-
1
-
-
0033549475
-
-
Recent examples of synthetic receptors for peptides, see: (a) T. Fessmann and J. D. Kilburn, Angew. Chem., Int. Ed., 1999, 38, 1993;
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 1993
-
-
Fessmann, T.1
Kilburn, J.D.2
-
2
-
-
0033606246
-
-
(b) R. Xu, G. Greiveldinger, L. E. Marenus, A. Cooper and J. A. Ellman, J. Am. Chem. Soc., 1999, 121, 4898;
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 4898
-
-
Xu, R.1
Greiveldinger, G.2
Marenus, L.E.3
Cooper, A.4
Ellman, J.A.5
-
4
-
-
0032925548
-
-
J. Dowden, P. D. Edwards, S. S. Flack and J. D. Kilburn, Chem. Eur J., 1999, 5, 79;
-
(1999)
Chem. Eur J.
, vol.5
, pp. 79
-
-
Dowden, J.1
Edwards, P.D.2
Flack, S.S.3
Kilburn, J.D.4
-
6
-
-
0000709062
-
-
(f) R. Breslow, Z. Yang, R. Ching, G. Trojandt and F. Odobel, J. Am. Ghent. Soc., 1998, 120, 3536;
-
(1998)
J. Am. Ghent. Soc.
, vol.120
, pp. 3536
-
-
Breslow, R.1
Yang, Z.2
Ching, R.3
Trojandt, G.4
Odobel, F.5
-
7
-
-
0039302822
-
-
(g) D. W. P. M.Löwik, M. D. Weingarten, M. Broekema, A. J. Brouwer, W. C. Still and R. M. J. Liskamp, Angew. Chent., Int. Ed., 1998, 37, 1846;
-
(1998)
Angew. Chent., Int. Ed.
, vol.37
, pp. 1846
-
-
M.löwik, D.W.P.1
Weingarten, M.D.2
Broekema, M.3
Brouwer, A.J.4
Still, W.C.5
Liskamp, R.M.J.6
-
8
-
-
0031764606
-
-
(h) M. Davies, M. Bonnat, F. Guillier, J. D. Kilburn and M. Bradley, J. Org. Chem., 1998, 63, 8696;
-
(1998)
J. Org. Chem.
, vol.63
, pp. 8696
-
-
Davies, M.1
Bonnat, M.2
Guillier, F.3
Kilburn, J.D.4
Bradley, M.5
-
9
-
-
0347802782
-
-
R. J. Pieters, J. Cuntze, M. Bonnet and F. Diederich, J. Chem. Soc., Perkin Trans. 2, 1997, 1891;
-
(1997)
J. Chem. Soc., Perkin Trans. 2
, vol.1891
-
-
Pieters, R.J.1
Cuntze, J.2
Bonnet, M.3
Diederich, F.4
-
11
-
-
0031562063
-
-
See reference 1 (d) and (a) J. Dowden, P. D. Edwards and J. D. Kilburn, Tetrahedron Lett., 1997, 38, 1095;
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 1095
-
-
Dowden, J.1
Edwards, P.D.2
Kilburn, J.D.3
-
13
-
-
0029955112
-
-
(a) G. J. Pernia, J. D. Kilburn, J. W. Essex, R. J. Mortishire-Smith and M. Rowley, J. Am. Chem. Soc., 1996, 118, 10220;
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 10220
-
-
Pernia, G.J.1
Kilburn, J.D.2
Essex, J.W.3
Mortishire-Smith, R.J.4
Rowley, M.5
-
14
-
-
37049083581
-
-
(b) G. J. Pernia, J. D. Kilburn and M. Rowley, J. Chem. Soc., Chem. Commun., 1995, 305.
-
(1995)
J. Chem. Soc., Chem. Commun.
, pp. 305
-
-
Pernia, G.J.1
Kilburn, J.D.2
Rowley, M.3
-
15
-
-
0028968852
-
-
For a preliminary communication of a part of this work, see: C. P. Waymark, J. D. Kilburn and I. Gillies, Tetrahedron Lett., 1995, 36, 3051.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 3051
-
-
Waymark, C.P.1
Kilburn, J.D.2
Gillies, I.3
-
16
-
-
0028923735
-
-
(a) R. S. Wareham, J. D. Kilburn, N. H. Rees, D. L. Turner, A. R. Leach and D. S. Holmes, Tetrahedron Lett., 1995, 36, 3047;
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 3047
-
-
Wareham, R.S.1
Kilburn, J.D.2
Rees, N.H.3
Turner, D.L.4
Leach, A.R.5
Holmes, D.S.6
-
17
-
-
33751135463
-
-
(b) R. S. Wareham, J. D. Kilburn, N. H. Rees, D. L. Turner and D. S. Holmes, Angew. Chem., Int. Ed. Engl., 1995, 34, 2660.
-
(1995)
Angew. Chem., Int. Ed. Engl.
, vol.34
, pp. 2660
-
-
Wareham, R.S.1
Kilburn, J.D.2
Rees, N.H.3
Turner, D.L.4
Holmes, D.S.5
-
18
-
-
0001201464
-
-
Although the dicyclohexylcarbodiimide coupling proved the method of choice in this instance, we have had difficulties coupling other amino acids with diaminopyridine and have found that the most reliable method involves preactivation of the diaminopyridine with bis(trimethylsilyl)acetamide (S. Rajeswari, R. J. Jones and M. P. Cava, Tetrahedron Lett., 1987, 28, 5099) and coupling with the acid fluoride derived from the amino acid by treatment with cyanuric fluoride
-
(1987)
Tetrahedron Lett.
, vol.28
, pp. 5099
-
-
Rajeswari, S.1
Jones, R.J.2
Cava, M.P.3
-
19
-
-
0025671995
-
-
(L. A. Carpino, D. Sadat-Aalaee, H. G. Chao and R. H. DeSeims, J. Am. Chem. Soc., 1990, 112, 9651) .
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 9651
-
-
Carpino, L.A.1
Sadat-Aalaee, D.2
Chao, H.G.3
DeSeims, R.H.4
-
20
-
-
85004829973
-
-
H. Kunz, H. Waldmann and C. Unverzagt, Int. J. Pept. Protein Res., 1985, 26, 493.
-
(1985)
Int. J. Pept. Protein Res.
, vol.26
, pp. 493
-
-
Kunz, H.1
Waldmann, H.2
Unverzagt, C.3
-
28
-
-
33645950870
-
-
University of Pittsburgh, USA, © C. S. Wilcox and the University of Pittsburgh
-
Hostest 5 software: C. S. Wilcox and N. M. Glagovich, University of Pittsburgh, USA, © C. S. Wilcox and the University of Pittsburgh, 1993. See also
-
(1993)
-
-
Wilcox, C.S.1
Glagovich, N.M.2
-
29
-
-
33645922235
-
-
ed. H.-J. Schneider and H. Durr, VCH, Weinheim
-
(a) C. S. Wilcox, Design, Synthesis and Evaluation of an Efficacious Functional Group Dyad. Methods and Limitations in the Use of NMR for Measuring Host-Guest Interactions, in Frontiers in Supramotccular Organic Chemistry and Photochemistry, ed. H.-J. Schneider and H. Durr, VCH, Weinheim, 1991;
-
(1991)
Design, Synthesis and Evaluation of An Efficacious Functional Group Dyad. Methods and Limitations in the Use of NMR for Measuring Host-Guest Interactions, in Frontiers in Supramotccular Organic Chemistry and Photochemistry
-
-
Wilcox, C.S.1
-
30
-
-
0343885449
-
-
(b) C. S. Wilcox, J. C. Adrian, Jr., T. H. Webb and F. J. Zawacki, J. Am. Chem. Soc., 1992, 114, 10189.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 10189
-
-
Wilcox, C.S.1
Adrian Jr., J.C.2
Webb, T.H.3
Zawacki, F.J.4
-
31
-
-
33645898730
-
-
note
-
2 symmetry, so that while a hydrogen bond is only formed with one of two symmetrically related protons, the NMR reports the time-averaged signal for the hydrogen-bonded and non-hydrogen bonded partner.
-
-
-
-
32
-
-
33645956635
-
-
note
-
In the case of the titration experiment with what turned out to be the most tightly bound substrate, Cbz-β-alanyl-D-alanine, we did monitor the shift of the phenylalanyl α-proton (Δδ = 0.4) and the aromatic rim proton ortho to the carboxamide (Δδ= -0.12). Analysis of the resulting data gave association constants in agreement with those determined from monitoring the amidopyridine NH, but the quality of the fit for the data from the phenylalanyl α-proton and aromatic rim proton was not as good, due to loss of resolution and the presence of overlapping signals from both host and guest protons as the titration progressed.
-
-
-
-
33
-
-
12044255753
-
-
Comparison of binding constants of structurally different carboxylic acids should be treated with some caution since the strength of the interaction with the amidopyridine unit will be influenced by the acidity of the carboxylic acid moiety (see e.g., M. H. Abraham, Chem. Soc. Rcr., 1993, 22, 73;
-
(1993)
Chem. Soc. Rcr.
, vol.22
, pp. 73
-
-
Abraham, M.H.1
-
34
-
-
0029926948
-
-
see also S. Shan, S. Loh and D. Herschlag, Science, 1996, 272, 97).
-
(1996)
Science
, vol.272
, pp. 97
-
-
Shan, S.1
Loh, S.2
Herschlag, D.3
-
35
-
-
33645941009
-
-
note
-
Thus, for example, the difference in binding strength of hexanoic and phenylacetic acid may be partly due to the difference in their acidities. However, the differences in acidities, in chloroform solution, of closely related amino acid substrates are likely to be small and are unlikely to lead to differences in the interaction with the amidopyridine unit which exceed the error in the experimentally determined binding constants and clearly for enantiomers of the same substrate the acidities will be the same.
-
-
-
-
36
-
-
0029678259
-
-
(a) C. T. Walsh, S. L. Fisher, I.-S. Park, M. Prahalad and Z. Wu, Chem. Biol., 1996, 3, 21;
-
(1996)
Chem. Biol.
, vol.3
, pp. 21
-
-
Walsh, C.T.1
Fisher, S.L.2
Park, I.-S.3
Prahalad, M.4
Wu, Z.5
-
37
-
-
0030036053
-
-
(b) R. J. Dancer, A. C. Try, G. J. Sharman and D. H. Williams, Chem. Commun., 1996, 1445.
-
(1996)
Chem. Commun.
, pp. 1445
-
-
Dancer, R.J.1
Try, A.C.2
Sharman, G.J.3
Williams, D.H.4
-
39
-
-
84986437005
-
-
F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson and W. C. Still, J. Comput. Chem., 1990, 11, 440.
-
(1990)
J. Comput. Chem.
, vol.11
, pp. 440
-
-
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
-
41
-
-
0029011701
-
-
(a) W. D. Cornell, P. Ceiplak, C. I. Baoyly, I. R. Gould, K. M. Merz, Jr., D. M. Ferguson, D. C. Spellmeyer, T. Fox, J. W. Caldwell and P. A. Kollman, J. Am. Chem. Soc., 1995, 117, 5179;
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 5179
-
-
Cornell, W.D.1
Ceiplak, P.2
Baoyly, C.I.3
Gould, I.R.4
Merz Jr., K.M.5
Ferguson, D.M.6
Spellmeyer, D.C.7
Fox, T.8
Caldwell, J.W.9
Kollman, P.A.10
-
42
-
-
0021757436
-
-
(b) S. J. Weiner, P. A. Kollman, D. A. Case, U. C. Singh, C. Chio, G. Alagona, S. Profeta, Jr. and P. Weiner, J. Am. Chem. Soc., 1984, 106, 765;
-
(1984)
J. Am. Chem. Soc.
, vol.106
, pp. 765
-
-
Weiner, S.J.1
Kollman, P.A.2
Case, D.A.3
Singh, U.C.4
Chio, C.5
Alagona, G.6
Profeta Jr., S.7
Weiner, P.8
-
43
-
-
84988053694
-
-
(c) S. J. Weiner, P. A. Kollman and D. A. Case, J. Comput. Chem., 1986, 7, 230.
-
(1986)
J. Comput. Chem.
, vol.7
, pp. 230
-
-
Weiner, S.J.1
Kollman, P.A.2
Case, D.A.3
-
44
-
-
0344778061
-
-
W. C. Still, A. Tempczyk and R. C. Hawley, J. Am. Chem. Soc., 1990, 112, 6127.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 6127
-
-
Still, W.C.1
Tempczyk, A.2
Hawley, R.C.3
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