Pleated sheets and turns of β-peptides with proteinogenic side chains

Angewandte Chemie - International Edition

Volumn 38, Issue 11, 1999, Pages 1595-1597

  Seebach, Dieter ^a   Abele, Stefan ^a   Gademann, Karl ^a   Jaun, Bernhard ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Amino acids; NMR spectroscopy; Peptides; Peptidomimetics

Indexed keywords

AMINO ACID; PEPTIDE;

AMINO ACID SEQUENCE; ARTICLE; CRYSTAL STRUCTURE; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN CONFORMATION; PROTEIN SECONDARY STRUCTURE; PROTEIN STRUCTURE;

EID: 0033153367     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990601)38:11<1595::AID-ANIE1595>3.0.CO;2-0     Document Type: Article

References (28)

1. C. Branden, J. Tooze, Introduction to Protein Structure, 2nd ed., Garland, New York, 1998: Y. Duan, P. A. Kollman, Science 1998, 282, 740-744; H. J. C. Berendsen, Science 1998, 282, 642-643.
2. C. Branden, J. Tooze, Introduction to Protein Structure, 2nd ed., Garland, New York, 1998: Y. Duan, P. A. Kollman, Science 1998, 282, 740-744; H. J. C. Berendsen, Science 1998, 282, 642-643.
3. C. Branden, J. Tooze, Introduction to Protein Structure, 2nd ed., Garland, New York, 1998: Y. Duan, P. A. Kollman, Science 1998, 282, 740-744; H. J. C. Berendsen, Science 1998, 282, 642-643.
4. a) D. Seebach, M. Overhand, F. N. M. Kühnle, B. Martinoni, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1996, 79, 913-941;
5. b) review: D. Seebach, J. L. Matthews, Chem. Commun. 1997, 21, 2015-2022; S. H. Gellman, Acc. Chem. Res. 1998, 31, 173-180.
6. b) review: D. Seebach, J. L. Matthews, Chem. Commun. 1997, 21, 2015-2022; S. H. Gellman, Acc. Chem. Res. 1998, 31, 173-180.
7. D. Seebach, S. Abele, K. Gademann, G. Guichard, T. Hintermann, B. Jaun, J. L. Matthews, J. V. Schreiber, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1998, 81, 932-982.
8. X. Daura, K. Gademann, B. Jaun, D. Seebach, W. F. van Gunsteren, A. E. Mark, Angew. Chem. 1999, 111, 249-253; Angew. Chem. Int. Ed. 1999, 38, 236-240.
9. X. Daura, K. Gademann, B. Jaun, D. Seebach, W. F. van Gunsteren, A. E. Mark, Angew. Chem. 1999, 111, 249-253; Angew. Chem. Int. Ed. 1999, 38, 236-240.
10. The superscripted number after β specifies the position of the side chain on the corresponding β-amino acid; see T. Hintermann, D. Seebach, Synlett 1997, 437-438.
11. T. Hintermann, D. Seebach, Chimia 1997, 51, 244-247.
12. D. Seebach, K. Gademann, J. V. Schreiber, J. L. Matthews, T. Hintermann, B. Jaun, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1997, 80, 2033-2038.
13. D. Seebach, S. Abele, T. Sifferlen, M. Hänggi, S. Gruner, P. Seiler, Helv. Chim. Acta 1998, 81, 2218-2243.
14. G. Guichard, D. Seebach, Chimia 1997, 51, 315-318; G. Guichard, S. Abele, D. Seebach, Helv. Chim. Acta 1998, 81, 187-206; S. Abele, G. Guichard, D. Seebach, Helv. Chim. Acta 1998, 81, 2141-2156.
15. G. Guichard, D. Seebach, Chimia 1997, 51, 315-318; G. Guichard, S. Abele, D. Seebach, Helv. Chim. Acta 1998, 81, 187-206; S. Abele, G. Guichard, D. Seebach, Helv. Chim. Acta 1998, 81, 2141-2156.
16. G. Guichard, D. Seebach, Chimia 1997, 51, 315-318; G. Guichard, S. Abele, D. Seebach, Helv. Chim. Acta 1998, 81, 187-206; S. Abele, G. Guichard, D. Seebach, Helv. Chim. Acta 1998, 81, 2141-2156.
17. 2-HLeu-OH of type II (Figure 1 a) also shows very poor solubility.
18. 2) = 0.105 for 392 variables and 2409 reflections with 1 > 2σ(1). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-113798. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
19. 2) = 0.105 for 392 variables and 2409 reflections with 1 > 2σ(1). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-113798. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
20. D. Seebach, J. L. Matthews, A. Meden, T. Wessels, C. Baerlocher, L. B. McCusker, Helv. Chim. Acta 1997, 80, 173-182.
21. [3] an indication that this Cotton effect may be produced mainly by the ten-membered hydrogen-bonded ring.
22. R. Koradi, M. Billeter, K. Wüthrich, J. Mol. Graphics 1996, 14, 51-54.
23. 2-HPro-: S. Krauthäuser, L. A. Christianson, D. R. Powell, S. H. Gellman, J. Am. Chem. Soc. 1997, 119, 11719-11720; Y. J. Chung, L. A. Christianson, H. E. Stanger, D. R. Powell, S. H. Gellman, J. Am. Chem. Soc. 1998, 120, 10555-10556.
24. 2-HPro-: S. Krauthäuser, L. A. Christianson, D. R. Powell, S. H. Gellman, J. Am. Chem. Soc. 1997, 119, 11719-11720; Y. J. Chung, L. A. Christianson, H. E. Stanger, D. R. Powell, S. H. Gellman, J. Am. Chem. Soc. 1998, 120, 10555-10556.
25. First example of a pharmacologically active β-peptide with affinity for a human receptor: K. Gademann, M. Ernst, D. Hoyer, D. Seebach, Angew. Chem. 1999, 111, 1302-1304; Angew. Chem. Int. Ed. 1999, 38, 1223-1226.
26. First example of a pharmacologically active β-peptide with affinity for a human receptor: K. Gademann, M. Ernst, D. Hoyer, D. Seebach, Angew. Chem. 1999, 111, 1302-1304; Angew. Chem. Int. Ed. 1999, 38, 1223-1226.
27. K. Gademann, B. Jaun, D. Seebach, R. Perozzo, L. Scapozza, G. Folkers, Helv. Chim. Acta 1999, 82, 1.
28. D. Seebach, S. Abele, J. V. Schreiber, B. Martinoni, A. K. Nussbaum, H. Schild, H. Schulz, H. Hennecke, R. Wössner, F. Bitsch, Chimia 1998, 52, 734-739.