Conformation Design of a Fully Flexible βII-Hairpin Analogue

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 16, 1997, Pages 1745-1747

  Schopfer, Ulrich ^a   Stahl, Martin ^a   Brandl, Trixi ^a   Hoffmann, Reinhard W ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Conformation analysis; Hydrogen bonds; Peptido mimetics

Indexed keywords

EID: 0030824028     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199717451     Document Type: Article

References (17)

1. a) R. Hirschmann, Angew. Chem. 1991, 103, 1305-1330; Angew. Chem. Int. Ed. Engl. 1991, 30, 1278-1301;
2. a) R. Hirschmann, Angew. Chem. 1991, 103, 1305-1330; Angew. Chem. Int. Ed. Engl. 1991, 30, 1278-1301;
3. b) G. Müller, ibid. 1996, 108, 2941-2943 and 1996, 35, 2767-2769.
4. b) G. Müller, ibid. 1996, 108, 2941-2943 and 1996, 35, 2767-2769.
5. a) J. P. Schneider, J. W. Kelly, Chem. Rev. 1995, 95, 2169-2187;
6. b) M. Kahn, Synlett 1993, 821-826.
7. T. S. Haque, J. C. Little, S. H. Gellman, J. Am. Chem. Soc. 1994, 116, 4105-4106, and references therein.
8. R. W. Hoffmann, Angew. Chem. 1992, 104, 1147-1157; Angew. Chem. Int. Ed. Engl. 1992, 31, 1124-1134.
9. R. W. Hoffmann, Angew. Chem. 1992, 104, 1147-1157; Angew. Chem. Int. Ed. Engl. 1992, 31, 1124-1134.
10. J. B. Ball, R. A. Hughes, P. F. Alewood, P. R. Andrews, Tetrahedron 1993, 49, 3467-3478.
11. Macromodel 4.5, Department of Chemistry, Columbia University, New York, NY 10027 (USA).
12. J. C. Anderson, S. V. Ley, S. P. Marsden, Tetrahedron Lett. 1994, 35, 2087-2090.
13. For the interpretation of IR and NMR data, see for example a) S. H. Gellman, G. P. Dado, G.-B. Liang, B. R. Adams, J. Am. Chem. Soc. 1991, 113, 1164-1173; b) G.-B. Liang, J M. Desper, S. H. Gellman, ibid. 1993, 115, 925-938.
14. For the interpretation of IR and NMR data, see for example a) S. H. Gellman, G. P. Dado, G.-B. Liang, B. R. Adams, J. Am. Chem. Soc. 1991, 113, 1164-1173; b) G.-B. Liang, J M. Desper, S. H. Gellman, ibid. 1993, 115, 925-938.
15. R. Göttlich, B. C. Kahrs, J. Krüger, R. W. Hoffmann, Chem. Common. 1997, 247-251.
16. R. R. Gardner, G.-B. Liang, S. H. Gellman, J. Am. Chem. Soc. 1995, 117, 3280-3281.
17. With two methyl substituents at the double bond of 6, a conformation corresponding to a β turn can be induced due to 1,3-allylic strain[10].