-
1
-
-
84891014181
-
-
For reviews, see: a, Eds, T. Schrader, A. D. Hamilton, Wiley-VCH, Weinheim, Germany
-
For reviews, see: a) A. P. Davis, T. D. James, in Functional Synthetic Receptors (Eds.: T. Schrader, A. D. Hamilton), Wiley-VCH, Weinheim, Germany, 2005, p. 45-109;
-
(2005)
Functional Synthetic Receptors
, pp. 45-109
-
-
Davis, A.P.1
James, T.D.2
-
3
-
-
53949105185
-
-
S. Penadés Ed, Springer-Verlag, Berlin
-
c) S. Penadés (Ed.), Host-Guest Chemistry - Mimetic Approaches to Study Carbohydrate Recognition, Top. Curr. Chem., vol. 218, Springer-Verlag, Berlin, 2002.
-
(2002)
Host-Guest Chemistry - Mimetic Approaches to Study Carbohydrate Recognition, Top. Curr. Chem
, vol.218
-
-
-
4
-
-
35548943201
-
-
For some recent examples of receptors operating through noncovalent interactions, see: a
-
For some recent examples of receptors operating through noncovalent interactions, see: a) Y. Ferrand, M. P. Crump, A. P. Davis, Science 2007, 318, 619-622;
-
(2007)
Science
, vol.318
, pp. 619-622
-
-
Ferrand, Y.1
Crump, M.P.2
Davis, A.P.3
-
5
-
-
34250007195
-
-
b) E. Klein, Y. Ferrand, E. K. Auty, A. P. Davis, Chem. Commun. 2007, 2390-2392;
-
(2007)
Chem. Commun
, pp. 2390-2392
-
-
Klein, E.1
Ferrand, Y.2
Auty, E.K.3
Davis, A.P.4
-
13
-
-
33644939001
-
-
j) M. Mazik, M. Kuschel, W. Sicking, Org. Lett. 2006, 8, 855-858;
-
(2006)
Org. Lett
, vol.8
, pp. 855-858
-
-
Mazik, M.1
Kuschel, M.2
Sicking, W.3
-
14
-
-
38149004121
-
-
k) O. Francesconi, A. Ienco, G. Moneti, C. Nativi, S. Roelens, Angew. Chem. 2006, 118, 6845-6848;
-
(2006)
Angew. Chem
, vol.118
, pp. 6845-6848
-
-
Francesconi, O.1
Ienco, A.2
Moneti, G.3
Nativi, C.4
Roelens, S.5
-
15
-
-
33750315369
-
-
l) M. Waki, H. Abe, M. Inouye, Chem. Eur. J. 2006, 12, 7839-7847;
-
(2006)
Chem. Eur. J
, vol.12
, pp. 7839-7847
-
-
Waki, M.1
Abe, H.2
Inouye, M.3
-
16
-
-
12344323898
-
-
m) H. Abe, Y. Aoyagi, M. Inouye, Org. Lett. 2005, 7, 59-61;
-
(2005)
Org. Lett
, vol.7
, pp. 59-61
-
-
Abe, H.1
Aoyagi, Y.2
Inouye, M.3
-
17
-
-
11844282808
-
-
n) E. Klein, M. P. Crump, A. P. Davis, Angew. Chem. Int. Ed. 2005, 44, 298-302;
-
(2005)
Angew. Chem. Int. Ed
, vol.44
, pp. 298-302
-
-
Klein, E.1
Crump, M.P.2
Davis, A.P.3
-
18
-
-
26844509098
-
-
o) M. G. J. Ten Cate, D. N. Reinhoudt, M. Crego-Calama, J. Org. Chem. 2005, 70, 8443-8453;
-
(2005)
J. Org. Chem
, vol.70
, pp. 8443-8453
-
-
Ten Cate, M.G.J.1
Reinhoudt, D.N.2
Crego-Calama, M.3
-
19
-
-
28044468193
-
-
p) H. Abe, N. Masuda, M. Waki, M. Inouye, J. Am. Chem. Soc. 2005, 127, 16189-16196;
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 16189-16196
-
-
Abe, H.1
Masuda, N.2
Waki, M.3
Inouye, M.4
-
20
-
-
21244463409
-
-
q) M. Mazik, H. Cavga, P. G. Jones, J. Am. Chem. Soc. 2005, 127, 9045-9052;
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 9045-9052
-
-
Mazik, M.1
Cavga, H.2
Jones, P.G.3
-
23
-
-
1642333937
-
-
t) T. Velasco, G. Lecollinet, T. Ryan, A. P. Davis, Org. Biol. Chem. 2004, 2, 645-647;
-
(2004)
Org. Biol. Chem
, vol.2
, pp. 645-647
-
-
Velasco, T.1
Lecollinet, G.2
Ryan, T.3
Davis, A.P.4
-
24
-
-
6344221022
-
-
u) J.-M. Fang, S. Selvi, J.-H. Liao, Z. Slanina, C.-T. Chen, P.-T. Chou, J. Am. Chem. Soc. 2004, 126, 645-647;
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 645-647
-
-
Fang, J.-M.1
Selvi, S.2
Liao, J.-H.3
Slanina, Z.4
Chen, C.-T.5
Chou, P.-T.6
-
25
-
-
0037260450
-
-
v) R. Welti, Y. Abel, V. Gramlich, F. Diederich, Helv. Chim. Acta 2003, 86, 548-562;
-
(2003)
Helv. Chim. Acta
, vol.86
, pp. 548-562
-
-
Welti, R.1
Abel, Y.2
Gramlich, V.3
Diederich, F.4
-
26
-
-
0038209638
-
-
w) K. Wada, T. Mizutani, S. Kitagawa, J. Org. Chem. 2003, 68, 5123-5131;
-
(2003)
J. Org. Chem
, vol.68
, pp. 5123-5131
-
-
Wada, K.1
Mizutani, T.2
Kitagawa, S.3
-
27
-
-
0042531917
-
-
x) M. Segura, B. Bricoli, A. Casnati, E. M. Muñoz, F. Sansone, R. Ungaro, C. Vicent, J. Org. Chem. 2003, 68, 6296-6303;
-
(2003)
J. Org. Chem
, vol.68
, pp. 6296-6303
-
-
Segura, M.1
Bricoli, B.2
Casnati, A.3
Muñoz, E.M.4
Sansone, F.5
Ungaro, R.6
Vicent, C.7
-
29
-
-
0142062931
-
-
z) M. Dukh, D. Šaman, K. Lang, V. Pouzar, I. Černy, P. Draŝar, V. Král, Org. Biomol. Chem. 2003, 1, 3458-3463.
-
(2003)
Org. Biomol. Chem
, vol.1
, pp. 3458-3463
-
-
Dukh, M.1
Šaman, D.2
Lang, K.3
Pouzar, V.4
Černy, I.5
Draŝar, P.6
Král, V.7
-
30
-
-
33749117446
-
-
Kluwer Academic Publishers, Dordrecht, The Netherlands
-
a) H. Lis, N. Sharon, Lectins, Kluwer Academic Publishers, Dordrecht, The Netherlands, 2003;
-
(2003)
Lectins
-
-
Lis, H.1
Sharon, N.2
-
35
-
-
0029008975
-
-
f) G. Hester, H. Kaku, I. J. Goldstein, C. S. Wright, Nat. Struct. Biol. 1995, 2, 472-479.
-
(1995)
Nat. Struct. Biol
, vol.2
, pp. 472-479
-
-
Hester, G.1
Kaku, H.2
Goldstein, I.J.3
Wright, C.S.4
-
36
-
-
6344253005
-
-
Our previous binding studies showed that 2-aminopyridines provide an excellent structural motif for binding carbohydrates, associated with the ability to form cooperative and bidentate hydrogen bonds with the sugar OH groups. See: a M. Mazik, W. Radunz, R. Boese, J. Org. Chem. 2004, 69, 7448-7462;
-
Our previous binding studies showed that 2-aminopyridines provide an excellent structural motif for binding carbohydrates, associated with the ability to form cooperative and bidentate hydrogen bonds with the sugar OH groups. See: a) M. Mazik, W. Radunz, R. Boese, J. Org. Chem. 2004, 69, 7448-7462;
-
-
-
-
38
-
-
0442264163
-
-
c) M. Mazik, W. Radunz, W. Sicking, Org. Lett. 2002, 4, 4579-4582;
-
(2002)
Org. Lett
, vol.4
, pp. 4579-4582
-
-
Mazik, M.1
Radunz, W.2
Sicking, W.3
-
40
-
-
0034603185
-
-
e) M. Mazik, H. Bandmann, W. Sicking, Angew. Chem. Int. Ed. 2000, 39, 551-554.
-
(2000)
Angew. Chem. Int. Ed
, vol.39
, pp. 551-554
-
-
Mazik, M.1
Bandmann, H.2
Sicking, W.3
-
41
-
-
0000970872
-
-
Anslyn and coworkers have exploited the 2-aminopyridine unit for binding of cyclohexanediols and -triols. See: C. Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778-2792.
-
Anslyn and coworkers have exploited the 2-aminopyridine unit for binding of cyclohexanediols and -triols. See: C. Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778-2792.
-
-
-
-
42
-
-
33947202577
-
-
The character of carbohydrate-aromatic interaction is still a subject of controversy; for recent discussions on the importance of carbohydrate-aromatic interactions, see: a G. Terraneo, D. Potenza, A. Canales, J. Jiménez-Barbero, K. K. Baldridge, A. Bernardi, J. Am. Chem. Soc. 2007, 129, 2890-2900;
-
The character of carbohydrate-aromatic interaction is still a subject of controversy; for recent discussions on the importance of carbohydrate-aromatic interactions, see: a) G. Terraneo, D. Potenza, A. Canales, J. Jiménez-Barbero, K. K. Baldridge, A. Bernardi, J. Am. Chem. Soc. 2007, 129, 2890-2900;
-
-
-
-
43
-
-
27944482492
-
-
b) M. I. Chávez, C. Andreu, P. Vidal, N. Aboitiz, F. Freire, P. Groves, J. L. Asensio, G. Asensio, M. Muraki, F. J. Caňada, J. Jiménez-Barbero, Chem. Eur. J. 2005, 11, 7060-7074.
-
(2005)
Chem. Eur. J
, vol.11
, pp. 7060-7074
-
-
Chávez, M.I.1
Andreu, C.2
Vidal, P.3
Aboitiz, N.4
Freire, F.5
Groves, P.6
Asensio, J.L.7
Asensio, G.8
Muraki, M.9
Caňada, F.J.10
Jiménez-Barbero, J.11
-
44
-
-
53949087968
-
-
For examples of CH-π interactions in the crystal structures of the complexes formed between artificial receptors and carbohydrates, see ref, 2q
-
[2q].
-
-
-
-
45
-
-
34250641915
-
-
Many biological interactions occur in enzyme pockets or in membranes, meaning that they occur in an environment with a lower dielectric constant than the bulk solvent. For this reason, many theoretical studies on different enzyme model systems have been performed in a medium with a lower dielectric constant (mostly ε = 5.7, corresponding to chlorobenzene). See, for example: a) K.-B. Cho, Y. Moreau, D. Kumar, D. A. Rock, J. P. Jones, S. Shaik, Chem. Eur. J. 2007, 13, 4103-4115;
-
Many biological interactions occur in enzyme pockets or in membranes, meaning that they occur in an environment with a lower dielectric constant than the bulk solvent. For this reason, many theoretical studies on different enzyme model systems have been performed in a medium with a lower dielectric constant (mostly ε = 5.7, corresponding to chlorobenzene). See, for example: a) K.-B. Cho, Y. Moreau, D. Kumar, D. A. Rock, J. P. Jones, S. Shaik, Chem. Eur. J. 2007, 13, 4103-4115;
-
-
-
-
46
-
-
0346365000
-
-
b) S. P. de Visser, S. Shaik, P. K. Sharma, D. Kumar, W. Thiel, J. Am. Chem. Soc. 2003, 125, 15779-15788;
-
(2003)
J. Am. Chem. Soc
, vol.125
, pp. 15779-15788
-
-
de Visser, S.P.1
Shaik, S.2
Sharma, P.K.3
Kumar, D.4
Thiel, W.5
-
48
-
-
0035932611
-
-
Recognition of neutral sugars in aqueous solution through noncovalent interactions remains an important challenge in artificial receptor chemistry; for some examples, see refs.[2a,2h,2n] and: a V. Král, O. Rusin, F. P. Schmidtchen, Org. Lett. 2001, 3, 873-876;
-
[2a,2h,2n] and: a) V. Král, O. Rusin, F. P. Schmidtchen, Org. Lett. 2001, 3, 873-876;
-
-
-
-
49
-
-
0034801352
-
-
b) R. D. Hubbard, S. R. Horner, B. L. Miller, J. Am. Chem. Soc. 2001, 123, 5810-5811;
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 5810-5811
-
-
Hubbard, R.D.1
Horner, S.R.2
Miller, B.L.3
-
51
-
-
0035766088
-
-
a) L. A. Cabell, M. D. Best, J. J. Lavigne, S. E. Schneider, D. M. Perreault, M.-K. Monahan, E. V. Anslyn, J. Chem. Soc. Perkin Trans. 2 2001, 315-323;
-
(2001)
J. Chem. Soc. Perkin Trans. 2
, pp. 315-323
-
-
Cabell, L.A.1
Best, M.D.2
Lavigne, J.J.3
Schneider, S.E.4
Perreault, D.M.5
Monahan, M.-K.6
Anslyn, E.V.7
-
52
-
-
23744500512
-
-
b) K. J. Wallace, R. Hanes, E. Anslyn, J. Morey, K. V. Kilway, J. Siegel, Synthesis 2005, 2080-2083.
-
(2005)
Synthesis
, pp. 2080-2083
-
-
Wallace, K.J.1
Hanes, R.2
Anslyn, E.3
Morey, J.4
Kilway, K.V.5
Siegel, J.6
-
53
-
-
53949090730
-
-
The binding constants were determined in chloroform at 25°C by titration experiments. Dilution experiments show that receptors do not self-aggregate in the concentration range used. For each system at least three 1H NMR titrations were carried out; for each titration 15-20 samples were prepared; b) Error in a single Ka estimation was less than 10, c K11 corresponds to the 1:1 association constant, K21 corresponds to the 2:1 receptor-sugar association constant, K12 corresponds to the 1:2 receptor-sugar association constant. β21, K11 x K21, β21, K11 x K12
-
12.
-
-
-
-
54
-
-
0004325424
-
-
University of Pittsburgh, Pittsburgh, PA
-
C. S. Wilcox, N. M. Glagovich, Program HOSTEST 5.6, University of Pittsburgh, Pittsburgh, PA, 1994.
-
(1994)
Program HOSTEST 5.6
-
-
Wilcox, C.S.1
Glagovich, N.M.2
|