How to improve guanidinium cations for oxoanion binding in aqueous solution?. The design of artificial peptide receptors

Coordination Chemistry Reviews

Volumn 250, Issue 23-24, 2006, Pages 3053-3067

  Schmuck, Carsten ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Carboxylate receptors; Guanidinium cations; Molecular recognition; Self assembly; Supramolecular chemistry

Indexed keywords

EID: 33750498924     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2006.04.001     Document Type: Review

References (174)

1. Hannon C.L., and Anslyn E.V. Bioorg. Chem. Front. 3 (1993) 193
2. Piatek A.M., Gray M., and Anslyn E.V. J. Am. Chem. Soc. 126 (2004) 9878
3. Zepik H.H., and Benner S.A. J. Org. Chem. 64 (1999) 8080
4. For comprehensive reviews of anion recognition see the following
5. Schug K.A., and Lindner W. Chem. Rev. 105 (2005) 67
6. Best M.D., Tobey S.L., and Anslyn E.V. Coord. Chem. Rev. 240 (2003) 3
7. Gale P.A. Coord. Chem. Rev. 240 (2003) 191
8. Fitzmaurice R.J., Kyne G.M., Douheret D., and Kilburn J.D. J. Chem. Soc., Perkin Trans. 1 (2002) 841
9. Snowden T.S., and Anslyn E.V. Curr. Opin. Chem. Biol. 3 (1999) 740
10. Beer P.D., and Schmitt P. Curr. Opin. Chem. Biol. 1 (1997) 475
11. Bianchi A., Bowman-James K., and Garcia-España E. Supramolecular Chemistry of Anions (1997), Wiley/VCH, New York
12. Schmidtchen F.P., and Berger M. Chem. Rev. 97 (1997) 1609
13. Seel C., Galán A., and deMendoza J. Top. Curr. Chem. 175 (1995) 101
14. Meot-Ner M. Chem. Rev. 105 (2005) 213
15. For example, Fersht has estimated that charge interactions within proteins are much stronger than those in free solution
16. Fersht A.R. Trends Biochem. Sci. 12 (1987) 301
17. Fersht A.R., Shi J.P., Knill-Jones J., Lowe D.M., Wilkinson A.J., Blow D.M., Brick P., Carter P., Waye M.M., and Winter G. Nature 314 (1985) 235
18. Peterlin-Masic L., and Kikelj D. Tetrahedron 57 (2001) 7073
19. Schmuck C., and Geiger L. Curr. Org. Chem. 7 (2003) 1485
20. Some recent examples
21. Schmidtchen F.P. Org. Lett. 3 (2002) 431
22. Haj-Zaroubi M., Mitzel N.W., and Schmidtchen F.P. Angew. Chem. Int. Ed. 41 (2002) 104
23. Sebo L., Schweizer B., and Diederich F. Helv. Chim. Acta 83 (2000) 80
24. Some selected examples can be found in
25. Cannizzaro C.E., and Houk K.N. J. Am. Chem. Soc. 124 (2002) 7163
26. Raymo F.M., Bartberger M.D., Houk K.N., and Stoddart J.F. J. Am. Chem. Soc. 123 (2001) 9264
27. Houk K.N., Menzer S., Newton S.P., Raymo F.M., Stoddart J.F., and Williams D.J. J. Am. Chem. Soc. 121 (1999) 1479
28. Brown S.P., Schaller T., Seelbach U.P., Koziol F., Ochsenfeld C., Klärner F.-G., and Spiess H.W. Angew. Chem. Int. Ed. 40 (2001) 717
29. Kamieth M., Klärner F.-G., and Diederich F. Angew. Chem. Int. Ed. 37 (1998) 3303
30. Ma J.C., and Dougherty D.A. Chem. Rev. 97 (1997) 1303
31. Gallivan J.P., and Dougherty D.A. J. Am. Chem. Soc. 122 (2000) 870
32. Mangani S., and Ferraroni M. In: Bianchi A., Bowman-James K., and Garcia-Espana E. (Eds). Supramolecular Chemistry of Anions (1997), Wiley/VCH, New York 63
33. Horvath P., Gergely A., and Noszal B. J. Chem. Soc., Perkin Trans. 2 (1996) 1419
34. Hossain M.A., and Schneider H.-J. Chem. Eur. J. 5 (1999) 1284
35. Schneider H.-J. Chem. Soc. Rev. 22 (1994) 227
36. Jeffrey G.A. An Introduction to Hydrogen Bonding (1997), Oxford University Press, New York
37. Israelachvili J. Intermolecular & Surface Forces. second ed. (1992), Academic Press, London
38. Prins L.-J., Reinhoudt D.N., and Timmerman P. Angew. Chem. Int. Ed. 40 (2001) 2383
39. In contrast to Coulomb interactions between two point charges which are of course non-directional, charge interactions with organic molecules such as guanidinium cations are directional. This can be due to the formation of H-bond enforced ion pairs and/or the anisotropic solvation of such ions
40. Mason P.E., Neilson G.W., Enderby J.E., Saboungi M.-L., Dempsey C.E., MacKerell Jr. A.D., and Brady J.W. J. Am. Chem. Soc. 126 (2004) 11462
41. For a general discussion of the directionality of non-covalent interactions see:. Glusker J.P. Top. Curr. Chem. 198 (1998) 1
42. For reviews on hydrophobic interactions see
43. Widom B., Bhimalapuram P., and Koga K. Phys. Chem. Chem. Phys. 5 (2003) 3085
44. Pratt L.R., and Pohorille A. Chem. Rev. 102 (2002) 2671
45. Southall N.T., Dill K.A., and Haymet A.D.J. J. Phys. Chem. B 106 (2002) 521
46. For reviews on aromatic interactions within peptides and in supramolecular model systems see
47. Waters M.L. Biopolymers 76 (2004) 435
48. Waters M.L. Curr. Opin. Chem. Biol. 6 (2002) 736
49. Hunter C.A., Lawson K.R., Perkins J., and Urch C.J. J. Chem. Soc., Perkin Trans. 2 (2001) 651
50. Burley S.K., and Petsko G.A. Science 229 (1985) 23
51. For a critical comment see:. Chung D.M., Dou Y., Baldi P., and Nowick J.S. J. Am. Chem. Soc. 127 (2005) 9998
52. Dietrich B., Fyles T.M., Lehn J.M., Pease L.G., and Fyles D.L. J. Chem. Soc., Chem. Commun. (1978) 934
53. Müller G., Riede J., and Schmidtchen F.P. Angew. Chem. 100 (1988) 1574
54. Dixon R.D., Geib J.S., and Hamilton A.D. J. Am. Chem. Soc. 114 (1992) 365
55. Ariga K., and Anslyn E.V. J. Org. Chem. 57 (1992) 417
56. Schiessl P., and Schmidtchen F.P. J. Org. Chem. 59 (1994) 509
57. Metzger A., Lynch V.M., and Anslyn E.V. Angew. Chem. Int. Ed. Engl. 36 (1997) 862
58. Schmuck C. Chem. Commun. (1999) 843
59. Schmuck C. Chem. Eur. J. 6 (2000) 709
60. Schmuck C. J. Org. Chem. 65 (2000) 2432
61. Schmuck C., and Heil M. Org. Lett. 3 (2001) 1253
62. Schmuck C., and Geiger L. Chem. Commun. (2004) 1698
63. Schmuck C., and Schwegmann M. J. Am. Chem. Soc. 127 (2005) 3373
64. Schmuck C., and Schwegmann M. Org. Biomol. Chem. 4 (2006) 836
65. Schmuck C., and Machon U. Chem. Eur. J. 11 (2005) 1109
66. For similar conclusions in different systems see
67. Kavallieratos K., Bertao C.M., and Crabtree R.H. J. Org. Chem. 64 (1999) 1675
68. Kyne G.M., Light M.E., Hursthouse M.B., deMendoza J., and Kilburn J.D. J. Chem. Soc., Perkin Trans. 1 (2001) 1258
69. Chang S.-Y., Kim H.S., Chang K.-J., and Jeong K.-S. Org. Lett. 6 (2004) 181
70. Adams H., Carver F.J., Hunter C.A., Morales J.C., and Seward E.M. Angew. Chem. Int. Ed. 35 (1996) 1542
71. Carver F.J., Hunter C.A., Jones P.S., Livingstone D.J., McCabe J.F., Seward E.M., Tiger P., and Spey S.E. Chem. Eur. J. 7 (2001) 4854
72. Schmuck C., and Wienand W. J. Am. Chem. Soc. 125 (2003) 452
73. For work on capsule formation in polar solvents based on the hetero association of oppositely charged ions see, e.g.
74. Grawe T., Schrader T., Zadmard R., and Kraft A. J. Org. Chem. 67 (2002) 3755
75. Corbellini F., Flammengo R., Timmerman P., Crego-Calama M., Veslius K., Heck A.J.R., Luyten I., and Reinhoudt D.N. J. Am. Chem. Soc. 124 (2002) 65969
76. Fiammengo R., Timmerman P., de Jong F., and Reinhoudt D.N. Chem. Commun. (2000) 2313
77. Hamilin B., Jullien L., Derouet C., Hervé du Penhoat C., and Berthault P. J. Am. Chem. Soc. 120 (1998) 8438
78. Bok Lee S., and Hong J.-I. Tetrahedron Lett. 37 (1996) 8501
79. Schmuck C., and Graupner S. Tetrahedron Lett. 46 (2005) 1295
80. For examples of endothermic binding in supramolecular systems see
81. Schmuck C. Tetrahedron 57 (2001) 3063
82. Sebo L., Schweizer B., and Diedrich F. Helv. Chim. Acta 83 (2000) 80
83. Linton B., and Hamilton A.D. Tetrahedron 55 (1999) 6027
84. Berger M., and Schmidtchen F.P. J. Am. Chem. Soc. 121 (1999) 9986
85. Berger M., and Schmidtchen F.P. Angew. Chem. Int. Ed. Engl. 37 (1998) 2694
86. Meissner R., Garcias X., Mecozzi S., and Rebek Jr. J. J. Am. Chem. Soc. 119 (1997) 77
87. Jorgensen W.L., and Pranata J. J. Am. Chem. Soc. 112 (1990) 2008
88. Pranata J., Wierschke S.G., and Jorgensen W.L. J. Am. Chem. Soc. 113 (1991) 2810
89. Jorgensen W.L., and Severance D.L. J. Am. Chem. Soc. 113 (1991) 209
90. Lukin O., and Leszczynski J. J. Phys. Chem. A 106 (2002) 6775
91. Lukin O., and Leszczynski J. J. Phys. Chem. A 107 (2003) 9251
92. For reviews on cooperativity see
93. Williams D.H., Stephens E., O'Brien D.P., and Zhou M. Angew. Chem. Int. Ed. 43 (2004) 6596
94. Hunter C.A., and Tomas S. Chem. Biol. 10 (2003) 1023
95. Ercolani G. J. Am. Chem. Soc. 125 (2003) 16097
96. Tobey S.L., and Anslyn E.V. J. Am. Chem. Soc. 125 (2003) 10963
97. Schlund S., Schmuck C., and Engels B. J. Am. Chem. Soc. 127 (2005) 11115
98. For selected examples on the complexation of amino acids in aqueous solvents see
99. Escuder B., Rowan A.E., Feiters M.C., and Nolte R.J.M. Tetrahedron 60 (2004) 291
100. Hernández J.V., Muñiz F.M., Oliva A.I., Simón L., Pérez E., and Morán J.R. Tetrahedron Lett. 44 (2003) 6983
101. Arena G., Contino A., Gulino F.G., Magrì A., Sansone F., Sciotto D., and Ungaro R. Tetrahedron Lett. 40 (2003) 1597
102. Higashi N., Koga T., and Niwa M. Chembiochem 3 (2002) 448
103. Grawe T., Schrader T., Finocchiaro P., Consiglio G., and Failla S. Org. Lett. 3 (2001) 1597
104. Ait-Haddou H., Wiskur S.L., Lynch V.M., and Anslyn E.V. J. Am. Chem. Soc. 123 (2001) 11296
105. Mizutani T., Wada K., and Kitagawa S. J. Am. Chem. Soc. 121 (1999) 11425
106. Ma J.C., and Dougherty D.A. Chem. Rev. 97 (1997) 1303
107. Dougherty D.A. Science 271 (1996) 163
108. Schmuck C., and Geiger L. J. Am. Chem. Soc. 127 (2005) 10486
109. Some recent examples of metal-based peptide binding
110. Buryak A., and Severin K. Angew. Chem. Int. Ed. 43 (2004) 4771
111. Imai H., Munakata H., Uemori Y., and Sakura N. Inorg. Chem. 43 (2004) 1211
112. Wright A.T., and Anslyn E.V. Org. Lett. 6 (2004) 1341
113. Sirish M., Chertkov V., and Schneider H.-J. Chem. Eur. J. 8 (2002) 1181
114. Ogoshi H., and Mizutani T. Acc. Chem. Res. 31 (1998) 81
115. Süssmuth R.D. Chembiochem 3 (2002) 295
116. Nicolaou K.C., Boddy C.N.C., Bräse S., and Wissinger N. Angew. Chem. Int. Ed. Engl. 38 (1999) 2096
117. Williams D.H., and Bardesley B. Angew. Chem. Int. Ed. Engl. 38 (1999) 1172
118. Walsh C. Science 284 (1999) 442
119. Wittinghofer A., and Waldmann H. Angew. Chem. Int. Ed. Engl. 39 (2000) 4192
120. Hinterding K., Alonso-Díaz D., and Waldmann H. Angew. Chem. Int. Ed. Engl. 37 (1998) 688
121. Reviews on chemosensors
122. Martinez-Manez R., and Sancenon F. Chem. Rev. 103 (2003) 4419
123. Czarnik A.W., and Yoon J. Perspect. Supramol. Chem. 4 (1999) 177
124. De Silva A.P., Gunaratne H.Q.N., Gunnlaugsson T., Huxley A.J.M., McCoy C.P., Rademacher J.T., and Rice T.E. Chem. Rev. 97 (1997) 1515
125. Czarnik A.W. Chem. Biol. 2 (1995) 423
126. For two recent examples see
127. Salvatella X., Martinell M., Gairí M., Mateu M.G., Feliz M., Hamilton A.D., de Mendoza J., and Giralt E. Angew. Chem. Int. Ed. 43 (2004) 196
128. Breccia P., vanGool M., Peréz-Fernandez R., Martín-Santamaria S., Gago F., Prados P., and de Mendoza J. J. Am. Chem. Soc. 125 (2003) 8270
129. For a review see:. Peczuh M.W., and Hamilton A.D. Chem. Rev. 100 (2000) 2479
130. For review articles on artificial peptide receptors see
131. Peczuh M.W., and Hamilton A.D. Chem. Rev. 100 (2000) 2479
132. Schneider H.-J. Adv. Supramol. Chem. 6 (2000) 185
133. Schneider H.-J. Angew. Chem. Int. Ed. Engl. 32 (1993) 848
134. Webb T.H., and Wilcox C.S. Chem. Soc. Rev. 22 (1993) 383
135. Van Regenmortel M.H.V. J. Mol. Recognit. 13 (2000) 1
136. For review articles on the use of combinatorial receptor libraries see
137. Srinivasan N., and Kilburn J.D. Curr. Opin. Chem. Biol. 8 (2004) 305
138. Linton B., and Hamilton A.D. Curr. Opin. Chem. Biol. 3 (1999) 307
139. DeMiguel Y.R., and Sanders J.M.K. Curr. Opin. Chem. Biol. 2 (1998) 417
140. Still W.C. Acc. Chem. Res. 29 (1996) 155
141. Schmuck C., and Geiger L. J. Am. Chem. Soc. 126 (2004) 8898
142. Nowick J.S., and Insaf S. J. Am. Chem. Soc. 119 (1997) 10903
143. Jensen K., Braxmeier T.M., Demarcus M., Frey J.G., and Kilburn J.D. Chem. Eur. J. 8 (2002) 1300
144. Xuo R., Greiveldinger G., Marenus L.E., Cooper A., and Ellman J.A. J. Am. Chem. Soc. 121 (1999) 4898
145. Wennemers H., Nold M.C., Conza M.M., Kulicke K.J., and Neuburger M. Chem. Eur. J. 9 (2003) 442
146. Conza M., and Wennemers H. J. Org. Chem. 67 (2002) 2696
147. Wennemers H., Conza M., Nold M., and Krattiger P. Chem. Eur. J. 7 (2001) 3342
148. Kuruvilla F.G., Shamji A.F., Sternson S.M., Hergenrother P.J., and Schreiber S.L. Nature 416 (2002) 652
149. Breinbauer R., Vetter I.R., and Waldmann H. Angew. Chem. Int. Ed. 41 (2002) 2878
150. Schmuck C., and Heil M. Chembiochem 4 (2003) 1232
151. Schmuck C., and Heil M. Org. Biomol. Chem. 1 (2003) 633
152. Zerovnik E. Eur. J. Biochem. 269 (2002) 3362
153. Hardy J., and Selkoe D.J. Science 297 (2002) 353
154. Austen B., and Manca M. Chem. Br. (2000) 28
155. Gopinath L. Chem. Br. (1998) 38
156. Lansbury Jr. P.T. Acc. Chem. Res. 29 (1996) 317
157. Yankner B.A. Neuron 16 (1996) 921
158. Jarret J.T., Berger E.P., and Lansbury Jr. P.T. Biochemistry 32 (1993) 4693
159. Kuroda Y., Maeda K., Hanaoka H., Miyamoto K., and Nakagawa T. J. Pept. Sci. 10 (2004) 8
160. Rzepecki P., Gallmeier H., Geib N., Cernovska K., König B., and Schrader T. J. Org. Chem. 69 (2004) 5168
161. Hetényi C., Szabo Z., Klement E., Datki Z., Körtvélyesi T., Zarandi M., and Penke B. Biochem. Biophys. Res. Commun. 292 (2002) 931
162. Hetényi C., Körtvélyesi T., and Penke B. Bioorg. Med. Chem. 10 (2002) 1587
163. Lowe T.L., Strzelec A., Kiessling L.L., and Murphy R.M. Biochemistry 40 (2001) 7882
164. Hetényi C., Körtvélyesi T., and Penke B. J. Mol. Struct. (Theochem) 542 (2001) 25
165. Tjernberg L.O., Callaway D.J.E., Tjernberg A., Hahne S., Lilliehöök C., Terenius L., Thyberg J., and Nordstedt C. J. Biol. Chem. 274 (1999) 12619
166. Soto C. Mol. Med. Today 5 (1999) 343
167. Soto C., Kindy M.S., Baumann M., and Frangione B. Biochem. Biophys. Res. Commun. 226 (1996) 672
168. Ghanta J., Shen C.-L., Kiessling L.L., and Murphy R.M. J. Biol. Chem. 271 (1996) 29525
169. Lam K.S., Lebl M., and Krchnak V. Chem. Rev. 97 (1997) 411
170. Yoon S.S., and Still W.C. Tetrahedron 51 (1995) 567
171. Lansbury Jr. P.T., Costa P.R., Griffiths J.M., Simon E.J., Auger M., Halverson K.J., Kocisko D.A., Hendsch Z.S., Ashbury T.T., Spencer R.G.S., Tidor B., and Griffin R.G. Nat. Struct. Biol. 2 (1995) 990
172. Schmuck C., Frey P., and Heil M. Chembiochem 6 (2005) 628
173. Schmuck C., Heil M., Scheiber J., and Baumann K. Angew. Chem. Int. Ed. 44 (2005) 7208
174. Schmuck C., and Heil M. Chem. Eur. J. 12 (2006) 1339