Studies on the conformation of boc-protected (S)-(+)-isovaline homopeptide methyl esters in the solid state and in solution

Liebigs Annales

Volumn , Issue 8, 1997, Pages 1697-1710

  Jaun, Bernhard ^a   Tanaka, Masakazu ^a   Seiler, Paul ^a   Kühnle, Florian N M ^a   Braun, Christine ^a   Seebach, Dieter ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Circular dichroism; Helical structures; Peptides

Indexed keywords

EID: 33748728148     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970811     Document Type: Article

References (43)

1. S. Rebuffat, M. E. Hajji, P. Hennig, D. Davoust, B. Bodo, Int. J. Pept. Protein Res. 1989, 34, 200-210.
2. S. Rebuffat, Y. Prigent, C. Auvin-Guette, B. Bodo, Eur. J. Biochem. 1991, 201, 661-674.
3. I. L. Karle, P. Balaram, Biochemistry 1990, 29, 6747-6756.
4. G. L. Millhauser, Biochemistry 1995, 34, 3873-3877.
5. C. Toniolo, M. Crisma, F. Formaggio, G. Valle, G. Cavicchioni, G. Précigoux, A. Aubry, J. Kamphuis, Biopolymers 1993, 33, 1061-1072.
6. E. Benedetti, C. Toniolo, P. Hardy, V. Barone, A. Bavoso, B. Di Blasio, P. Grimaldi, F. Lelj, V. Pavone, C. Pedone, G. M. Bonora, I. Lingham, J. Am. Chem. Soc. 1984, 106, 8146-8152.
7. G. Valle, M. Crisma, C. Toniolo, R. Beisswenger, A. Rieker, G. Jung, Liebigs Ann. Chem. 1989, 337-343.
8. M. Crisma, G. Valle, M. Pantano, F. Formaggio, G. M. Bonora, C. Toniolo, J. Kamphuis, Recl. Trav. Chim. Pays-Bas 1995, 114, 325-331.
9. M. Crisma, F. Formaggio, M. Pantano, G. Valle, G. M. Bonora, C. Toniolo, H. E. Schoemaker, J. Kamphuis, J. Chem. Soc., Perkin Trans. 2 1994, 1735-1742.
10. F. Formaggio, M. Crisma, G. M. Bonora, M. Pantano, G. Valle, C. Toniolo, A. Aubry, D. Bayeul, J. Kamphuis, Pept. Res. 1995, 8, 6-15.
11. G. Valle, M. Crisma, C. Toniolo, R. Beisswenger, A. Rieker, G. Jung, J. Am. Chem. Soc. 1989, 111, 6828-6833.
12. R. Fitzi, D. Seebach, Tetrahedron 1988, 44, 5277-5292.
13. For an extensive review on this subject, see D. Seebach, A. R. Sting, M. Hoffmann, Angew. Chem. 1996, 108, 2880-2921;
14. Angew. Chem. Int. Ed. Engl. 1996, 35, 2708-2748.
15. D. Seebach, E. Dziadulewicz, L. Behrendt, S. Cantoreggi, R. Fitzi, Liebigs Ann. Chem. 1989, 1215-1232.
16. D. Seebach, T. Gees, F. Schuler, Liebigs Ann. Chem. 1993, 785-799; Erratum: ibid 1994, 529.
17. A. Studer, D. Seebach, Liebigs Ann. 1995, 217-222.
18. C. Toniolo, E. Benedetti, TIBS 1991, 16, 350-353.
19. E. Benedetti, B. Di Blasio, V. Pavone, C. Pedone, A. Santini, M. Crisma, C. Toniolo in Molecular Conformation and Biological Interactions, (Eds. P. Balaram, S. Ramaseshan), Indian Academy of Sciences, Bangalore, 1991, pp. 497-502.
20. S. Macura, R. R. Ernst, Mol. Phys. 1980, 41, 95-117.
21. K. Wüthrich, NMR of Proteins and Nucleic Acids, Wiley, New York, 1986, pp. 162-166.
22. M. Pantano, F. Formaggio, M. Crisma, G. M. Bonora, C. Toniolo, A. Aubry, D. Bayeul, A. Dautant, G. Précigoux, W. H. J. Boesten, H. E. Schoemaker, J. Kamphuis, Pept. Res. 1993, 6, 196-204.
23. F. Formaggio, S. Pegoraro, M. Crisma, G. Valle, C. Toniolo, G. Précigoux, W. H. J. Boesten, H. E. Schoemaker, J. Kamphuis, J. Biomol. Struct. & Dynam. 1993, 10, 919-931.
24. 6]DMSO (v/v).
25. J. D. Dunitz, X-Ray Analysis and the Structure of Organic Molecules, 2nd ed., Verlag Helvetica Chimica Acta, Basel, 1995.
26. "Structure Correlation" (Eds. H.-B. Bürgi, J. D. Dunitz), VCH, Weinheim, 1994.
27. T. S. Sudha, E. K. S. Vijayakumar, P. Balaram, Int. J. Peptide Protein Res. 1983, 22, 464-468.
28. C. Toniolo, F. Formaggio, M. Crisma, H. E. Schoemaker, J. Kamphuis, Tetrahedron: Asymm. 1994, 5, 507-510.
29. G. Yoder, T. A. Keiderling, F. Formaggio, M. Crisma, C. Toniolo, J. Kamphuis, Tetrahedron: Asymmetry 1995, 6, 687-690.
30. F. Formaggio, M. Crisma, C. Toniolo, J. Kamphuis, Biopolymers 1996, 38, 301-304.
31. C. Toniolo, A. Polese, F. Formaggio, M. Crisma, J. Kamphuis, J. Am. Chem. Soc. 1996, 118, 2744-2745.
32. M. Pantano, F. Formaggio, M. Crisma, G. M. Bonora, S. Mammi, E. Peggion, C. Toniolo, W. H. J. Boesten, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Macromolecules 1993, 26, 1980-1984.
33. D-(αMe)Phe-peptides show a very strong preference for right-handed helical conformations and only one of the compounds investigated in this series adopts a different helical conformation in the crystalline state.
34. G. Valle, M. Pantano, F. Formaggio, M. Crisma, C. Toniolo, G. Précigoux, G. Sulzenbacher, W. H. J. Boesten, Q. B. Broxterman, H. E. Schoemaker, J. Kamphuis, Biopolymers 1993, 33, 1617-1625.
35. J. M. Scholtz, S. Marqusee, R. L. Baldwin, E. J. York, J. M. Stewart, M. Santoro, D. W. Bolen, Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 2854-2858.
36. T. Ooi, M. Oobatake, Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 2859-2863.
37. J. M. Scholtz, R. L. Baldwin in Peptides: Synthesis, Structures, and Applications, (Ed. B. Gutte), Academic Press, San Diego, 1995, pp. 171-192.
38. G. R. Marshall, D. D. Beusen, G. V. Nikiforovich in Peptides: Synthesis, Structures, and Applications, (Ed. B. Gutte), Academic Press, San Diego, 1995, pp. 193-245.
39. R.-P. Hummel, C. Toniolo, G. Jung, Angew. Chem. 1987, 99, 1180-1182;
40. Angew. Chem. Int. Ed. Engl. 1987, 26, 1150-1152.
41. K. Nebel, M. Mutter, Tetrahedron 1988, 44, 4793-4796.
42. G. R. Marshall, J. D. Clark, J. B. Dunbar Jr., G. D. Smith, J. Zabrocki, A. S. Redlinski, M. T. Leplawy, Int. J. Pept. Protein Res. 1988, 32, 544-555.
43. Further details of the crystal structures are available on request from CCDC upon quoting the depository number 100311, the author names and the journal citation.