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33745502124
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For reviews of constrained peptide mimics, see: (a) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267; (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720; (c) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854; (d) Goodman, M.; Zhang, J. Chemtracts-Org. Chem. 1997, 10, 629-645.
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7
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For reviews of constrained peptide mimics, see: (a) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267; (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720; (c) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854; (d) Goodman, M.; Zhang, J. Chemtracts-Org. Chem. 1997, 10, 629-645.
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Gante, J.1
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8
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For reviews of constrained peptide mimics, see: (a) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267; (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720; (c) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854; (d) Goodman, M.; Zhang, J. Chemtracts-Org. Chem. 1997, 10, 629-645.
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Hanessian, S.1
McNaughton-Smith, G.2
Lombart, H.-G.3
Lubell, W.D.4
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9
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0000362486
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For reviews of constrained peptide mimics, see: (a) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267; (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720; (c) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854; (d) Goodman, M.; Zhang, J. Chemtracts-Org. Chem. 1997, 10, 629-645.
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Goodman, M.1
Zhang2
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14
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85030942777
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3 arised with respect to polar solvents such as water. Furthermore, the behaviour of this system in vacuo resulted very similar with that observed in chloroform, since there are many low-energy reverse-turn conformers with γ- or β-II′ turns. Moreover, in chloroform there is an increased population of the γ-turn conformers over the β-II′.
-
3 arised with respect to polar solvents such as water. Furthermore, the behaviour of this system in vacuo resulted very similar with that observed in chloroform, since there are many low-energy reverse-turn conformers with γ- or β-II′ turns. Moreover, in chloroform there is an increased population of the γ-turn conformers over the β-II′.
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21
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37049107435
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Itsuni S., Nakano M., Miyazaki K., Masuda H., Ito K., Hirao A., Nakahama S. J. Chem. Soc., Perkin Trans. 1. 1985;2039-2044.
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0033027365
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Grigg R., Hargreves S., Redpath J., Turchi S., Yoganathan G. Synthesis. 1999;441-446.
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Synthesis
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Chang, G.7
Hendrickson, T.8
Still, W.C.9
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35
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0028354084
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Analogous effects due to chelation were described for reductions of 2-acyloxazolidines. See, for example: (a) Colombo, L.; Di Giacomo, M.; Brusotti, G.; Delogu, G. Tetrahedron Lett. 1994, 35, 2063-2066; (b) Agami, C.; Couty, F. ; Lequesne, C. Tetrahedron, 1995, 51, 4043-4056.
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Colombo, L.1
Di Giacomo, M.2
Brusotti, G.3
Delogu, G.4
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36
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0028955943
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Analogous effects due to chelation were described for reductions of 2-acyloxazolidines. See, for example: (a) Colombo, L.; Di Giacomo, M.; Brusotti, G.; Delogu, G. Tetrahedron Lett. 1994, 35, 2063-2066; (b) Agami, C.; Couty, F. ; Lequesne, C. Tetrahedron, 1995, 51, 4043-4056.
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-
Agami, C.1
Couty, F.2
Lequesne, C.3
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37
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85030952616
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Significant calculated data for conformations A, B and C. A: d(HO)=1.942 Å. A. (H-3)-(C-3)-(C-1″)-(NH)=-107.8°; (H-3)-(C-3)-(C-1″)- (C-2″)=71.3°; (C-2)-(N-1)-(C-1′)-(H-1′)=-49.0°; (C-5)-(N-1)-(C-1′)-(C-2′)=18.4°. B: (H-3)-(C-3)-(C-1″)-(C- 2″)=81.8°; (H-3)-(C-3)-(C-1″)-(NH)=24.3°; (C-2)-(N-1)-(C-1′)-(H-1′)=-50.5°; (C-5)-(N-1)-(C-1′)-(C- 2′)=15.9°. C: (H-3)-(C-3)-(C-1″)-(C-2″)=-61.5°; (H-3)-(C-3)-(C-1″)-(NH)=117.0°; (C-2)-(N-1)-(C-1′)-(H-1′)= -48.2°; (C-5)-(N-1)-(C-1′)-(C-2′)=186.0°.
-
Significant calculated data for conformations A, B and C. A: d(HO)=1.942 Å. A. (H-3)-(C-3)-(C-1″)-(NH)=-107.8°; (H-3)-(C-3)-(C-1″)- (C-2″)=71.3°; (C-2)-(N-1)-(C-1′)-(H-1′)=-49.0°; (C-5)-(N-1)-(C-1′)-(C-2′)=18.4°. B: (H-3)-(C-3)-(C-1″)-(C- 2″)=81.8°; (H-3)-(C-3)-(C-1″)-(NH)=24.3°; (C-2)-(N-1)-(C-1′)-(H-1′)=-50.5°; (C-5)-(N-1)-(C-1′)-(C- 2′)=15.9°. C: (H-3)-(C-3)-(C-1″)-(C-2″)=-61.5°; (H-3)-(C-3)-(C-1″)-(NH)=117.0°; (C-2)-(N-1)-(C-1′)-(H-1′)= -48.2°; (C-5)-(N-1)-(C-1′)-(C-2′)=186.0°.
-
-
-
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39
-
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85030937531
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-
Significant calculated data for conformations D, E and F. D: d(HO)=1.990 Å. A. (H-3)-(C-3)-(C-1″)-(NH)=-111.7°; (H-3)-(C-3)-(C-1″)- (C-2″)=68.3°; (C-2)-(N-1)-(C-1′)-(H-1′)=-47.4°; (C-5)-(N-1)-(C-1′)-(C-2′)=19.0°. E: (H-3)-(C-3)-(C-1″)- (NH)=6.5°; (H-3)-(C-3)-(C-1″)-(C-2″)=125.5°; (C-2)-(N-1)-(C-1′)-(H-1′)=-48.6°; (C-5)-(N-1)-(C-1′)-(C- 2′)=181.0°. F: (H-3)-(C-3)-(C-1″)-(NH)=121.9°; (H-3)-(C-3)-(C-1″)-(C-2″)=-56.8°; (C-2)-(N-1)-(C-1′)-(H- 1′)=-46.8° (C-5)-(N-1)-(C-1′)-(C-2′)=19.6°.
-
Significant calculated data for conformations D, E and F. D: d(HO)=1.990 Å. A. (H-3)-(C-3)-(C-1″)-(NH)=-111.7°; (H-3)-(C-3)-(C-1″)- (C-2″)=68.3°; (C-2)-(N-1)-(C-1′)-(H-1′)=-47.4°; (C-5)-(N-1)-(C-1′)-(C-2′)=19.0°. E: (H-3)-(C-3)-(C-1″)- (NH)=6.5°; (H-3)-(C-3)-(C-1″)-(C-2″)=125.5°; (C-2)-(N-1)-(C-1′)-(H-1′)=-48.6°; (C-5)-(N-1)-(C-1′)-(C- 2′)=181.0°. F: (H-3)-(C-3)-(C-1″)-(NH)=121.9°; (H-3)-(C-3)-(C-1″)-(C-2″)=-56.8°; (C-2)-(N-1)-(C-1′)-(H- 1′)=-46.8° (C-5)-(N-1)-(C-1′)-(C-2′)=19.6°.
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40
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84881454506
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0Gaussian Inc., Pittsburgh, PA
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Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, Jr., J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millan, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Patersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malik, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzales, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. Gaussian 98, Revision A.9, Gaussian Inc., Pittsburgh, PA, 1998.
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Frisch, M.J.1
Trucks, G.W.2
Schlegel, H.B.3
Scuseria, G.E.4
Robb, M.A.5
Cheeseman, J.R.6
Zakrzewski, V.G.7
Montgomery Jr., J.A.8
Stratmann, R.E.9
Burant, J.C.10
Dapprich, S.11
Millan, J.M.12
Daniels, A.D.13
Kudin, K.N.14
Strain, M.C.15
Farkas, O.16
Tomasi, J.17
Barone, V.18
Cossi, M.19
Cammi, R.20
Mennucci, B.21
Pomelli, C.22
Adamo, C.23
Clifford, S.24
Ochterski, J.25
Patersson, G.A.26
Ayala, P.Y.27
Cui, Q.28
Morokuma, K.29
Malik, D.K.30
Rabuck, A.D.31
Raghavachari, K.32
Foresman, J.B.33
Cioslowski, J.34
Ortiz, J.V.35
Baboul, A.G.36
Stefanov, B.B.37
Liu, G.38
Liashenko, A.39
Piskorz, P.40
Komaromi, I.41
Gomperts, R.42
Martin, R.L.43
Fox, D.J.44
Keith, T.45
Al-Laham, M.A.46
Peng, C.Y.47
Nanayakkara, A.48
Challacombe, M.49
Gill, P.M.W.50
Johnson, B.51
Chen, W.52
Wong, M.W.53
Andres, J.L.54
Gonzales, C.55
Head-Gordon, M.56
Replogle, E.S.57
Pople, J.58
more..
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42
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85030951660
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2 (ethenyl): 5.12-5.24; CH̄ (ethenyl): 5.85; NH̄: 6.56.
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2 (ethenyl): 5.12-5.24; CH̄ (ethenyl): 5.85; NH̄: 6.56.
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49
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33750181960
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McWeeny R. Phys. Rev. 126:1962;1024-1028.
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