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1
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20844461981
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note
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Typical examples are cycloadditions or cyclization reactions and intramolecular folding.
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2
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0031576660
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One important motivation to develop synthetic binding sites for peptide β-sheets is the interception of prion protein aggregation. (a) Kirsten, C. N.; Schrader, T. H. J. Am. Chem. Soc. 1997, 119, 12061-12068.
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(b) Wehner, M.; Schrader, T. Angew. Chem., Int. Ed. 2002, 41, 1751-1754.
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Wehner, M.1
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Cernovska, K.; Kemter, M.; Gallmeier, H.-C.; Rzepecki, P.; Schrader, T. H.; König, B. Org. Biomol. Chem. 2004, 2, 1603-1611.
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Cernovska, K.1
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(a) Nowick, J. S.; Chung, D. M. Angew. Chem., Int. Ed. 2003, 42, 1765-1768.
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7
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Nowick, J. S.; Lam, S. K.; Khasanova, T. V.; Kemnitzer, W. E.; Maitra, S.; Mee, H. T.; Liu, R. J. Am. Chem. Soc. 2002, 124, 4972-4973.
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Mee, H.T.6
Liu, R.7
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9
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(a) Woll, M. G.; Lai, J. R.; Guzei, I. A.; Taylor, S. J. C.; Smith, M. E. B.; Gellman, S. H. J. Am. Chem. Soc. 2001, 123, 11077-11078.
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Bonauer, C.1
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13
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20844449479
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note
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Many examples of intermolecular β-sheet binders based on complementary hydrogen bonding patterns have been reported, but their use is mostly restricted to nonpolar solvents, which do not intercept the hydrogen bonds.
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15
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0030783018
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Such ionic interactions provide much higher affinity than hydrogen bonds and allow peptide binding in polar solvents. Examples of carboxyl group binding: (a) Peczuh, M. W.; Hamilton, A. D.; Sánchez-Quesada, J.; de Mendoza, J.; Haack, T.; Giralt, E. J. Am. Chem. Soc. 1997, 119, 9327-9328. Example of phosphate-binding:
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Peczuh, M.W.1
Hamilton, A.D.2
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Haack, T.5
Giralt, E.6
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1542366681
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(b) Ojida, A.; Mito-oka, Y.; Sada, K.; Hamachi, I. J. Am. Chem. Soc. 2004, 126, 2454-2463. Examples of ammonium group binding:
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Ojida, A.1
Mito-oka, Y.2
Sada, K.3
Hamachi, I.4
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18
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0037087665
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Herm, M.; Molt, O.; Schrader, T. H. Chem. Eur. J. 2002, 8, 1485-1499. Examples of binding to hydrophobic groups or areas:
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Chem. Eur. J.
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Herm, M.1
Molt, O.2
Schrader, T.H.3
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0000709062
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(e) Breslow, R.; Yang, Z.; Ching, R.; Trojandt, G.; Odobel, F. J. Am. Chem. Soc. 1998, 120, 3536-3537.
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20
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2442567699
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(f) Baldini, L.; Wilson, A. J.; Hong, J.; Hamilton, A. D. J. Am. Chem. Soc. 2004, 126, 5656-5657.
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Baldini, L.1
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Hamilton, A.D.4
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22
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(h) Ernst, J. T.; Kutzki, O.; Debnath, A. K.; Jiang, S.; Lu, H.; Hamilton, A. D. Angew. Chem., Int. Ed. 2002, 41, 117-119.
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Ernst, J.T.1
Kutzki, O.2
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Lu, H.5
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23
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0037091002
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Jasper, C.; Schrader, T.; Panitzky, J.; Klärner, F.-G. Angew. Chem., Int. Ed. 2002, 41, 1355-1358.
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Jasper, C.1
Schrader, T.2
Panitzky, J.3
Klärner, F.-G.4
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24
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(j) Malinovski, V.; Tumir, L.; Piantanida, I.; Zinic, M.; Schneider, H.-J. Eur. J. Org. Chem. 2002, 3785-3795.
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Malinovski, V.1
Tumir, L.2
Piantanida, I.3
Zinic, M.4
Schneider, H.-J.5
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26
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2442564646
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Other examples of combined use of different reversible interaction: Ligand to metal coordination and ionic interaction: (a) Wright, A. T.; Anslyn, E. V. Org. Lett. 2004, 6, 1341-1344. Ligand to metal coordination and hydrogen bonding:
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Org. Lett.
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Wright, A.T.1
Anslyn, E.V.2
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28
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4243140363
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Wiskur, S. L.; Lavigne, J. J.; Metzger, A.; Tobey, S. L.; Lynch, V.; Anslyn, E. V. Chem. Eur. J. 2004, 10, 3792-3804.
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Metzger, A.3
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(e) Shirin, Z.; Hammes, B. S.; Young, V. G.; Borovik, A. S. J. Am. Chem. Soc. 2000, 122, 1836-1837.
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0035959021
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(f) MacBeth, E. C.; Hammes, B. S.; Young, V. G.; Borovik, A. S. Inorg. Chem. 2001, 40, 4733-4741.
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32
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0011217383
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(a) Beauchamp, A. L.; Israeli, J.; Saulnier, H. Can. J. Chem. 1969, 47, 1269-1273.
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Beauchamp, A.L.1
Israeli, J.2
Saulnier, H.3
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35
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20844448129
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note
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3L/mol with our apparatus.
-
-
-
-
36
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20844451977
-
-
note
-
Methyl ester was used to avoid any additional ionic interactions of the carboxylate group.
-
-
-
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37
-
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20844444405
-
-
note
-
This concept of using intramolecular hydrogen bonds to planarize a β-sheet mimic was extensively used by Nowick in methoxy-substituted hydrazine benzoic acids.
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-
-
-
38
-
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20844458014
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note
-
Overlap of resonance signals restricts the number of detectable cross-peaks.
-
-
-
-
39
-
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20844457230
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-
note
-
NHHα coupling constants of the nonbound pentapeptide are given in Supporting Information.
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-
-
-
40
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20844461752
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Importance of comparing modeling results with primary derived data was recently described. Glättli, A.; van Gunsteren, W. F. Angew. Chem. 2004, 116, 6472-6476.
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Glättli, A.1
Van Gunsteren, W.F.2
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41
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20844437850
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note
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Absence of intermolecular contacts shows that no aggregates are formed between peptides or peptide and MOPAS under the experimental conditions.
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-
-
-
42
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4444278825
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(a) Banerjee, A. L.; Swanson, M.; Roy, B. C.; Jia, X.; Haldar, M. K.; Mallik, S.; Srivastava, D. K. J. Am. Chem. Soc. 2004, 126, 10875-10883.
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Banerjee, A.L.1
Swanson, M.2
Roy, B.C.3
Jia, X.4
Haldar, M.K.5
Mallik, S.6
Srivastava, D.K.7
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43
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6044239456
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(b) Roy, B. C.; Banerjee, A. L.; Swanson, M.; Jia, X. G.; Haldar, M. K.; Mallik, S.; Srivastava, D. K. J. Am. Chem. Soc. 2004, 126, 13206-13207.
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Roy, B.C.1
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Haldar, M.K.5
Mallik, S.6
Srivastava, D.K.7
-
44
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20844445535
-
-
note
-
Affinity was determined by microcalorimetry. Paramagnetism of the copper complex and substantial line broadening in the nickel complex so far have prevented a detailed investigation of the structure-inducing effect of the receptor on the pentapeptide in water.
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45
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1942467041
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Ojida, A.; Miyahara, Y.; Kohira, T.; Hamachi, I. Biopolymers 2004, 76, 177.
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Ojida, A.1
Miyahara, Y.2
Kohira, T.3
Hamachi, I.4
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