-
2
-
-
0037126686
-
-
W. J. Wedemeyer, E. Welker, H. A. Scheraga, Biochemistry 2002, 41, 14637-14644
-
(2002)
Biochemistry
, vol.41
, pp. 14637-14644
-
-
Wedemeyer, W.J.1
Welker, E.2
Scheraga, H.A.3
-
4
-
-
34548660854
-
-
K. P. Lu, G. Finn, T. H. Lee, L. Nicholson, Nat. Chem. Biol. 2007, 3, 619-629.
-
(2007)
Nat. Chem. Biol.
, vol.3
, pp. 619-629
-
-
Lu, K.P.1
Finn, G.2
Lee, T.H.3
Nicholson, L.4
-
6
-
-
45949083738
-
-
T. Steiner, P. Hess, J. H. Bae, B. Wiltschi, L. Moroder, N. Budisa, PloS ONE 2008, 3, e1680
-
(2008)
PloS ONE
, vol.3
-
-
Steiner, T.1
Hess, P.2
Bae, J.H.3
Wiltschi, B.4
Moroder, L.5
Budisa, N.6
-
8
-
-
0032537113
-
-
S. K. Holmgren, K. M. Taylor, L. E. Bretscher, R. T. Raines, Nature 1998, 392, 666-667.
-
(1998)
Nature
, vol.392
, pp. 666-667
-
-
Holmgren, S.K.1
Taylor, K.M.2
Bretscher, L.E.3
Raines, R.T.4
-
9
-
-
41449083869
-
-
For examples, see
-
For examples, see: F.W. Kotch, I. A. Guzei, R. T. Raines, J. Am. Chem. Soc. 2008, 130, 2952
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 2952
-
-
Kotch, F.W.1
Guzei, I.A.2
Raines, R.T.3
-
10
-
-
70349934781
-
-
S. A. Cadamuro, R. Reichhold, U. Kusebauch, H.-J. Musiol, C. Renner, P. Tavan, L. Moroder, Angew. Chem. 2008, 120, 2174-2177
-
(2008)
Angew. Chem.
, vol.120
, pp. 2174-2177
-
-
Cadamuro, S.A.1
Reichhold, R.2
Kusebauch, U.3
Musiol, H.-J.4
Renner, C.5
Tavan, P.6
Moroder, L.7
-
11
-
-
41949089855
-
-
Angew. Chem. Int. Ed. 2008, 47, 2143-2146
-
(2008)
Angew. Chem. Int. Ed.
, vol.47
, pp. 2143-2146
-
-
-
12
-
-
70349932790
-
-
N.W. Owens, A. Lee, K. Marat, F. Schweizer, Chem. Eur. J. 2009, 15, 10649-10657
-
(2009)
Chem. Eur. J.
, vol.15
, pp. 10649-10657
-
-
Owens, N.W.1
Lee, A.2
Marat, K.3
Schweizer, F.4
-
13
-
-
33745663038
-
-
M. D. Shoulders, J. A. Hodges, R. T. Raines, J. Am. Chem. Soc. 2006, 128, 8112-8113
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 8112-8113
-
-
Shoulders, M.D.1
Hodges, J.A.2
Raines, R.T.3
-
14
-
-
20544453286
-
-
K. M. Thomas, D. Naduthambi, G. Tririya, N. J. Zondlo, Org. Lett. 2005, 7, 2397-2400
-
(2005)
Org. Lett.
, vol.7
, pp. 2397-2400
-
-
Thomas, K.M.1
Naduthambi, D.2
Tririya, G.3
Zondlo, N.J.4
-
15
-
-
0001370761
-
-
C. Renner, S. Alefelder, J. H. Bae, N. Budisa, R. Huber, L. Moroder, Angew. Chem. 2001, 113, 949-951
-
(2001)
Angew. Chem.
, vol.113
, pp. 949-951
-
-
Renner, C.1
Alefelder, S.2
Bae, J.H.3
Budisa, N.4
Huber, R.5
Moroder, L.6
-
18
-
-
0000617719
-
-
E. Beausoleil, R. Sharma, S.W. Michnick, W. D. Lubell, J. Org. Chem. 1998, 63, 6572-6578
-
(1998)
J. Org. Chem.
, vol.63
, pp. 6572-6578
-
-
Beausoleil, E.1
Sharma, R.2
Michnick, S.W.3
Lubell, W.D.4
-
19
-
-
0029927552
-
-
T. P. Curran, N. M. Chandler, R. J. Kennedy, M. T. Keaney, Tetrahedron Lett. 1996, 37, 1933-1936.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 1933-1936
-
-
Curran, T.P.1
Chandler, N.M.2
Kennedy, R.J.3
Keaney, M.T.4
-
20
-
-
47749103012
-
-
M. D. Shoulders, I. A. Guzei, R. T. Raines, Biopolymers 2008, 89, 443
-
(2008)
Biopolymers
, vol.89
, pp. 443
-
-
Shoulders, M.D.1
Guzei, I.A.2
Raines, R.T.3
-
21
-
-
14944366759
-
-
C. L. Jenkins, A. I. McCloskey, I. A. Guezei, E. S. Eberhardt, R. T. Raines, Biopolymers 2005, 80, 1-8
-
(2005)
Biopolymers
, vol.80
, pp. 1-8
-
-
Jenkins, C.L.1
McCloskey, A.I.2
Guezei, I.A.3
Eberhardt, E.S.4
Raines, R.T.5
-
22
-
-
23044447161
-
-
A.M. P. Koskinen, J. Heliaja, E. T. T. Kumpulainen, J. Koivisto, H. Mansikkamaeki, K. Rissanen, J. Org. Chem. 2005, 70, 6447-6453
-
(2005)
J. Org. Chem.
, vol.70
, pp. 6447-6453
-
-
Koskinen, A.M.P.1
Heliaja, J.2
Kumpulainen, E.T.T.3
Koivisto, J.4
Mansikkamaeki, H.5
Rissanen, K.6
-
23
-
-
0037139532
-
-
M. L. DeRider, S. J. Wilkens, M. J. Waddell, L. E. Bretscher, F. Weinhold, R. T. Raines, J. Am. Chem. Soc. 2002, 124, 2497-2505
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 2497-2505
-
-
DeRider, M.L.1
Wilkens, S.J.2
Waddell, M.J.3
Bretscher, L.E.4
Weinhold, F.5
Raines, R.T.6
-
24
-
-
0035977605
-
-
L. E. Bretscher, C. L. Jenkins, K. M. Taylor, M. L. DeRider, R. T. Raines, J. Am. Chem. Soc. 2001, 123, 777-778.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 777-778
-
-
Bretscher, L.E.1
Jenkins, C.L.2
Taylor, K.M.3
DeRider, M.L.4
Raines, R.T.5
-
25
-
-
33750986797
-
-
L.-S. Sonntag, S. Schweizer, C. Ochsenfeld, H. Wennemers, J. Am. Chem. Soc. 2006, 128, 14697-14703.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 14697-14703
-
-
Sonntag, L.-S.1
Schweizer, S.2
Ochsenfeld, C.3
Wennemers, H.4
-
26
-
-
0029078444
-
-
P. H. Maccallum, R. Poet, E. J. Milner-White, J. Mol. Biol. 1995, 248, 374-384
-
(1995)
J. Mol. Biol.
, vol.248
, pp. 374-384
-
-
Maccallum, P.H.1
Poet, R.2
Milner-White, E.J.3
-
27
-
-
0029048210
-
-
P. H. Maccallum, R. Poet, E. J. Milner- White, J. Mol. Biol. 1995, 248, 361-373.
-
(1995)
J. Mol. Biol.
, vol.248
, pp. 361-373
-
-
Maccallum, P.H.1
Poet, R.2
Milner-White, E.J.3
-
28
-
-
67650547528
-
-
A. Choudhary, D. Gandla, G. R. Krow, R. T. Raines, J. Am. Chem. Soc. 2009, 131, 7244-7246
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 7244-7246
-
-
Choudhary, A.1
Gandla, D.2
Krow, G.R.3
Raines, R.T.4
-
31
-
-
57549105838
-
-
N. H. Shah, G. L. Butterfoss, K. Nguyen, B. Yoo, R. Bonneau, D. L. Rabenstein, K. Kirshenbaum, J. Am. Chem. Soc. 2008, 130, 16622-16632
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 16622-16632
-
-
Shah, N.H.1
Butterfoss, G.L.2
Nguyen, K.3
Yoo, B.4
Bonneau, R.5
Rabenstein, D.L.6
Kirshenbaum, K.7
-
32
-
-
34547491911
-
-
B. C. Gorske, B. L. Bastian, D. G. Geske, H. L. Blackwell, J. Am. Chem. Soc. 2007, 129, 8928-8929.
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 8928-8929
-
-
Gorske, B.C.1
Bastian, B.L.2
Geske, D.G.3
Blackwell, H.L.4
-
33
-
-
0027080914
-
-
E. J. Milner-White, L. H. Bell, P. H. Maccallum, J. Mol. Biol. 1992, 228, 725-734
-
(1992)
J. Mol. Biol.
, vol.228
, pp. 725-734
-
-
Milner-White, E.J.1
Bell, L.H.2
Maccallum, P.H.3
-
35
-
-
0026832808
-
-
The acetylated methyl esters were chosen as model systems in which H-bonding by a γ turn as observed in Ac-Pro-NHMe cannot occur
-
The acetylated methyl esters were chosen as model systems in which H-bonding by a γ turn as observed in Ac-Pro-NHMe cannot occur, G.-B. Liang, C. J. Rito, S. H. Gellman, Biopolymers 1992, 32, 293 - 301.
-
(1992)
Biopolymers
, vol.32
, pp. 293-301
-
-
Liang, G.-B.1
Rito, C.J.2
Gellman, S.H.3
-
36
-
-
33947086888
-
-
H. B. Bürgi, J. D. Dunitz, E. Shefter, J. Am. Chem. Soc. 1973, 95, 5065-5067.
-
(1973)
J. Am. Chem. Soc.
, vol.95
, pp. 5065-5067
-
-
Bürgi, H.B.1
Dunitz, J.D.2
Shefter, E.3
-
37
-
-
0029927552
-
-
For previous discussions on the effect of intramolecular Hbonding on the conformation of proline, see: refs[3c, h, 4e] and
-
For previous discussions on the effect of intramolecular Hbonding on the conformation of proline, see: refs. c, h, 4eand T. P. Curran, N. M. Chandler, R. J. Kennedy, M. T. Keaney, Tetrahedron Lett. 1996, 37, 1933-1936
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 1933-1936
-
-
Curran, T.P.1
Chandler, N.M.2
Kennedy, R.J.3
Keaney, M.T.4
-
38
-
-
84961973279
-
-
R. Improta, C. Benzi, V. Barone, J. Am. Chem. Soc. 2001, 123, 12568-12577
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 12568-12577
-
-
Improta, R.1
Benzi, C.2
Barone, V.3
-
39
-
-
13844320101
-
-
C. M. Taylor, R. Hardré, P. J. B. Edwards, J. Org. Chem. 2005, 70, 1306-1315
-
(2005)
J. Org. Chem.
, vol.70
, pp. 1306-1315
-
-
Taylor, C.M.1
Hardré, R.2
Edwards, P.J.B.3
-
40
-
-
65949111068
-
-
K. Zhang, R. B. Teklebrhan, G. Schreckenbach, S. Wetmore, F. Schweizer, J. Org. Chem. 2009, 74, 3735-3743.
-
(2009)
J. Org. Chem.
, vol.74
, pp. 3735-3743
-
-
Zhang, K.1
Teklebrhan, R.B.2
Schreckenbach, G.3
Wetmore, S.4
Schweizer, F.5
-
41
-
-
77956028347
-
-
3 (refs. [3-5])
-
3 (refs. [3-5]).
-
-
-
-
42
-
-
77956013750
-
-
The trans and cis isomers were assigned based on NOEs between the protons of the acetyl group and those at Cδ and Cα, respectively
-
The trans and cis isomers were assigned based on NOEs between the protons of the acetyl group and those at Cδ and Cα, respectively.
-
-
-
-
43
-
-
77956046623
-
-
Conformational searches and ab initio calculations were performed by using the Spartan'02 package (Spartan'02, Wavefunction, Inc., Irvine, CA) and a development version of the QChem program package, respectively
-
Conformational searches and ab initio calculations were performed by using the Spartan'02 package (Spartan'02, Wavefunction, Inc., Irvine, CA) and a development version of the QChem program package (http://www.q-chem.com), respectively.
-
-
-
-
44
-
-
77956051933
-
-
See the Supporting Information for details
-
See the Supporting Information for details.
-
-
-
-
46
-
-
33751157732
-
-
P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch, J. Chem. Phys. 1994, 98, 11623-11627
-
(1994)
J. Chem. Phys.
, vol.98
, pp. 11623-11627
-
-
Stephens, P.J.1
Devlin, F.J.2
Chabalowski, C.F.3
Frisch, M.J.4
-
47
-
-
0347170005
-
-
W. J. Hehre, R. Ditchfield, J. A. Pople, J. Chem. Phys. 1972, 56, 2257-2261
-
(1972)
J. Chem. Phys.
, vol.56
, pp. 2257-2261
-
-
Hehre, W.J.1
Ditchfield, R.2
Pople, J.A.3
-
49
-
-
22944484208
-
-
K. Eichkorn, O. Treutler, H. Oehm, M. Häser, R. Ahlrichs, Chem. Phys. Lett. 1995, 240, 283-289
-
(1995)
Chem. Phys. Lett.
, vol.240
, pp. 283-289
-
-
Eichkorn, K.1
Treutler, O.2
Oehm, H.3
Häser, M.4
Ahlrichs, R.5
-
50
-
-
0039209924
-
-
A. Schäfer, C. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829-5835.
-
(1994)
J. Chem. Phys.
, vol.100
, pp. 5829-5835
-
-
Schäfer, A.1
Huber, C.2
Ahlrichs, R.3
-
51
-
-
77956043757
-
-
The existence of the hydrogen bond in 2S-4S is further supported by the larger vicinal NH-Hg coupling constants in the trans conformer of 2S-4S (7.9-8.6 Hz) compared to those observed for the cis conformer (5.4-6.5 Hz) as well as those of 2R-4R (6.5-6.8 Hz, both conformers). A large coupling constant is expected for a C4-endo conformation with a fixed dihedral angle Hγ-C-N-H close to 180° (see Scheme 2, right). Crystal structures of 1S and 2S are controlled by intermolecular hydrogen bonds and therefore not representative of their conformations in solution phase
-
The existence of the hydrogen bond in 2S-4S is further supported by the larger vicinal NH-Hg coupling constants in the trans conformer of 2S-4S (7.9-8.6 Hz) compared to those observed for the cis conformer (5.4-6.5 Hz) as well as those of 2R-4R (6.5-6.8 Hz, both conformers). A large coupling constant is expected for a C4-endo conformation with a fixed dihedral angle Hγ-C-N-H close to 180° (see Scheme 2, right). Crystal structures of 1S and 2S are controlled by intermolecular hydrogen bonds and therefore not representative of their conformations in solution phase.
-
-
-
-
52
-
-
0027624925
-
-
F. Rabanal, M. D. Ludevid, M. Pons, E. Giralt, Biopolymers 1993, 33, 1019-1028.
-
(1993)
Biopolymers
, vol.33
, pp. 1019-1028
-
-
Rabanal, F.1
Ludevid, M.D.2
Pons, M.3
Giralt, E.4
-
53
-
-
70350267056
-
-
M. Kuemin, S. Schweizer, C. Ochsenfeld, H. Wennemers, J. Am. Chem. Soc. 2009, 131, 15474-15 482
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 15474-15482
-
-
Kuemin, M.1
Schweizer, S.2
Ochsenfeld, C.3
Wennemers, H.4
-
54
-
-
66749111719
-
-
R. S. Erdmann, M. Kuemin, H. Wennemers, Chimia 2009, 63, 197-200
-
(2009)
Chimia
, vol.63
, pp. 197-200
-
-
Erdmann, R.S.1
Kuemin, M.2
Wennemers, H.3
-
55
-
-
33846415089
-
-
M. Kümin, L.-S. Sonntag, H. Wennemers, J. Am. Chem. Soc. 2007, 129, 466-467.
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 466-467
-
-
Kümin, M.1
Sonntag, L.-S.2
Wennemers, H.3
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