Conformational Analysis of Peptides and Pseudopeptides Incorporating an endo-(2S,3R)-Norborn-5-ene Residue as a Turn Inducer

Journal of Organic Chemistry

Volumn 63, Issue 5, 1998, Pages 1505-1513

  Jones, Iwan G ^a   Jones, Wyn ^b   North, Michael ^a  

^a BANGOR UNIVERSITY   (United Kingdom)

^b Peboc Div of Eastman Chemical Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001099564     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971766t     Document Type: Article

References (67)

1. Throughout this paper, all α-amino acids have the (S)-configuration.
2. For examples of β-turn and β-sheet mimics see: Biagini, S. C. G.; North, M. Amino Acids, Peptides and Proteins: Specialist Periodical Reports Vol. 27; (Davies, J. S., Ed.; The Royal Society of Chemistry: London, 1996; Chapter 3. Peptide Secondary Structure Mimetics: Tetrahedron Symposia in Print Number 50; Kahn, M., Ed. Tetrahedron 1993, 49, 3433-3689. Horwell, D. C.; Naylor, D.; Willems, H. M. G. Bioorg. Med. Chem. Lett. 1997, 7, 31. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847. Kobayashi, K; Granja, J. R.; Ghaddidri, M. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 95. Tsang, K. Y. T.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. Tsang, K. Y.; Diaz, H.; Smith, A. B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947. Giannis, A.; Kolter, T. Angew. Chem., Int Ed. Engl. 1993, 32, 1244. Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Ernest, I.; J. Kalvoda, J.; Rihs, G.; Mutter, M. Tetrahedron Lett. 1990, 31, 4011. Kemp, D. S.; Bowen, B. R.; Muendal, C. C. J. Org. Chem. 1990, 55, 4650. Kemp, D. S.; Stites, W. E. Tetrahedron Lett. 1988, 29, 5057. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5077. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081 and references cited in these papers.
3. For examples of β-turn and β-sheet mimics see: Biagini, S. C. G.; North, M. Amino Acids, Peptides and Proteins: Specialist Periodical Reports Vol. 27; (Davies, J. S., Ed.; The Royal Society of Chemistry: London, 1996; Chapter 3. Peptide Secondary Structure Mimetics: Tetrahedron Symposia in Print Number 50; Kahn, M., Ed. Tetrahedron 1993, 49, 3433-3689. Horwell, D. C.; Naylor, D.; Willems, H. M. G. Bioorg. Med. Chem. Lett. 1997, 7, 31. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847. Kobayashi, K; Granja, J. R.; Ghaddidri, M. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 95. Tsang, K. Y. T.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. Tsang, K. Y.; Diaz, H.; Smith, A. B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947. Giannis, A.; Kolter, T. Angew. Chem., Int Ed. Engl. 1993, 32, 1244. Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Ernest, I.; J. Kalvoda, J.; Rihs, G.; Mutter, M. Tetrahedron Lett. 1990, 31, 4011. Kemp, D. S.; Bowen, B. R.; Muendal, C. C. J. Org. Chem. 1990, 55, 4650. Kemp, D. S.; Stites, W. E. Tetrahedron Lett. 1988, 29, 5057. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5077. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081 and references cited in these papers.
4. For examples of β-turn and β-sheet mimics see: Biagini, S. C. G.; North, M. Amino Acids, Peptides and Proteins: Specialist Periodical Reports Vol. 27; (Davies, J. S., Ed.; The Royal Society of Chemistry: London, 1996; Chapter 3. Peptide Secondary Structure Mimetics: Tetrahedron Symposia in Print Number 50; Kahn, M., Ed. Tetrahedron 1993, 49, 3433-3689. Horwell, D. C.; Naylor, D.; Willems, H. M. G. Bioorg. Med. Chem. Lett. 1997, 7, 31. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847. Kobayashi, K; Granja, J. R.; Ghaddidri, M. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 95. Tsang, K. Y. T.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. Tsang, K. Y.; Diaz, H.; Smith, A. B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947. Giannis, A.; Kolter, T. Angew. Chem., Int Ed. Engl. 1993, 32, 1244. Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Ernest, I.; J. Kalvoda, J.; Rihs, G.; Mutter, M. Tetrahedron Lett. 1990, 31, 4011. Kemp, D. S.; Bowen, B. R.; Muendal, C. C. J. Org. Chem. 1990, 55, 4650. Kemp, D. S.; Stites, W. E. Tetrahedron Lett. 1988, 29, 5057. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5077. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081 and references cited in these papers.
5. For examples of β-turn and β-sheet mimics see: Biagini, S. C. G.; North, M. Amino Acids, Peptides and Proteins: Specialist Periodical Reports Vol. 27; (Davies, J. S., Ed.; The Royal Society of Chemistry: London, 1996; Chapter 3. Peptide Secondary Structure Mimetics: Tetrahedron Symposia in Print Number 50; Kahn, M., Ed. Tetrahedron 1993, 49, 3433-3689. Horwell, D. C.; Naylor, D.; Willems, H. M. G. Bioorg. Med. Chem. Lett. 1997, 7, 31. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847. Kobayashi, K; Granja, J. R.; Ghaddidri, M. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 95. Tsang, K. Y. T.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. Tsang, K. Y.; Diaz, H.; Smith, A. B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947. Giannis, A.; Kolter, T. Angew. Chem., Int Ed. Engl. 1993, 32, 1244. Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Ernest, I.; J. Kalvoda, J.; Rihs, G.; Mutter, M. Tetrahedron Lett. 1990, 31, 4011. Kemp, D. S.; Bowen, B. R.; Muendal, C. C. J. Org. Chem. 1990, 55, 4650. Kemp, D. S.; Stites, W. E. Tetrahedron Lett. 1988, 29, 5057. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5077. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081 and references cited in these papers.
6. For examples of β-turn and β-sheet mimics see: Biagini, S. C. G.; North, M. Amino Acids, Peptides and Proteins: Specialist Periodical Reports Vol. 27; (Davies, J. S., Ed.; The Royal Society of Chemistry: London, 1996; Chapter 3. Peptide Secondary Structure Mimetics: Tetrahedron Symposia in Print Number 50; Kahn, M., Ed. Tetrahedron 1993, 49, 3433-3689. Horwell, D. C.; Naylor, D.; Willems, H. M. G. Bioorg. Med. Chem. Lett. 1997, 7, 31. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847. Kobayashi, K; Granja, J. R.; Ghaddidri, M. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 95. Tsang, K. Y. T.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. Tsang, K. Y.; Diaz, H.; Smith, A. B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947. Giannis, A.; Kolter, T. Angew. Chem., Int Ed. Engl. 1993, 32, 1244. Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Ernest, I.; J. Kalvoda, J.; Rihs, G.; Mutter, M. Tetrahedron Lett. 1990, 31, 4011. Kemp, D. S.; Bowen, B. R.; Muendal, C. C. J. Org. Chem. 1990, 55, 4650. Kemp, D. S.; Stites, W. E. Tetrahedron Lett. 1988, 29, 5057. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5077. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081 and references cited in these papers.
7. For examples of β-turn and β-sheet mimics see: Biagini, S. C. G.; North, M. Amino Acids, Peptides and Proteins: Specialist Periodical Reports Vol. 27; (Davies, J. S., Ed.; The Royal Society of Chemistry: London, 1996; Chapter 3. Peptide Secondary Structure Mimetics: Tetrahedron Symposia in Print Number 50; Kahn, M., Ed. Tetrahedron 1993, 49, 3433-3689. Horwell, D. C.; Naylor, D.; Willems, H. M. G. Bioorg. Med. Chem. Lett. 1997, 7, 31. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847. Kobayashi, K; Granja, J. R.; Ghaddidri, M. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 95. Tsang, K. Y. T.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. Tsang, K. Y.; Diaz, H.; Smith, A. B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947. Giannis, A.; Kolter, T. Angew. Chem., Int Ed. Engl. 1993, 32, 1244. Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Ernest, I.; J. Kalvoda, J.; Rihs, G.; Mutter, M. Tetrahedron Lett. 1990, 31, 4011. Kemp, D. S.; Bowen, B. R.; Muendal, C. C. J. Org. Chem. 1990, 55, 4650. Kemp, D. S.; Stites, W. E. Tetrahedron Lett. 1988, 29, 5057. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5077. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081 and references cited in these papers.
8. For examples of β-turn and β-sheet mimics see: Biagini, S. C. G.; North, M. Amino Acids, Peptides and Proteins: Specialist Periodical Reports Vol. 27; (Davies, J. S., Ed.; The Royal Society of Chemistry: London, 1996; Chapter 3. Peptide Secondary Structure Mimetics: Tetrahedron Symposia in Print Number 50; Kahn, M., Ed. Tetrahedron 1993, 49, 3433-3689. Horwell, D. C.; Naylor, D.; Willems, H. M. G. Bioorg. Med. Chem. Lett. 1997, 7, 31. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847. Kobayashi, K; Granja, J. R.; Ghaddidri, M. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 95. Tsang, K. Y. T.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. Tsang, K. Y.; Diaz, H.; Smith, A. B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947. Giannis, A.; Kolter, T. Angew. Chem., Int Ed. Engl. 1993, 32, 1244. Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Ernest, I.; J. Kalvoda, J.; Rihs, G.; Mutter, M. Tetrahedron Lett. 1990, 31, 4011. Kemp, D. S.; Bowen, B. R.; Muendal, C. C. J. Org. Chem. 1990, 55, 4650. Kemp, D. S.; Stites, W. E. Tetrahedron Lett. 1988, 29, 5057. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5077. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081 and references cited in these papers.
9. For examples of β-turn and β-sheet mimics see: Biagini, S. C. G.; North, M. Amino Acids, Peptides and Proteins: Specialist Periodical Reports Vol. 27; (Davies, J. S., Ed.; The Royal Society of Chemistry: London, 1996; Chapter 3. Peptide Secondary Structure Mimetics: Tetrahedron Symposia in Print Number 50; Kahn, M., Ed. Tetrahedron 1993, 49, 3433-3689. Horwell, D. C.; Naylor, D.; Willems, H. M. G. Bioorg. Med. Chem. Lett. 1997, 7, 31. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847. Kobayashi, K; Granja, J. R.; Ghaddidri, M. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 95. Tsang, K. Y. T.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. Tsang, K. Y.; Diaz, H.; Smith, A. B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947. Giannis, A.; Kolter, T. Angew. Chem., Int Ed. Engl. 1993, 32, 1244. Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Ernest, I.; J. Kalvoda, J.; Rihs, G.; Mutter, M. Tetrahedron Lett. 1990, 31, 4011. Kemp, D. S.; Bowen, B. R.; Muendal, C. C. J. Org. Chem. 1990, 55, 4650. Kemp, D. S.; Stites, W. E. Tetrahedron Lett. 1988, 29, 5057. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5077. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081 and references cited in these papers.
10. For examples of β-turn and β-sheet mimics see: Biagini, S. C. G.; North, M. Amino Acids, Peptides and Proteins: Specialist Periodical Reports Vol. 27; (Davies, J. S., Ed.; The Royal Society of Chemistry: London, 1996; Chapter 3. Peptide Secondary Structure Mimetics: Tetrahedron Symposia in Print Number 50; Kahn, M., Ed. Tetrahedron 1993, 49, 3433-3689. Horwell, D. C.; Naylor, D.; Willems, H. M. G. Bioorg. Med. Chem. Lett. 1997, 7, 31. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847. Kobayashi, K; Granja, J. R.; Ghaddidri, M. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 95. Tsang, K. Y. T.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. Tsang, K. Y.; Diaz, H.; Smith, A. B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947. Giannis, A.; Kolter, T. Angew. Chem., Int Ed. Engl. 1993, 32, 1244. Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Ernest, I.; J. Kalvoda, J.; Rihs, G.; Mutter, M. Tetrahedron Lett. 1990, 31, 4011. Kemp, D. S.; Bowen, B. R.; Muendal, C. C. J. Org. Chem. 1990, 55, 4650. Kemp, D. S.; Stites, W. E. Tetrahedron Lett. 1988, 29, 5057. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5077. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081 and references cited in these papers.
11. For examples of β-turn and β-sheet mimics see: Biagini, S. C. G.; North, M. Amino Acids, Peptides and Proteins: Specialist Periodical Reports Vol. 27; (Davies, J. S., Ed.; The Royal Society of Chemistry: London, 1996; Chapter 3. Peptide Secondary Structure Mimetics: Tetrahedron Symposia in Print Number 50; Kahn, M., Ed. Tetrahedron 1993, 49, 3433-3689. Horwell, D. C.; Naylor, D.; Willems, H. M. G. Bioorg. Med. Chem. Lett. 1997, 7, 31. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847. Kobayashi, K; Granja, J. R.; Ghaddidri, M. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 95. Tsang, K. Y. T.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. Tsang, K. Y.; Diaz, H.; Smith, A. B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947. Giannis, A.; Kolter, T. Angew. Chem., Int Ed. Engl. 1993, 32, 1244. Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Ernest, I.; J. Kalvoda, J.; Rihs, G.; Mutter, M. Tetrahedron Lett. 1990, 31, 4011. Kemp, D. S.; Bowen, B. R.; Muendal, C. C. J. Org. Chem. 1990, 55, 4650. Kemp, D. S.; Stites, W. E. Tetrahedron Lett. 1988, 29, 5057. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5077. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081 and references cited in these papers.
12. For examples of β-turn and β-sheet mimics see: Biagini, S. C. G.; North, M. Amino Acids, Peptides and Proteins: Specialist Periodical Reports Vol. 27; (Davies, J. S., Ed.; The Royal Society of Chemistry: London, 1996; Chapter 3. Peptide Secondary Structure Mimetics: Tetrahedron Symposia in Print Number 50; Kahn, M., Ed. Tetrahedron 1993, 49, 3433-3689. Horwell, D. C.; Naylor, D.; Willems, H. M. G. Bioorg. Med. Chem. Lett. 1997, 7, 31. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847. Kobayashi, K; Granja, J. R.; Ghaddidri, M. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 95. Tsang, K. Y. T.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. Tsang, K. Y.; Diaz, H.; Smith, A. B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947. Giannis, A.; Kolter, T. Angew. Chem., Int Ed. Engl. 1993, 32, 1244. Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Ernest, I.; J. Kalvoda, J.; Rihs, G.; Mutter, M. Tetrahedron Lett. 1990, 31, 4011. Kemp, D. S.; Bowen, B. R.; Muendal, C. C. J. Org. Chem. 1990, 55, 4650. Kemp, D. S.; Stites, W. E. Tetrahedron Lett. 1988, 29, 5057. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5077. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081 and references cited in these papers.
13. For examples of β-turn and β-sheet mimics see: Biagini, S. C. G.; North, M. Amino Acids, Peptides and Proteins: Specialist Periodical Reports Vol. 27; (Davies, J. S., Ed.; The Royal Society of Chemistry: London, 1996; Chapter 3. Peptide Secondary Structure Mimetics: Tetrahedron Symposia in Print Number 50; Kahn, M., Ed. Tetrahedron 1993, 49, 3433-3689. Horwell, D. C.; Naylor, D.; Willems, H. M. G. Bioorg. Med. Chem. Lett. 1997, 7, 31. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847. Kobayashi, K; Granja, J. R.; Ghaddidri, M. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 95. Tsang, K. Y. T.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. Tsang, K. Y.; Diaz, H.; Smith, A. B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947. Giannis, A.; Kolter, T. Angew. Chem., Int Ed. Engl. 1993, 32, 1244. Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Ernest, I.; J. Kalvoda, J.; Rihs, G.; Mutter, M. Tetrahedron Lett. 1990, 31, 4011. Kemp, D. S.; Bowen, B. R.; Muendal, C. C. J. Org. Chem. 1990, 55, 4650. Kemp, D. S.; Stites, W. E. Tetrahedron Lett. 1988, 29, 5057. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5077. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081 and references cited in these papers.
14. For examples of β-turn and β-sheet mimics see: Biagini, S. C. G.; North, M. Amino Acids, Peptides and Proteins: Specialist Periodical Reports Vol. 27; (Davies, J. S., Ed.; The Royal Society of Chemistry: London, 1996; Chapter 3. Peptide Secondary Structure Mimetics: Tetrahedron Symposia in Print Number 50; Kahn, M., Ed. Tetrahedron 1993, 49, 3433-3689. Horwell, D. C.; Naylor, D.; Willems, H. M. G. Bioorg. Med. Chem. Lett. 1997, 7, 31. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847. Kobayashi, K; Granja, J. R.; Ghaddidri, M. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 95. Tsang, K. Y. T.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. Tsang, K. Y.; Diaz, H.; Smith, A. B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947. Giannis, A.; Kolter, T. Angew. Chem., Int Ed. Engl. 1993, 32, 1244. Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Ernest, I.; J. Kalvoda, J.; Rihs, G.; Mutter, M. Tetrahedron Lett. 1990, 31, 4011. Kemp, D. S.; Bowen, B. R.; Muendal, C. C. J. Org. Chem. 1990, 55, 4650. Kemp, D. S.; Stites, W. E. Tetrahedron Lett. 1988, 29, 5057. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5077. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081 and references cited in these papers.
15. For examples of β-turn and β-sheet mimics see: Biagini, S. C. G.; North, M. Amino Acids, Peptides and Proteins: Specialist Periodical Reports Vol. 27; (Davies, J. S., Ed.; The Royal Society of Chemistry: London, 1996; Chapter 3. Peptide Secondary Structure Mimetics: Tetrahedron Symposia in Print Number 50; Kahn, M., Ed. Tetrahedron 1993, 49, 3433-3689. Horwell, D. C.; Naylor, D.; Willems, H. M. G. Bioorg. Med. Chem. Lett. 1997, 7, 31. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847. Kobayashi, K; Granja, J. R.; Ghaddidri, M. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 95. Tsang, K. Y. T.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. Tsang, K. Y.; Diaz, H.; Smith, A. B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947. Giannis, A.; Kolter, T. Angew. Chem., Int Ed. Engl. 1993, 32, 1244. Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Ernest, I.; J. Kalvoda, J.; Rihs, G.; Mutter, M. Tetrahedron Lett. 1990, 31, 4011. Kemp, D. S.; Bowen, B. R.; Muendal, C. C. J. Org. Chem. 1990, 55, 4650. Kemp, D. S.; Stites, W. E. Tetrahedron Lett. 1988, 29, 5057. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5077. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081 and references cited in these papers.
16. For examples of β-turn and β-sheet mimics see: Biagini, S. C. G.; North, M. Amino Acids, Peptides and Proteins: Specialist Periodical Reports Vol. 27; (Davies, J. S., Ed.; The Royal Society of Chemistry: London, 1996; Chapter 3. Peptide Secondary Structure Mimetics: Tetrahedron Symposia in Print Number 50; Kahn, M., Ed. Tetrahedron 1993, 49, 3433-3689. Horwell, D. C.; Naylor, D.; Willems, H. M. G. Bioorg. Med. Chem. Lett. 1997, 7, 31. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853. Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847. Kobayashi, K; Granja, J. R.; Ghaddidri, M. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 95. Tsang, K. Y. T.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. Tsang, K. Y.; Diaz, H.; Smith, A. B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947. Giannis, A.; Kolter, T. Angew. Chem., Int Ed. Engl. 1993, 32, 1244. Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Ernest, I.; J. Kalvoda, J.; Rihs, G.; Mutter, M. Tetrahedron Lett. 1990, 31, 4011. Kemp, D. S.; Bowen, B. R.; Muendal, C. C. J. Org. Chem. 1990, 55, 4650. Kemp, D. S.; Stites, W. E. Tetrahedron Lett. 1988, 29, 5057. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5077. Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081 and references cited in these papers.
17. Smith, C. K.; Regan, L. Acc. Chem. Res. 1997, 30, 153. Creighton, T. E. Proteins: Structures and Molecular Properties; Freeman: New York, 1993.
18. Smith, C. K.; Regan, L. Acc. Chem. Res. 1997, 30, 153. Creighton, T. E. Proteins: Structures and Molecular Properties; Freeman: New York, 1993.
19. For recent references see: Hanessian, S.; Yang, H. Tetrahedron Lett. 1997, 38, 3155. Seebach, D.; Gademann, K.; Schreiber, J. V.; Matthews, J. L.; Hintermann, T.; Jaun, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1997, 80, 2033. Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015. Daura, X.; vanGunsteren, W. F.; Rigo, D.; Juan, B.; Seebach, D. Chem. Eur. J. 1997, 3, 1410. Matthews, J. L.; Overhand, M.; Kuhnle, F. N. M.; Ciceri, P. E.; Seebach, D. Liebigs Annalen-Recueil 1997, 1371. Hintermann, T.; Seebach, D. Synlett 1997, 437. Hintermann, T.; Seebach, D. Chimia 1997, 51, 244. Seebach, D.; Matthews, J. L.; Meden, A.; Wessels, T.; Baerlocher, C.; McCusker, L. B. Helv. Chem. Acta 1997, 80, 173. Appella, D. H.; Christianson, L. A.; Klein, D. A. Powell, D. R.; Huang, X. L.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071. Lombardi, A.; Saviano, M.; Nastri, F.; Maglio, O.; Mazzeo, M.; Isernia, C.; Paolillo, L.; Pavone, V. Biopolymers 1996, 38, 693.
20. For recent references see: Hanessian, S.; Yang, H. Tetrahedron Lett. 1997, 38, 3155. Seebach, D.; Gademann, K.; Schreiber, J. V.; Matthews, J. L.; Hintermann, T.; Jaun, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1997, 80, 2033. Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015. Daura, X.; vanGunsteren, W. F.; Rigo, D.; Juan, B.; Seebach, D. Chem. Eur. J. 1997, 3, 1410. Matthews, J. L.; Overhand, M.; Kuhnle, F. N. M.; Ciceri, P. E.; Seebach, D. Liebigs Annalen-Recueil 1997, 1371. Hintermann, T.; Seebach, D. Synlett 1997, 437. Hintermann, T.; Seebach, D. Chimia 1997, 51, 244. Seebach, D.; Matthews, J. L.; Meden, A.; Wessels, T.; Baerlocher, C.; McCusker, L. B. Helv. Chem. Acta 1997, 80, 173. Appella, D. H.; Christianson, L. A.; Klein, D. A. Powell, D. R.; Huang, X. L.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071. Lombardi, A.; Saviano, M.; Nastri, F.; Maglio, O.; Mazzeo, M.; Isernia, C.; Paolillo, L.; Pavone, V. Biopolymers 1996, 38, 693.
21. For recent references see: Hanessian, S.; Yang, H. Tetrahedron Lett. 1997, 38, 3155. Seebach, D.; Gademann, K.; Schreiber, J. V.; Matthews, J. L.; Hintermann, T.; Jaun, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1997, 80, 2033. Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015. Daura, X.; vanGunsteren, W. F.; Rigo, D.; Juan, B.; Seebach, D. Chem. Eur. J. 1997, 3, 1410. Matthews, J. L.; Overhand, M.; Kuhnle, F. N. M.; Ciceri, P. E.; Seebach, D. Liebigs Annalen-Recueil 1997, 1371. Hintermann, T.; Seebach, D. Synlett 1997, 437. Hintermann, T.; Seebach, D. Chimia 1997, 51, 244. Seebach, D.; Matthews, J. L.; Meden, A.; Wessels, T.; Baerlocher, C.; McCusker, L. B. Helv. Chem. Acta 1997, 80, 173. Appella, D. H.; Christianson, L. A.; Klein, D. A. Powell, D. R.; Huang, X. L.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071. Lombardi, A.; Saviano, M.; Nastri, F.; Maglio, O.; Mazzeo, M.; Isernia, C.; Paolillo, L.; Pavone, V. Biopolymers 1996, 38, 693.
22. For recent references see: Hanessian, S.; Yang, H. Tetrahedron Lett. 1997, 38, 3155. Seebach, D.; Gademann, K.; Schreiber, J. V.; Matthews, J. L.; Hintermann, T.; Jaun, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1997, 80, 2033. Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015. Daura, X.; vanGunsteren, W. F.; Rigo, D.; Juan, B.; Seebach, D. Chem. Eur. J. 1997, 3, 1410. Matthews, J. L.; Overhand, M.; Kuhnle, F. N. M.; Ciceri, P. E.; Seebach, D. Liebigs Annalen-Recueil 1997, 1371. Hintermann, T.; Seebach, D. Synlett 1997, 437. Hintermann, T.; Seebach, D. Chimia 1997, 51, 244. Seebach, D.; Matthews, J. L.; Meden, A.; Wessels, T.; Baerlocher, C.; McCusker, L. B. Helv. Chem. Acta 1997, 80, 173. Appella, D. H.; Christianson, L. A.; Klein, D. A. Powell, D. R.; Huang, X. L.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071. Lombardi, A.; Saviano, M.; Nastri, F.; Maglio, O.; Mazzeo, M.; Isernia, C.; Paolillo, L.; Pavone, V. Biopolymers 1996, 38, 693.
23. For recent references see: Hanessian, S.; Yang, H. Tetrahedron Lett. 1997, 38, 3155. Seebach, D.; Gademann, K.; Schreiber, J. V.; Matthews, J. L.; Hintermann, T.; Jaun, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1997, 80, 2033. Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015. Daura, X.; vanGunsteren, W. F.; Rigo, D.; Juan, B.; Seebach, D. Chem. Eur. J. 1997, 3, 1410. Matthews, J. L.; Overhand, M.; Kuhnle, F. N. M.; Ciceri, P. E.; Seebach, D. Liebigs Annalen-Recueil 1997, 1371. Hintermann, T.; Seebach, D. Synlett 1997, 437. Hintermann, T.; Seebach, D. Chimia 1997, 51, 244. Seebach, D.; Matthews, J. L.; Meden, A.; Wessels, T.; Baerlocher, C.; McCusker, L. B. Helv. Chem. Acta 1997, 80, 173. Appella, D. H.; Christianson, L. A.; Klein, D. A. Powell, D. R.; Huang, X. L.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071. Lombardi, A.; Saviano, M.; Nastri, F.; Maglio, O.; Mazzeo, M.; Isernia, C.; Paolillo, L.; Pavone, V. Biopolymers 1996, 38, 693.
24. For recent references see: Hanessian, S.; Yang, H. Tetrahedron Lett. 1997, 38, 3155. Seebach, D.; Gademann, K.; Schreiber, J. V.; Matthews, J. L.; Hintermann, T.; Jaun, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1997, 80, 2033. Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015. Daura, X.; vanGunsteren, W. F.; Rigo, D.; Juan, B.; Seebach, D. Chem. Eur. J. 1997, 3, 1410. Matthews, J. L.; Overhand, M.; Kuhnle, F. N. M.; Ciceri, P. E.; Seebach, D. Liebigs Annalen-Recueil 1997, 1371. Hintermann, T.; Seebach, D. Synlett 1997, 437. Hintermann, T.; Seebach, D. Chimia 1997, 51, 244. Seebach, D.; Matthews, J. L.; Meden, A.; Wessels, T.; Baerlocher, C.; McCusker, L. B. Helv. Chem. Acta 1997, 80, 173. Appella, D. H.; Christianson, L. A.; Klein, D. A. Powell, D. R.; Huang, X. L.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071. Lombardi, A.; Saviano, M.; Nastri, F.; Maglio, O.; Mazzeo, M.; Isernia, C.; Paolillo, L.; Pavone, V. Biopolymers 1996, 38, 693.
25. For recent references see: Hanessian, S.; Yang, H. Tetrahedron Lett. 1997, 38, 3155. Seebach, D.; Gademann, K.; Schreiber, J. V.; Matthews, J. L.; Hintermann, T.; Jaun, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1997, 80, 2033. Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015. Daura, X.; vanGunsteren, W. F.; Rigo, D.; Juan, B.; Seebach, D. Chem. Eur. J. 1997, 3, 1410. Matthews, J. L.; Overhand, M.; Kuhnle, F. N. M.; Ciceri, P. E.; Seebach, D. Liebigs Annalen-Recueil 1997, 1371. Hintermann, T.; Seebach, D. Synlett 1997, 437. Hintermann, T.; Seebach, D. Chimia 1997, 51, 244. Seebach, D.; Matthews, J. L.; Meden, A.; Wessels, T.; Baerlocher, C.; McCusker, L. B. Helv. Chem. Acta 1997, 80, 173. Appella, D. H.; Christianson, L. A.; Klein, D. A. Powell, D. R.; Huang, X. L.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071. Lombardi, A.; Saviano, M.; Nastri, F.; Maglio, O.; Mazzeo, M.; Isernia, C.; Paolillo, L.; Pavone, V. Biopolymers 1996, 38, 693.
26. For recent references see: Hanessian, S.; Yang, H. Tetrahedron Lett. 1997, 38, 3155. Seebach, D.; Gademann, K.; Schreiber, J. V.; Matthews, J. L.; Hintermann, T.; Jaun, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1997, 80, 2033. Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015. Daura, X.; vanGunsteren, W. F.; Rigo, D.; Juan, B.; Seebach, D. Chem. Eur. J. 1997, 3, 1410. Matthews, J. L.; Overhand, M.; Kuhnle, F. N. M.; Ciceri, P. E.; Seebach, D. Liebigs Annalen-Recueil 1997, 1371. Hintermann, T.; Seebach, D. Synlett 1997, 437. Hintermann, T.; Seebach, D. Chimia 1997, 51, 244. Seebach, D.; Matthews, J. L.; Meden, A.; Wessels, T.; Baerlocher, C.; McCusker, L. B. Helv. Chem. Acta 1997, 80, 173. Appella, D. H.; Christianson, L. A.; Klein, D. A. Powell, D. R.; Huang, X. L.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071. Lombardi, A.; Saviano, M.; Nastri, F.; Maglio, O.; Mazzeo, M.; Isernia, C.; Paolillo, L.; Pavone, V. Biopolymers 1996, 38, 693.
27. For recent references see: Hanessian, S.; Yang, H. Tetrahedron Lett. 1997, 38, 3155. Seebach, D.; Gademann, K.; Schreiber, J. V.; Matthews, J. L.; Hintermann, T.; Jaun, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1997, 80, 2033. Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015. Daura, X.; vanGunsteren, W. F.; Rigo, D.; Juan, B.; Seebach, D. Chem. Eur. J. 1997, 3, 1410. Matthews, J. L.; Overhand, M.; Kuhnle, F. N. M.; Ciceri, P. E.; Seebach, D. Liebigs Annalen-Recueil 1997, 1371. Hintermann, T.; Seebach, D. Synlett 1997, 437. Hintermann, T.; Seebach, D. Chimia 1997, 51, 244. Seebach, D.; Matthews, J. L.; Meden, A.; Wessels, T.; Baerlocher, C.; McCusker, L. B. Helv. Chem. Acta 1997, 80, 173. Appella, D. H.; Christianson, L. A.; Klein, D. A. Powell, D. R.; Huang, X. L.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071. Lombardi, A.; Saviano, M.; Nastri, F.; Maglio, O.; Mazzeo, M.; Isernia, C.; Paolillo, L.; Pavone, V. Biopolymers 1996, 38, 693.
28. For recent references see: Hanessian, S.; Yang, H. Tetrahedron Lett. 1997, 38, 3155. Seebach, D.; Gademann, K.; Schreiber, J. V.; Matthews, J. L.; Hintermann, T.; Jaun, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1997, 80, 2033. Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015. Daura, X.; vanGunsteren, W. F.; Rigo, D.; Juan, B.; Seebach, D. Chem. Eur. J. 1997, 3, 1410. Matthews, J. L.; Overhand, M.; Kuhnle, F. N. M.; Ciceri, P. E.; Seebach, D. Liebigs Annalen-Recueil 1997, 1371. Hintermann, T.; Seebach, D. Synlett 1997, 437. Hintermann, T.; Seebach, D. Chimia 1997, 51, 244. Seebach, D.; Matthews, J. L.; Meden, A.; Wessels, T.; Baerlocher, C.; McCusker, L. B. Helv. Chem. Acta 1997, 80, 173. Appella, D. H.; Christianson, L. A.; Klein, D. A. Powell, D. R.; Huang, X. L.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071. Lombardi, A.; Saviano, M.; Nastri, F.; Maglio, O.; Mazzeo, M.; Isernia, C.; Paolillo, L.; Pavone, V. Biopolymers 1996, 38, 693.
29. For recent references see: Hanessian, S.; Yang, H. Tetrahedron Lett. 1997, 38, 3155. Seebach, D.; Gademann, K.; Schreiber, J. V.; Matthews, J. L.; Hintermann, T.; Jaun, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1997, 80, 2033. Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015. Daura, X.; vanGunsteren, W. F.; Rigo, D.; Juan, B.; Seebach, D. Chem. Eur. J. 1997, 3, 1410. Matthews, J. L.; Overhand, M.; Kuhnle, F. N. M.; Ciceri, P. E.; Seebach, D. Liebigs Annalen-Recueil 1997, 1371. Hintermann, T.; Seebach, D. Synlett 1997, 437. Hintermann, T.; Seebach, D. Chimia 1997, 51, 244. Seebach, D.; Matthews, J. L.; Meden, A.; Wessels, T.; Baerlocher, C.; McCusker, L. B. Helv. Chem. Acta 1997, 80, 173. Appella, D. H.; Christianson, L. A.; Klein, D. A. Powell, D. R.; Huang, X. L.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071. Lombardi, A.; Saviano, M.; Nastri, F.; Maglio, O.; Mazzeo, M.; Isernia, C.; Paolillo, L.; Pavone, V. Biopolymers 1996, 38, 693.
30. Ball, J. B.; Hughes, R. A.; Alewood, P. F.; Andrews, P. R. Tetrahedron 1993, 49, 3467. Rose, G. D.; Gierasch, L. M.; Smith, J. Adv. Protein Chem. 1985, 37, 1.
31. Ball, J. B.; Hughes, R. A.; Alewood, P. F.; Andrews, P. R. Tetrahedron 1993, 49, 3467. Rose, G. D.; Gierasch, L. M.; Smith, J. Adv. Protein Chem. 1985, 37, 1.
32. Synthetic Peptides A User's Guide; Grant, G. A.; Ed.; W. H. Freeman: New York, 1992; Chapter 2; Yao, J.; Fehrer, V. A.; Espejo, B. F.; Reymond, M. T.; Wright, P. E.; Dyson, H. J. J. Mol. Biol. 1994, 243, 736. Yao, J.; Bruschweiler, R.; Dyson, H. J.; Wright, P. E. J. Am. Chem. Soc. 1994, 116, 12051.
33. Synthetic Peptides A User's Guide; Grant, G. A.; Ed.; W. H. Freeman: New York, 1992; Chapter 2; Yao, J.; Fehrer, V. A.; Espejo, B. F.; Reymond, M. T.; Wright, P. E.; Dyson, H. J. J. Mol. Biol. 1994, 243, 736. Yao, J.; Bruschweiler, R.; Dyson, H. J.; Wright, P. E. J. Am. Chem. Soc. 1994, 116, 12051.
34. Synthetic Peptides A User's Guide; Grant, G. A.; Ed.; W. H. Freeman: New York, 1992; Chapter 2; Yao, J.; Fehrer, V. A.; Espejo, B. F.; Reymond, M. T.; Wright, P. E.; Dyson, H. J. J. Mol. Biol. 1994, 243, 736. Yao, J.; Bruschweiler, R.; Dyson, H. J.; Wright, P. E. J. Am. Chem. Soc. 1994, 116, 12051.
35. Richardson, J. S. Adv. Protein Chem. 1981, 34, 167.
36. Hayashi, T.; Asai, T.; Ogoshi, H. Tetrahedron Lett. 1997, 38, 3039. Chou, P. Y.; Fasman, G. D. J. Mol. Biol. 1997, 115, 135.
37. Hayashi, T.; Asai, T.; Ogoshi, H. Tetrahedron Lett. 1997, 38, 3039. Chou, P. Y.; Fasman, G. D. J. Mol. Biol. 1997, 115, 135.
38. For reviews on the assignment of peptide resonances and the determination of peptide conformation using NMR techniques see: Biomolecular NMR Spectroscopy; Evans, J. N. S.; Oxford University Press: Oxford, 1995; Chapter 4. Bystrov, V. F.; Portnova, S. L.; Balashova, T. A.; Koz'min, S. A.; Gavrilov, Yu. D.; Afanas'ev, V. A. Pure Appl. Chem. 1973, 36, 19. Dyson, H. J.; Wright, P. E. Annu. Rev. Biophys. Biophys. Chem. 1991, 20, 519. Ovchinnikov, Yu. A.; Ivanov, V. T. Tetrahedron 1975, 31, 2177; Deber, C. M. Madison, V.; Blout, E. R. Acc. Chem. Res. 1976, 9, 106.
39. For reviews on the assignment of peptide resonances and the determination of peptide conformation using NMR techniques see: Biomolecular NMR Spectroscopy; Evans, J. N. S.; Oxford University Press: Oxford, 1995; Chapter 4. Bystrov, V. F.; Portnova, S. L.; Balashova, T. A.; Koz'min, S. A.; Gavrilov, Yu. D.; Afanas'ev, V. A. Pure Appl. Chem. 1973, 36, 19. Dyson, H. J.; Wright, P. E. Annu. Rev. Biophys. Biophys. Chem. 1991, 20, 519. Ovchinnikov, Yu. A.; Ivanov, V. T. Tetrahedron 1975, 31, 2177; Deber, C. M. Madison, V.; Blout, E. R. Acc. Chem. Res. 1976, 9, 106.
40. For reviews on the assignment of peptide resonances and the determination of peptide conformation using NMR techniques see: Biomolecular NMR Spectroscopy; Evans, J. N. S.; Oxford University Press: Oxford, 1995; Chapter 4. Bystrov, V. F.; Portnova, S. L.; Balashova, T. A.; Koz'min, S. A.; Gavrilov, Yu. D.; Afanas'ev, V. A. Pure Appl. Chem. 1973, 36, 19. Dyson, H. J.; Wright, P. E. Annu. Rev. Biophys. Biophys. Chem. 1991, 20, 519. Ovchinnikov, Yu. A.; Ivanov, V. T. Tetrahedron 1975, 31, 2177; Deber, C. M. Madison, V.; Blout, E. R. Acc. Chem. Res. 1976, 9, 106.
41. For reviews on the assignment of peptide resonances and the determination of peptide conformation using NMR techniques see: Biomolecular NMR Spectroscopy; Evans, J. N. S.; Oxford University Press: Oxford, 1995; Chapter 4. Bystrov, V. F.; Portnova, S. L.; Balashova, T. A.; Koz'min, S. A.; Gavrilov, Yu. D.; Afanas'ev, V. A. Pure Appl. Chem. 1973, 36, 19. Dyson, H. J.; Wright, P. E. Annu. Rev. Biophys. Biophys. Chem. 1991, 20, 519. Ovchinnikov, Yu. A.; Ivanov, V. T. Tetrahedron 1975, 31, 2177; Deber, C. M. Madison, V.; Blout, E. R. Acc. Chem. Res. 1976, 9, 106.
42. For reviews on the assignment of peptide resonances and the determination of peptide conformation using NMR techniques see: Biomolecular NMR Spectroscopy; Evans, J. N. S.; Oxford University Press: Oxford, 1995; Chapter 4. Bystrov, V. F.; Portnova, S. L.; Balashova, T. A.; Koz'min, S. A.; Gavrilov, Yu. D.; Afanas'ev, V. A. Pure Appl. Chem. 1973, 36, 19. Dyson, H. J.; Wright, P. E. Annu. Rev. Biophys. Biophys. Chem. 1991, 20, 519. Ovchinnikov, Yu. A.; Ivanov, V. T. Tetrahedron 1975, 31, 2177; Deber, C. M. Madison, V.; Blout, E. R. Acc. Chem. Res. 1976, 9, 106.
43. For examples on the use of amide hydrogen temperature coefficients to obtain conformational information in peptides see: Bönzli, P.; Gerig, J. T. J. Am. Chem. Soc. 1990, 112, 3720; Kessler, H.; Will, M.; Antel, J.; Beck, H.; Sheldrick, G. M. Helv. Chim. Acta 1989, 72, 530; Inman, W.; Crews, P. J. Am. Chem. Soc., 1989, 111, 2822. Kessler, H.; Bats, J. W.; Lautz, J.; Müller, A. Liebigs Ann. Chem. 1983, 913. Di Blasio, B.; Rossi, F.; Benedetti, E.; Pavone, V.; Pedone, C.; Temussi, P. A.; Zanotti, G.; Tancredi, T. J. Am. Chem. Soc. 1989, 111, 9089.
44. For examples on the use of amide hydrogen temperature coefficients to obtain conformational information in peptides see: Bönzli, P.; Gerig, J. T. J. Am. Chem. Soc. 1990, 112, 3720; Kessler, H.; Will, M.; Antel, J.; Beck, H.; Sheldrick, G. M. Helv. Chim. Acta 1989, 72, 530; Inman, W.; Crews, P. J. Am. Chem. Soc., 1989, 111, 2822. Kessler, H.; Bats, J. W.; Lautz, J.; Müller, A. Liebigs Ann. Chem. 1983, 913. Di Blasio, B.; Rossi, F.; Benedetti, E.; Pavone, V.; Pedone, C.; Temussi, P. A.; Zanotti, G.; Tancredi, T. J. Am. Chem. Soc. 1989, 111, 9089.
45. For examples on the use of amide hydrogen temperature coefficients to obtain conformational information in peptides see: Bönzli, P.; Gerig, J. T. J. Am. Chem. Soc. 1990, 112, 3720; Kessler, H.; Will, M.; Antel, J.; Beck, H.; Sheldrick, G. M. Helv. Chim. Acta 1989, 72, 530; Inman, W.; Crews, P. J. Am. Chem. Soc., 1989, 111, 2822. Kessler, H.; Bats, J. W.; Lautz, J.; Müller, A. Liebigs Ann. Chem. 1983, 913. Di Blasio, B.; Rossi, F.; Benedetti, E.; Pavone, V.; Pedone, C.; Temussi, P. A.; Zanotti, G.; Tancredi, T. J. Am. Chem. Soc. 1989, 111, 9089.
46. For examples on the use of amide hydrogen temperature coefficients to obtain conformational information in peptides see: Bönzli, P.; Gerig, J. T. J. Am. Chem. Soc. 1990, 112, 3720; Kessler, H.; Will, M.; Antel, J.; Beck, H.; Sheldrick, G. M. Helv. Chim. Acta 1989, 72, 530; Inman, W.; Crews, P. J. Am. Chem. Soc., 1989, 111, 2822. Kessler, H.; Bats, J. W.; Lautz, J.; Müller, A. Liebigs Ann. Chem. 1983, 913. Di Blasio, B.; Rossi, F.; Benedetti, E.; Pavone, V.; Pedone, C.; Temussi, P. A.; Zanotti, G.; Tancredi, T. J. Am. Chem. Soc. 1989, 111, 9089.
47. For examples on the use of amide hydrogen temperature coefficients to obtain conformational information in peptides see: Bönzli, P.; Gerig, J. T. J. Am. Chem. Soc. 1990, 112, 3720; Kessler, H.; Will, M.; Antel, J.; Beck, H.; Sheldrick, G. M. Helv. Chim. Acta 1989, 72, 530; Inman, W.; Crews, P. J. Am. Chem. Soc., 1989, 111, 2822. Kessler, H.; Bats, J. W.; Lautz, J.; Müller, A. Liebigs Ann. Chem. 1983, 913. Di Blasio, B.; Rossi, F.; Benedetti, E.; Pavone, V.; Pedone, C.; Temussi, P. A.; Zanotti, G.; Tancredi, T. J. Am. Chem. Soc. 1989, 111, 9089.
48. Gellman, S. H.; Dado, G. P.; Liang, G.-B.; Adams, B. R. J. Am. Chem. Soc. 1991, 113, 1164. Stevens, E. S.; Sugawara, N.; Bonora, G. M.; Toniolo, C. J. Am. Chem. Soc. 1980, 102, 7048.
49. Gellman, S. H.; Dado, G. P.; Liang, G.-B.; Adams, B. R. J. Am. Chem. Soc. 1991, 113, 1164. Stevens, E. S.; Sugawara, N.; Bonora, G. M.; Toniolo, C. J. Am. Chem. Soc. 1980, 102, 7048.
50. Woody, R. W. In The Peptides: Analysis, Synthesis, Biology: Volume 7 Conformation in Biology and Drug Design; Udenfriend, S.; Meienhofer, J.; Hruby, V. J., Eds.; Academic Press: London 1985; Chapter 2.
51. Larive, C. K.; Guerra, L.; Rabenstein, D. L. J. Am. Chem. Soc., 1992, 114, 7331. Kessler, H.; Mronga, S.; Will, M.; Schmidt, U. Helv. Chim. Acta 1990, 73, 25.
52. Larive, C. K.; Guerra, L.; Rabenstein, D. L. J. Am. Chem. Soc., 1992, 114, 7331. Kessler, H.; Mronga, S.; Will, M.; Schmidt, U. Helv. Chim. Acta 1990, 73, 25.
53. Kopple, K. D.; Wiley, G. R.; Tauke, R. Biopolymers 1973, 12, 627. Barfield, M.; Gearhart, H. L. J. Am. Chem. Soc. 1973, 95, 641. Pardi, A.; Billeter, M.; Wüthrich, K. J. Mol. Biol. 1984, 180, 741. Ramachandran, G. N. Chandrasekaran, R.; Kopple, K. D. Biopolymers 1971, 10, 2113. Wuthrich, K. NMR of Proteins and Nucleic Acids; Wiley: New York, 1986.
54. Kopple, K. D.; Wiley, G. R.; Tauke, R. Biopolymers 1973, 12, 627. Barfield, M.; Gearhart, H. L. J. Am. Chem. Soc. 1973, 95, 641. Pardi, A.; Billeter, M.; Wüthrich, K. J. Mol. Biol. 1984, 180, 741. Ramachandran, G. N. Chandrasekaran, R.; Kopple, K. D. Biopolymers 1971, 10, 2113. Wuthrich, K. NMR of Proteins and Nucleic Acids; Wiley: New York, 1986.
55. Kopple, K. D.; Wiley, G. R.; Tauke, R. Biopolymers 1973, 12, 627. Barfield, M.; Gearhart, H. L. J. Am. Chem. Soc. 1973, 95, 641. Pardi, A.; Billeter, M.; Wüthrich, K. J. Mol. Biol. 1984, 180, 741. Ramachandran, G. N. Chandrasekaran, R.; Kopple, K. D. Biopolymers 1971, 10, 2113. Wuthrich, K. NMR of Proteins and Nucleic Acids; Wiley: New York, 1986.
56. Kopple, K. D.; Wiley, G. R.; Tauke, R. Biopolymers 1973, 12, 627. Barfield, M.; Gearhart, H. L. J. Am. Chem. Soc. 1973, 95, 641. Pardi, A.; Billeter, M.; Wüthrich, K. J. Mol. Biol. 1984, 180, 741. Ramachandran, G. N. Chandrasekaran, R.; Kopple, K. D. Biopolymers 1971, 10, 2113. Wuthrich, K. NMR of Proteins and Nucleic Acids; Wiley: New York, 1986.
57. Kopple, K. D.; Wiley, G. R.; Tauke, R. Biopolymers 1973, 12, 627. Barfield, M.; Gearhart, H. L. J. Am. Chem. Soc. 1973, 95, 641. Pardi, A.; Billeter, M.; Wüthrich, K. J. Mol. Biol. 1984, 180, 741. Ramachandran, G. N. Chandrasekaran, R.; Kopple, K. D. Biopolymers 1971, 10, 2113. Wuthrich, K. NMR of Proteins and Nucleic Acids; Wiley: New York, 1986.
58. For other examples of antiparallel β-sheet formation in peptides see: Kawano, K.; Yoneya, T.; Miyata, T.; Yoshikawa, K.; Tokunga, F.; Terada, Y.; Iwanaga, S. J. Biol. Chem. 1990, 265, 15365. Blanco, F. J.; Jimenez, M. A.; Herranz, J.; Rico M.; Santoro, J.; Nieto, J. L. J. Am. Chem. Soc. 1993, 115, 5887. Sieber, V.; Moe, G. R. Biochemistry 1996, 35, 181.
59. For other examples of antiparallel β-sheet formation in peptides see: Kawano, K.; Yoneya, T.; Miyata, T.; Yoshikawa, K.; Tokunga, F.; Terada, Y.; Iwanaga, S. J. Biol. Chem. 1990, 265, 15365. Blanco, F. J.; Jimenez, M. A.; Herranz, J.; Rico M.; Santoro, J.; Nieto, J. L. J. Am. Chem. Soc. 1993, 115, 5887. Sieber, V.; Moe, G. R. Biochemistry 1996, 35, 181.
60. For other examples of antiparallel β-sheet formation in peptides see: Kawano, K.; Yoneya, T.; Miyata, T.; Yoshikawa, K.; Tokunga, F.; Terada, Y.; Iwanaga, S. J. Biol. Chem. 1990, 265, 15365. Blanco, F. J.; Jimenez, M. A.; Herranz, J.; Rico M.; Santoro, J.; Nieto, J. L. J. Am. Chem. Soc. 1993, 115, 5887. Sieber, V.; Moe, G. R. Biochemistry 1996, 35, 181.
61. Sibanda, B. L.; Thornton, J. M. J. Mol. Biol. 1993, 229, 428.
62. Chou, P. Y.; Fasman, G. D. Annu. Rev. Biochem. 1978, 47, 251. Wilmot, C. M.; Thornton, J. M. J. Mol. Biol. 1988, 203, 221.
63. Chou, P. Y.; Fasman, G. D. Annu. Rev. Biochem. 1978, 47, 251. Wilmot, C. M.; Thornton, J. M. J. Mol. Biol. 1988, 203, 221.
64. Allen, M. C.; Brandish, D. E.; Fullerton, J. D.; Wade, R. J. Chem. Soc., Perkin Trans. 1 1986, 989; Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1990, 1745.
65. Allen, M. C.; Brandish, D. E.; Fullerton, J. D.; Wade, R. J. Chem. Soc., Perkin Trans. 1 1986, 989; Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans. 2 1990, 1745.
66. Weiland, T.; Birr, C.; Burgermeister, W.; Trietsch, P.; Rohr, G. Justus Liebigs Ann. Chem., 1974, 24.
67. Krois, D.; Lehner, H. J. Chem. Soc., Perkin Trans, 2 1990, 1745.