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For review articles on artificial peptide receptors see: a) M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2494;
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c) K. Jensen, T. M. Braxmeier, M. Demarcus, J. G. Frey, J. D. Kilburn, Chem. Eur. J. 2002, 8, 1300-1309;
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Jensen, K.1
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d) R. Xuo, G. Greiveldinger, L. E. Marenus, A. Cooper, J. A. Ellman, J. Am. Chem. Soc. 1999, 121, 4898-4899;
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Xuo, R.1
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f) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537;
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Breslow, R.1
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Odobel, F.5
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g) M. W. Peczuh, A. D. Hamilton, J. Sanchez-Qesada, J. de Mendoza, T. Haak, E. Giralt, J. Am. Chem. Soc. 1997, 119, 9327-9328;
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Peczuh, M.W.1
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De Mendoza, J.4
Haak, T.5
Giralt, E.6
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16
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0032978519
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The importance of the interplay between hydrophobic interactions and H-bonds ("hydrophobic cluster formation") has been demonstrated, for example, by Kelly in his work on β-sheet nucleators: a) P. Chitnumsub, W. R. Fiori, H. A. Lashuel, H. Diaz, J. W. Kelly, Bioorg. Med. Chem. 1999, 7, 39-59;
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Chitnumsub, P.1
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b) K. Y. Tsang, H. Diaz, N. Graciana, J. W. Kelly, J. Am. Chem. Soc. 1994, 116, 3988-4005;
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Tsang, K.Y.1
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d) B. A. Yankner, Neuron 1996, 16, 921-932.
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Yankner, B.A.1
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J. T. Jarret, E. P. Berger, P. T. Lansbury, Jr., Biochemistry 1993, 32, 4693-4697.
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Biochemistry
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Jarret, J.T.1
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0000485604
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a) J. J. Lavigne, E. V. Anslyn, Angew. Chem. 2001, 113, 3212-3225; Angew. Chem. Int. Ed. 2001, 40, 3118-3130;
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Angew. Chem.
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Lavigne, J.J.1
Anslyn, E.V.2
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0035801512
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a) J. J. Lavigne, E. V. Anslyn, Angew. Chem. 2001, 113, 3212-3225; Angew. Chem. Int. Ed. 2001, 40, 3118-3130;
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Angew. Chem. Int. Ed.
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, pp. 3118-3130
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32
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0036009284
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Review articles on the binding of carboxylates by artificial hosts including guanidinium-based systems: a) R. J. Fitzmaurice, G. M. Kyne, D. Douheret, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2002, 841-864;
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J. Chem. Soc. Perkin Trans. 1
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Fitzmaurice, R.J.1
Kyne, G.M.2
Douheret, D.3
Kilburn, J.D.4
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34
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0001770672
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Artificial Anion Hosts: Concepts for Structure and Guest Binding
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F. P. Schmidtchen, (Eds.: A. Bianchi, K. Bowman-James, E. García-España), Wiley-VCH, Weinheim
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c) "Artificial Anion Hosts: Concepts for Structure and Guest Binding" F. P. Schmidtchen in Supramolecular Chemistry of Anions (Eds.: A. Bianchi, K. Bowman-James, E. García-España), Wiley-VCH, Weinheim, 1997, pp. 79-146;
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(1997)
Supramolecular Chemistry of Anions
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35
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0000571928
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Structural and Topological Aspects of Anion Coordination
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J. L. Atwood, J. W. Steed, (Eds.: A. Bianchi, K. Bowman-James, E. García-España), Wiley-VCH: New York
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d) "Structural and Topological Aspects of Anion Coordination" J. L. Atwood, J. W. Steed in Supramolecular Chemistry of Anions (Eds.: A. Bianchi, K. Bowman-James, E. García-España), Wiley-VCH: New York, 1997, pp. 147-216.
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(1997)
Supramolecular Chemistry of Anions
, pp. 147-216
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36
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0042508739
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We were recently able to show that one-armed cationic receptors of this general type attached to a solid support are capable of binding an anionic tetrapeptide, at least in organic solvents (DMSO, methanol): C. Schmuck, M. Heil, Org. Biomol. Chem. 2003, 1, 633-636.
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Org. Biomol. Chem.
, vol.1
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Schmuck, C.1
Heil, M.2
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K. S. Lam, M. Lebl, V. Krchnak, Chem. Rev. 1997, 97, 411-448.
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Chem. Rev.
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Lam, K.S.1
Lebl, M.2
Krchnak, V.3
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39
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85007630016
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-
note
-
The successful synthesis of the receptors on the solid support was monitored for selected examples by solid-state MAS-NMR and ESI-MS experiments and their respective cleavage from the solid support and subsequent isolation; see also Experimental Section.
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40
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0008003449
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a) P.W. Smith, G. Chang, W.C. Still, J. Org. Chem. 1988, 53, 1587-1590
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J. Org. Chem.
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Smith, P.W.1
Chang, G.2
Still, W.C.3
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0029925955
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c) Y. Cheng, T. Suenaga, W. C. Still, J. Am. Chem. Soc. 1996, 118, 1813-1814;
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Cheng, Y.1
Suenaga, T.2
Still, W.C.3
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44
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85007650545
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-
note
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ass for each receptor was calculated.
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45
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0028804827
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-
P. T. Lansbury, Jr., P. R. Costa, J. M. Griffiths, E. J. Simon, M. Auger, K. J. Halverson, K. J. Kocisko, Z. S. Hendsch, T. T. Ashbury, R. G. S. Spencer, B. Tidor, R. G. Griffin, Nat. Struct. Biol. 1995, 2, 990-998.
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Lansbury, P.T.1
Costa, P.R.2
Griffiths, J.M.3
Simon, E.J.4
Auger, M.5
Halverson, K.J.6
Kocisko, K.J.7
Hendsch, Z.S.8
Ashbury, T.T.9
Spencer, R.G.S.10
Tidor, B.11
Griffin, R.G.12
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47
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85007639431
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note
-
For a typical UV titration, aliquots of the substrate 10 (0.58 mM) were added to a solution of the receptor (0.0546 mM) in bis-tris buffer (0.78 mM, pH 6.1). The UV spectra were recorded after each addition. Analysis of the data was performed with the Specfit/32 software program from Spectrum Software Associates.
-
-
-
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48
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85007639296
-
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note
-
-1), did not give any reasonable data. The binding constant was too low to be measured accurately in free solution by UV titration, which is again in good agreement with the rather poor binding affinity of this specific receptor observed in the on-bead assay.
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50
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84986437005
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F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440-467.
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(1990)
J. Comput. Chem.
, vol.11
, pp. 440-467
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-
Mohamadi, F.1
Richards, N.G.J.2
Guida, W.C.3
Liskamp, R.4
Lipton, M.5
Caufield, C.6
Chang, G.7
Hendrickson, T.8
Still, W.C.9
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51
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85007654065
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note
-
Because of the limited solubilities both of the free peptide and of the receptors at concentrations > 10mM in aqueous solvents, the NMR studies had to be performed in DMSO. Although the relative importance of H-bonds/ ion-pairing versus hydrophobic interactions should be shifted towards the hydrophobic interactions in water, the observation of the H-bonded pattern required for a β sheet in DMSO is also a necessary prerequisite for its occurrence in water.
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