-
1
-
-
0542421525
-
-
For some representative reviews, see: a
-
For some representative reviews, see: (a) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180.
-
(1998)
Acc. Chem. Res
, vol.31
, pp. 173-180
-
-
Gellman, S.H.1
-
2
-
-
2142742534
-
-
(b) Kirshenbaum, K.; Zuckermann, R. N.; Dill, K. A. Curr. Opin. Struct. Biol. 1999, 9, 530-535.
-
(1999)
Curr. Opin. Struct. Biol
, vol.9
, pp. 530-535
-
-
Kirshenbaum, K.1
Zuckermann, R.N.2
Dill, K.A.3
-
3
-
-
0035542909
-
-
(c) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4012.
-
(2001)
Chem. Rev
, vol.101
, pp. 3893-4012
-
-
Hill, D.J.1
Mio, M.J.2
Prince, R.B.3
Hughes, T.S.4
Moore, J.S.5
-
5
-
-
34247362490
-
-
(e) Goodman, C. M.; Choi, S.; Shandler, S.; DeGrado, W. F. Nat. Chem. Biol. 2007, 3, 252-262.
-
(2007)
Nat. Chem. Biol
, vol.3
, pp. 252-262
-
-
Goodman, C.M.1
Choi, S.2
Shandler, S.3
DeGrado, W.F.4
-
6
-
-
36849057990
-
-
Hecht, S, Huc, I, Eds, Wiley-VCH: Weinheim
-
Hecht, S., Huc, I., Eds. Foldamers: Structure, Properties, and Applications; Wiley-VCH: Weinheim, 2007.
-
(2007)
Foldamers: Structure, Properties, and Applications
-
-
-
7
-
-
57349134690
-
-
For a recent review, see
-
For a recent review, see: Horne, W. S.; Gellman, S. H. Acc. Chem. Res. 2008, 41, 1399-1408.
-
(2008)
Acc. Chem. Res
, vol.41
, pp. 1399-1408
-
-
Horne, W.S.1
Gellman, S.H.2
-
8
-
-
85023346540
-
-
For some other examples of heterogeneous foldamers, see: a
-
For some other examples of heterogeneous foldamers, see: (a) Hagihara, M.; Anthony, N. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6568-6570.
-
(1992)
J. Am. Chem. Soc
, vol.114
, pp. 6568-6570
-
-
Hagihara, M.1
Anthony, N.J.2
Stout, T.J.3
Clardy, J.4
Schreiber, S.L.5
-
9
-
-
0031468514
-
-
(b) Krauthäuser, S.; Christianson, L. A.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1997, 119, 11719-11720.
-
(1997)
J. Am. Chem. Soc
, vol.119
, pp. 11719-11720
-
-
Krauthäuser, S.1
Christianson, L.A.2
Powell, D.R.3
Gellman, S.H.4
-
10
-
-
0034710480
-
-
(c) Huck, B. R.; Fisk, J. D.; Gellman, S. H. Org. Lett. 2000, 2, 2607-2610.
-
(2000)
Org. Lett
, vol.2
, pp. 2607-2610
-
-
Huck, B.R.1
Fisk, J.D.2
Gellman, S.H.3
-
11
-
-
0035886802
-
-
(d) Gong, B. Chem.-Eur. J. 2001, 7, 4336-4342.
-
(2001)
Chem.-Eur. J
, vol.7
, pp. 4336-4342
-
-
Gong, B.1
-
12
-
-
0036420399
-
-
(e) Gopi, H. N.; Roy, R. S.; Raghothama, S. R.; Karle, I. L.; Balaram, P. Helv. Chim. Acta 2002, 85, 3313-3330.
-
(2002)
Helv. Chim. Acta
, vol.85
, pp. 3313-3330
-
-
Gopi, H.N.1
Roy, R.S.2
Raghothama, S.R.3
Karle, I.L.4
Balaram, P.5
-
15
-
-
64349100980
-
-
(h) Ananda, K.; Vasudev, P. G.; Sengupta, A.; Raja, K. M. P.; Baldauf, C.; Günther, R.; Hofmann, H. J. J. Org. Chem. 2006, 71, 1200-1208.
-
(2006)
J. Org. Chem
, vol.71
, pp. 1200-1208
-
-
Ananda, K.1
Vasudev, P.G.2
Sengupta, A.3
Raja, K.M.P.4
Baldauf, C.5
Günther, R.6
Hofmann, H.J.7
-
16
-
-
33750999348
-
-
(i) Sharma, G. V. M.; Jadhav, V. B.; Ramakrishna, K. V. S.; Jayaprakash, P.; Narsimulu, K.; Subash, V.; Kunwar, A. C. J. Am. Chem. Soc. 2006, 128, 14657-14668.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 14657-14668
-
-
Sharma, G.V.M.1
Jadhav, V.B.2
Ramakrishna, K.V.S.3
Jayaprakash, P.4
Narsimulu, K.5
Subash, V.6
Kunwar, A.C.7
-
17
-
-
36549056638
-
-
(j) Rodriguez, J. M.; Hamilton, A. D. Angew. Chem., Int. Ed. 2007, 46, 8614-8617.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 8614-8617
-
-
Rodriguez, J.M.1
Hamilton, A.D.2
-
20
-
-
33745713592
-
-
(m) Elliott, E. L.; Ray, C. R.; Kraft, S.; Atkins, J. R.; Moore, J. S. J. Org. Chem. 2006, 71, 5282-5290.
-
(2006)
J. Org. Chem
, vol.71
, pp. 5282-5290
-
-
Elliott, E.L.1
Ray, C.R.2
Kraft, S.3
Atkins, J.R.4
Moore, J.S.5
-
23
-
-
33846180694
-
-
(c) Zhao, Y.; Zhong, Z.; Ryu, E.-H. J. Am. Chem. Soc. 2007, 129, 218-225.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 218-225
-
-
Zhao, Y.1
Zhong, Z.2
Ryu, E.-H.3
-
25
-
-
64349099458
-
-
A longer oligocholate has more polar groups, which can concentrate the polar solvent more effectively into the hydrophilic interior of the folded helix. These polar solvent molecules in turn can solvate the introverted hydroxyl groups of the cholates more effectively in a nonpolar environment
-
A longer oligocholate has more polar groups, which can concentrate the polar solvent more effectively into the hydrophilic interior of the folded helix. These polar solvent molecules in turn can solvate the introverted hydroxyl groups of the cholates more effectively in a nonpolar environment.
-
-
-
-
26
-
-
64349104609
-
-
The longest oligocholate synthesized previously was a heptamer ref 5a
-
The longest oligocholate synthesized previously was a heptamer (ref 5a).
-
-
-
-
27
-
-
64349115177
-
-
The lack of reactivity in the terminal groups (azide or methyl ester) of 4 is peculiar. The compound is not expected to fold in the solvents used for the reactions. Our current hypothesis is that the curvature in the repeat unit makes an oligocholate curl back as the chain lengthens. Such a structure is disordered, different from the folded helix formed in special solvent mixtures. Derived from the monomer curvature, this curling back probably has little dependence on the solvents, should increase rapidly with an increase of the chain length, and may have buried the terminal groups of 4 to shield them from the chemical reagents. Unfortunately, the solubility of the oligocholates in the folding solvents (e.g, 2:1 hexane/EA with a few percent MeOH) is insufficient for us to test whether the reactivity is enhanced in the folding conditions. Further study is underway to investigate this effect
-
The lack of reactivity in the terminal groups (azide or methyl ester) of 4 is peculiar. The compound is not expected to fold in the solvents used for the reactions. Our current hypothesis is that the curvature in the repeat unit makes an oligocholate "curl back" as the chain lengthens. Such a structure is disordered, different from the folded helix formed in special solvent mixtures. Derived from the monomer curvature, this "curling back" probably has little dependence on the solvents, should increase rapidly with an increase of the chain length, and may have buried the terminal groups of 4 to shield them from the chemical reagents. Unfortunately, the solubility of the oligocholates in the folding solvents (e.g., 2:1 hexane/EA with a few percent MeOH) is insufficient for us to test whether the reactivity is enhanced in the folding conditions. Further study is underway to investigate this effect.
-
-
-
-
28
-
-
0000096835
-
-
For several reviews on click chemistry, see: a
-
For several reviews on "click" chemistry, see: (a) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021.
-
(2001)
Angew. Chem., Int. Ed
, vol.40
, pp. 2004-2021
-
-
Kolb, H.C.1
Finn, M.G.2
Sharpless, K.B.3
-
34
-
-
37249012927
-
-
For recent examples of foldamers prepared by click chemistry, see: a
-
For recent examples of foldamers prepared by "click" chemistry, see: (a) Meudtner, R. M.; Ostermeier, M.; Goddard, R.; Limberg, C.; Hecht, S. Chem.-Eur. J. 2007, 13, 9834-9840.
-
(2007)
Chem.-Eur. J
, vol.13
, pp. 9834-9840
-
-
Meudtner, R.M.1
Ostermeier, M.2
Goddard, R.3
Limberg, C.4
Hecht, S.5
-
35
-
-
34548166045
-
-
(b) Holub, J. M.; Jang, H.; Kirshenbaum, K. Org. Lett. 2007, 9, 3275-3278.
-
(2007)
Org. Lett
, vol.9
, pp. 3275-3278
-
-
Holub, J.M.1
Jang, H.2
Kirshenbaum, K.3
-
36
-
-
45549102695
-
-
(c) Juwarker, H.; Lenhardt, J. M.; Pham, D. M.; Craig, S. L. Angew. Chem., Int. Ed. 2008, 40, 3740-3743.
-
(2008)
Angew. Chem., Int. Ed
, vol.40
, pp. 3740-3743
-
-
Juwarker, H.1
Lenhardt, J.M.2
Pham, D.M.3
Craig, S.L.4
-
37
-
-
51749108427
-
-
(d) Meudtner, R. M.; Hecht, S. Angew. Chem., Int. Ed. 2008, 47, 4926-4930.
-
(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 4926-4930
-
-
Meudtner, R.M.1
Hecht, S.2
-
39
-
-
9344256088
-
-
For examples of using click chemistry on dendrimers or polymers, see: (a) Helms, B, Mynar, J. L, Hawker, C. J, Fréchet, J. M. J. J. Am. Chem. Soc. 2004, 126, 15020-15021
-
For examples of using "click" chemistry on dendrimers or polymers, see: (a) Helms, B.; Mynar, J. L.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 2004, 126, 15020-15021.
-
-
-
-
40
-
-
19744370243
-
-
(b) Parrish, B.; Breitenkamp, R. B.; Emrick, T. J. Am. Chem. Soc. 2005, 127, 7404-7410.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 7404-7410
-
-
Parrish, B.1
Breitenkamp, R.B.2
Emrick, T.3
-
41
-
-
33646513502
-
-
(c) Diaz, D. D.; Rajagopal, K.; Strable, E.; Schneider, J.; Finn, M. G. J. Am. Chem. Soc. 2006, 128, 6056-6057.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 6056-6057
-
-
Diaz, D.D.1
Rajagopal, K.2
Strable, E.3
Schneider, J.4
Finn, M.G.5
-
42
-
-
33748340641
-
-
(d) White, M. A.; Johnson, J. A.; Koberstein, J. T.; Turro, N. J. J. Am. Chem. Soc. 2006, 128, 11356-11357.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 11356-11357
-
-
White, M.A.1
Johnson, J.A.2
Koberstein, J.T.3
Turro, N.J.4
-
43
-
-
33748368270
-
-
(e) Whittaker, M. R.; Urbani, C. N.; Monteiro, M. J. J. Am. Chem. Soc. 2006, 128, 11360-11361.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 11360-11361
-
-
Whittaker, M.R.1
Urbani, C.N.2
Monteiro, M.J.3
-
44
-
-
18244371903
-
-
This condition previously afforded 1, 4-triazoles exclusively in our synthesis of water-soluble calixarenes; see: Ryu, E.-H, Zhao, Y. Org. Lett. 2005, 7, 1035-1037
-
This condition previously afforded 1, 4-triazoles exclusively in our synthesis of water-soluble calixarenes; see: Ryu, E.-H.; Zhao, Y. Org. Lett. 2005, 7, 1035-1037.
-
-
-
-
45
-
-
1842427379
-
-
Brady, P. A.; Bonar-Law, R. P.; Rowan, S. J.; Suckling, C. J.; Sanders, J. K. M. Chem. Commun. 1996, 319-320.
-
(1996)
Chem. Commun
, pp. 319-320
-
-
Brady, P.A.1
Bonar-Law, R.P.2
Rowan, S.J.3
Suckling, C.J.4
Sanders, J.K.M.5
-
46
-
-
64349106671
-
-
Folding of an oligocholate requires the phase separation of the polar solvent (MeOH) into the hydrophilic cavity in the folded helix. The phase separation of methanol is easier with hexane in the solvent because hexane is immiscible with methanol but EA is
-
Folding of an oligocholate requires the phase separation of the polar solvent (MeOH) into the hydrophilic cavity in the folded helix. The phase separation of methanol is easier with hexane in the solvent because hexane is immiscible with methanol but EA is.
-
-
-
-
48
-
-
0029653906
-
-
Chan, H. S.; Bromberg, S.; Dill, K. A. Philos. Trans. R. Soc. London B 1995, 348, 61-70.
-
(1995)
Philos. Trans. R. Soc. London B
, vol.348
, pp. 61-70
-
-
Chan, H.S.1
Bromberg, S.2
Dill, K.A.3
-
49
-
-
64349122424
-
-
The plateaus on the left and the right side of the titration curve generally correspond to the fully folded and the fully unfolded state for a two-state transition
-
The plateaus on the left and the right side of the titration curve generally correspond to the fully folded and the fully unfolded state for a two-state transition.
-
-
-
-
50
-
-
0033531714
-
-
Prince, R. B.; Saven, J. G.; Wolynes, P. G.; Moore, J. S. J. Am. Chem. Soc. 1999, 121, 3114-3121.
-
(1999)
J. Am. Chem. Soc
, vol.121
, pp. 3114-3121
-
-
Prince, R.B.1
Saven, J.G.2
Wolynes, P.G.3
Moore, J.S.4
-
51
-
-
64349122198
-
-
Another possible reason is the flexibility introduced by the aspartatetriazole linker s
-
Another possible reason is the flexibility introduced by the aspartatetriazole linker (s).
-
-
-
-
52
-
-
84889454714
-
-
This is probably because solvophobic forces do not require precise alignment of functional groups to be effective; see: Zhao, Y, Moore, J. S. In Foldamers; Hecht, S, Huc, I, Eds, Wiley-VCH: Weinheim, 2007; pp 75-108
-
This is probably because solvophobic forces do not require precise alignment of functional groups to be effective; see: Zhao, Y.; Moore, J. S. In Foldamers; Hecht, S., Huc, I., Eds.; Wiley-VCH: Weinheim, 2007; pp 75-108.
-
-
-
|