.; Schmidtchen, F. P. J. Am. Chem. Soc. 1996, 118, 8947-8948.
80. Kato, Y.; Conn, M. M.; Rebek Jr., J. J. Am. Chem. Soc. 1994, 116, 3279-3284.
81. Fan, E.; Anslyn, E. V. J. Am. Chem. Soc. 1993, 115, 10042-10055.
82. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufiled, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
83. Zheng, Y. J.; Ornstein, R. L. J. Am. Chem. Soc. 1996, 118, 11237-11243.
84. Dietrich, B.; Fyles, D. L.; Fyles, T. M.; Lehn, J.-M. Helv. Chim. Acta 1979, 62, 2763-2787.
85. Schmuck, C. Eur. J. Org. Chem. 1999, 2397-2403.
86. Schmuck, C.; Wienand, W. J. Am. Chem. Soc. 2003, 125, 452-459.
87. Harbuck, J. W.; Rapoport, H. J. Org. Chem. 1972, 37, 3618-3621.
88. Silverstein, R. M.; Ryskiewicz, E. E.; Willard, C. Org. Synth. Coll. Vol. IV, 1963, 831-833.
89. Barker, P.; Gendler, P.; Rapoport, H. J. Org. Chem. 1978, 43, 4849-4853.
90. Bicking, J. B.; Robb, C. M.; Kwong, S. F.; Cragoe, E. J. J. Med. Chem. 1967, 10, 598-602.
91. Zapf, C. W.; Creighton, C. J.; Tomioka, M.; Goodman, M. Org. Lett. 2001, 3, 1133-1136.
92. Noss, L.; Liddell, P. A.; Moore, A. L.; Moore, T. A.; Gust, D. J. Phys. Chem. B 1997, 101, 458-456.
93. Schmuck, C.; Lex, J. Eur. J. Org. Chem. 2001, 1519-1523.
94. Schmuck, C.; Lex, J. Org. Lett. 1999, 1, 1779-1781.
95. Connors, K. A. Binding Constants, Wiley: New York, 1987.
96. Davies, M.; Bonnat, M.; Guillier, F.; Kilburn, J. D.; Bradley, M.; J. Org. Chem. 1998, 63, 8696-8703.
97. Storey, B. T.; Sullivan, W. W.; Moyer, C. L. J. Org. Chem. 1964, 29, 3118-3120.
98. Kang, J.; Rebek Jr., J. Nature 1997, 385, 50-52.
99. Kang, J.; Rebek Jr., J. Nature 1996, 382, 239-241.
100. Meissner, R. S.; DeMendoza, J.; Rebek Jr., J. Science 1995, 270, 1485-1488.
101. Rebek Jr., J. Acc. Chem. Res. 1999, 32, 278-286.
102. Conn, M. M.; Rebek Jr., J. Chem. Rev. 1997, 97, 1647-1668.
103. MacDonald, C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420.
104. Zimmermann, S. C.; Corbin, P. S. Struct. Bond. 2000, 63-94.
105. Sessler, J. L.; Wang, R. Angew. Chem. 1998, 110, 1818-1821;
106. Angew. Chem. Int. Ed. Engl. 1998, 37, 1726-1729.
107. Hirschberg, J. J. H. K.; Brunsveld, L.; Ramzi, A.; Vekemans, J. A. J. M.; Sijbesma, R. P.; Meijer, E. W. Nature 2000, 407, 167-170.
108. Soentjens, S. H. M.; Sijbesma, R. P.; Van Genderen, M. H. P.; Meijer, E. W. J. Am. Chem. Soc. 2000, 122, 7487-7493.
109. Beijer, F. H. Kooijman, H.; Spek, A. L.; Sijbesma, R.; Meijer, E. W. Angew. Chem. 1998, 110, 79-82;
110. Angew. Chem. Int. Ed. Engl. 1998, 37, 75-78.
111. Sijbesma, R. P.; Beijer, F. H.; Brunsvald, L.; Folmer, B. J. B.; Hirschberg, J. J. H. K.; Lange, R. F. M.; Lowe, J. K. L.; Meijer, E. W. Science 1997, 278, 1601-1604.
112. Cabezon, B.; Cao, J.; Raymo, F. M.; Stoddart, J. F.; White A. J. P.; Williams, D. J. Angew. Chem. 2000, 112, 152-155;
113. Angew. Chem. Int. Ed. Engl. 2000, 39, 148-151.
114. Ashton, P. R.; Parson, I. W.; Raymo, F. M.; Stoddart, J. F.; White, A.J.P.; Williams, D. J.; Wolf, R. Angew. Chem. 1998, 110, 2016-2019;
115. Angew. Chem. Int. Ed. Engl. 1998, 37, 1913-1916.
116. Yamaguchi, N.; Gibson, H. W. Angew. Chem. 1999, 111, 195-199;
117. Angew. Chem. Int. Ed. Engl. 1999, 38, 143-147.
118. Yamaguchi, N.; Nagvekar, D. S.; Gibson, H. W. Angew. Chem. 1998, 110, 2518-2520;
119. Angew. Chem. Int. Ed. Engl. 1998, 37, 2361-2364.
120. Fujita, M. Chem. Soc. Rev. 1998, 27, 417-426.
121. Stang, P. J. Chem. Eur. J. 1998, 4, 19-27.
122. Linton, B.; Hamilton, A. D. Chem. Rev. 1997, 97, 1669-1681.
123. Stang, P. J.; Olenyuk, B. Acc. Chem. Res. 1997, 30, 502-518.
124. MacGillivray, L. R.; Atwood, J. L. Angew. Chem. 1999, 111, 1080-1096.
125. Grawe, T.; Schrader, T.; Gurrath, M.; Kraft, A.; Osterod, F. Org. Lett. 2000, 2, 29-32.
126. Corbellini, F.; Fiammengo, R.; Timmermann, P.; Crego-Calama, M.; Versluis, K.; Heck, A. J. R.; Lyten, I.; Rheinhoudt, D. N. J. Am. Chem. Soc. 2002, 124, 6569-6575.
127. Apella, D. H.; Barchi Jr., J. J.; Durell, S. R.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 2309-2310.
128. Seebach, D.; Abele, S.; Gademann, K.; Jaun, B. Angew. Chem. 1999, 111, 1700-1702;
129. Angew. Chem. Int. Ed. Engl. 1999, 38, 1595-1597.
130. Blanco, F.; Ramirez-Alvarado, M.; Serrano, L. Curr. Opin. Struct. Biol. 1998, 8, 107-111.
131. Koert, U. Angew. Chem. 2001, 11, 2137-2140;
132. Angew. Chem. Int. Ed. Engl. 2001, 40, 2076-2078.
133. Sutor, D. J. Nature 1962, 195, 68-69.
134. Desijaru, G. R.; Steiner, T. The Weak Hydrogen Bonds in Structural Chemistry and Biology, Oxford University Press: Oxford 1999.
135. Steiner, T. Chem. Commun. 1997, 727-734.
136. Desijaru, G. R. Acc. Chem. Res. 1996, 29, 441-449.
137. Desijaru, G. R. Acc. Chem. Res. 1991, 24, 290-296.
138. Kool, E. T.; Morales, J. C.; Guckian, K. M. Angew. Chem. 2000, 112, 1046-1068;
139. Angew. Chem. Int. Ed. Engl. 2000, 39, 990-1009.
140. Kool, E. T. Chem. Rev. 1997, 97, 1473-1487.
141. Ribeiro-Claro, P. J. A.; Marques, M. P. M.; Amado, A. M. Chem. Phys. Chem., 2002, 3, 599-606.
142. Schmuck, C. Tetrahedron 2001, 57, 3063-3067.
143. Davis Jr., J.C.; Deb, K. K. Adv. Magn. Res. 1970, 4, 201-270.
144. Bangerter, B. W.; Chan, S. I. J. Am. Chem. Soc. 1969, 91, 3910-3921.
145. LaPlanche, L. A.; Thompson, H. B.; Rogers, M. T. J. Phys. Chem. 1965, 69, 1482-1488.
146. Sebo, L.; Schweizer, B.; Diedrich, F. Helv. Chim. Acta 2000, 83, 80-92.
147. Linton, B.; Hamilton, A. D. Tetrahedron 1999, 55, 6027-6038.
148. Berger, M.; Schmidtchen, F. P. J. Am. Chem. Soc. 1999, 121, 9986-9993.
149. Meissner, R.; Garcias, X.; Mecozzi, S.; Rebek Jr., J. J. Am. Chem. Soc. 1997, 119, 77-85.
150. Schmuck, C. J. Org. Chem. 2000, 65, 2432-2437.
151. Pons, J.-F., Fauchère, J.-L., Lamaty, F., Molla, A., Lazaro, R., Eur. J. Org. Chem. 1998, 853-859.
152. Nowick, J. S. Acc. Chem. Res. 1999, 32, 287-296.
153. Gellman, S.H. Acc. Chem. Res. 1998, 31, 173-180.
154. Nowick, J. S.; Smith, E. M., Pairish, M. Chem. Soc. Rev. 1996, 401-415.
155. Schneider, J. P.; Kelly, J. W. Chem. Rev. 1995, 95, 2169-2187.
156. Nowick, J. S.; Chung, D. M.; Maitra, K.; Maitra, S.; Stigers, K. D.; Sun, Y. J. Am. Chem. Soc. 2000, 122, 7654-7661.
157. Junquera, E.; Nowick, J. S. J. Org. Chem. 1999, 64, 2527-2531.
158. Schmuck, C.; Heil, M. Org. Lett. 2001, 3, 1253-1256.
159. Davis, A.M.; Teague, S.J. Angew. Chem. 1999, 111, 778-792;
160. Angew. Chem. Int. Ed. Engl. 1999, 38, 736-749.
161. Williams, D.H.; Westwell, M. S.; Chem. Soc. Rev. 1998, 27, 57-64.
162. Lahiri, S.; Thompson, J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315-11319.
163. Sirish, M.; Schneider, H.-J. J. Am. Chem. Soc. 2000, 122, 5881-5882.
164. Guckian, K. M.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 2000, 122, 2213-2222.
165. Houk, K. N.; Menzer, S.; Newton, S. P.; Raymo, F. M; Stoddart, J. F.; Williams, D. J. J. Am. Chem. Soc. 1999, 121, 1479-1487.
166. Nicolaou, K. C.; Boddy, C. N. C.; Bräse, S.; Wissinger, N. Angew. Chem. 1999, 111, 2230-2287;
167. Angew. Chem. Int. Ed. Engl. 1999, 38, 2096-2152.
168. Williams, D. H.; Bardesley, B.; Angew. Chem. 1999, 111, 1264-1286;
169. Angew. Chem. Int. Ed. Engl. 1999, 38, 1172-1193.
170. Walsh, C. Science 1999, 284, 442-443.
171. Williams, D. H. Nat. Prod. Rep. 1996, 469-477.
172. Wittinghofer, A.; Waldmann, H. Angew. Chem. 2000, 112, 4360-4383.
173. Angew. Chem. Int. Ed. Engl. 2000, 39, 4192-4214.
174. Cavenee, W. K.; White, R. L. Spektrum der Wissenschaft 1995, 5, 36-45.
175. Krause, G. Signalübertragung durch Ras-Proteine in Biochemie der Regulation und Signalübertragung, Wiley-VCH: Weinheim, 1997, 328.
176. Hinterding, K.; Alonso-Díaz, D.; Waldmann, H. Angew. Chem., 1998, 110, 716-780;
177. Angew. Chem. Int. Ed. Engl. 1998, 37, 688-749.
178. Bell, T. W.; Khasanov, A.B.; Drew, M. G. B.; Filikov, A.; James, T. L. Angew. Chem. 1999, 111, 2705-2709;
179. Angew. Chem. Int. Ed. Engl. 1999, 38, 2543-2547.
180. Hossain, A.; Schneider, H.-J. J. Am. Chem. Soc. 1998, 120, 11208-11209.
181. Breslow, R.; Yang, Z.; Ching, R.; Trojandt, G.; Odobel, F. J. Am. Chem. Soc. 1998, 120, 3536-3537.
182. Maletic, M., Wennemers, H.; McDonald, D. Q.; Breslow, R.; Still, W. C. Angew. Chem. 1996, 108, 1594-1596;
183. Angew. Chem. Int. Ed. Engl. 1996, 35, 1490-1492.
184. LaBrenz, S.R.; Kelly, J. W. J. Am. Chem. Soc. 1995, 117, 1655-1656.
185. Albert, J.S.; Goodman, M. S.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 1143-1144.
186. Wennemers, H.; Still, W. C. Tetrahedron Lett. 1994, 35, 6413-6416.
187. Schmuck, C. Chem. Commun. 1999, 843-844.
188. Schrader, T. H. Tetrahedron Lett. 1998, 39, 57-520.
189. Dougherty, D. A. Science 1996, 271, 163-167.
190. Schmuck, C.; Heil, M. Org. Biomol. Chem. 2003, 1, 633-636.