112. Synthesis, conformational properties, and synthetic applications of novel optically pure α,α-disubstituted (R)- and (S)-glycines ('α-chimeras') combining side chains of Asp, Glu, Leu, Phe, Ser, and Val

Helvetica Chimica Acta

Volumn 79, Issue 5, 1996, Pages 1315-1337

  Obrecht, Daniel ^a   Abrecht, Christine ^a   Altorfer, Michael ^a   Bohdal, Udo ^a   Grieder, Alfred ^a   Kleber, Martina ^a   Pfyffer, Patrick ^a   Müller, Klaus ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ASPARTIC ACID DERIVATIVE; GLYCINE DERIVATIVE; SERINE DERIVATIVE;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; DRUG STRUCTURE; DRUG SYNTHESIS; PROTEIN STRUCTURE; PROTEIN SYNTHESIS;

EID: 0030058482     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.19960790508     Document Type: Article

References (38)

1. G. L. Olson, M. E. Voss, D. E. Hill, M. Kahn, V. S. Madison, C. M. Cook, J Am. Chem. Soc. 1990, 112, 323.
2. V. J. Hrubi, F. A. Obeidi, W. Kazmiersky, Biochem. J. 1990, 268, 249.
3. T. Masquelin, E. Broger, K. Müller, R. Schmid, D. Obrecht, Helv. Chim. Acta 1994, 77, 1395.
4. B. Di Blasio, V. Pavone, A. Lombardi, C Pedone, E. Benedetti, Biopolymers 1993, 33, 1037.
5. I. L. Karle, P. Balaram, Biochemistry 1990, 29, 6747.
6. P. Wipf, H. Heimgartner, Helv. Chim. Acta 1988, 71, 258
7. D. Obrecht, O. Bohdal, C. Lehmann, P. Schönholzer, K. Müller, Tetrahedron 1995, 51, 10883.
8. D. Obrecht, C. Lehmann, R. Ruffieux, P. Schönholzer, K. Müller, Helv. Chim. Acta 1995, 78, 1567.
9. D Obrecht, H. Karajiannis, C. Lehmann, P. Schönholzer, C. Spiegler, K. Müller, Helv. Chim. Acta 1995, 78, 703.
10. D. Obrecht, U. Bohdal, C. Broger, D. Bur, C. Lehmann, R. Ruffieux, P. Schönholzer, C. Spiegler, K. Müller, Helv. Chim. Acta 1995, 78, 563.
11. D. Obrecht, C. Spiegler, P Schönholzer, K. Müller, H. Heimgartner, F Stierli, Helv. Chim. Acta 1992, 75, 1666.
12. M. Mutter, Angew. Chem. 1985, 97, 639.
13. C. Toniolo, CRC Critical Rev. Biochem. 1980, 9, 1.
14. B. V. V. Prasad, P. Balaram, CRC Critical Rev. Biochem. 1984, 16, 307.
15. C. E. Spiegler, 'Synthesis and Conformation Studies of Peptides Containing Novel α,α-Disubstituted Amino Acids', Ph.D. Thesis, 1993, University of Zürich.
16. E. Benedetti, C. Toniolo, P. Hardy, V. Barone, B. Bavoso, B. Di Blasio, P. Grimaldi, F. Lelj, V. Pavone, C. Pedone, G. M Bonora, I. Lingham, J. Am. Chem. Soc. 1984, 106, 8146.
17. G. M. Bonora, C. Toniolo, B. Di Blasio, V. Pavone, C. Pedone, E. Benedetti, I. Lingham, P. G. M. Hardy, J. Am. Chem. Soc. 1984, 106, 8152.
18. V. Barone, F. Lelj, A Bavoso, B. Di Blasio, P. Grimaldi, V. Pavone, C. Pedone, Biopolymers 1985, 24, 1759.
19. M. Crisma, G. Valle, G. M. Bonora, C Toniolo, F. Lelj, V. Barone, F. Fraternali, P. M. Hardy, H. L. S. M. Maia, Biopolymers 1991, 31, 637.
20. C. Toniolo, E. Benedetti, ISI Atlas Sci.. Biochem. 1988, 255.
21. D. Obrecht, M. Altorfer, C. Lehmann, P. Schönholzer, K. Müller, J. Org. Chem. 1996, to be published.
22. D. Obrecht, U. Bohdal, R. Ruffieux, K. Müller, Helv. Chim. Acta 1994, 77, 1423.
23. M. Altorfer, 'Templates for the Position-Independent Nucleation of α-Helices in Peptides', Ph.D. Thesis, 1996, University of Zürich.
24. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923.
25. L. A. Carpino, J. Am. Chem. Soc. 1993, 115, 4397.
26. U. W. Bohdal, 'Synthesis and Conformational Studies of Peptides Containing α-Alkylated Aspartic and Glutamic Acids and Their Succinimide and Pyroglutamate Derivatives', Ph.D. Thesis, 1996, University of Zürich.
27. C. M. Wilmot, J. M. Thornton, J. Mol. Biol. 1988, 203, 221.
28. C. M. Wilmot, J. M. Thornton, Protein Eng. 1990, 3, 479.
29. S. Brahms, J Brahms, J. Mol. Biol. 1980, 138, 149.
30. S. Capasso, L. Mazzarella, F. Sica, A. Zagari, Int. J. Pept. Protein Res. 1984, 24, 588.
31. S. Capasso, L. Mazzarella, F. Sica, A. Zagari, Acta Crystallogr., Sect. C. Cryst. Struct. Commun. 1987, 43, 1607
32. S. Capasso, C. R. Mattia, L. Mazzarella, A. Zagari, G. Cascarano, C. Giacovazzo, Acta Crystallogr., Sect. B: Struct. Sci. 1992, 48, 285.
33. L. Mazzarella, I. Schow, F. Sica, A. Zagari, Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1988, 44, 880.
34. M. Crisma, G. Valle, C. Toniolo, S. Prasad, R. B. Rao, P. Balaram, Biopolymers 1995, 35, 1.
35. S. Prasad, R. B. Rao, P. Balaram, Biopolymers 1995, 35, 11.
36. P. Wipf, R. W. Kunz, R. Prewo, H. Heimgartner, Helv. Chim. Acta 1988, 71, 268.
37. J. H. Dyson, P. E. Wright, Annu. Rev. Biophys. Chem. 1991, 20, 519.
38. M. Hollósi, Z. S. Majer, A. Z. Ronai, A. Mahyar, K. Medzihradsky, S. Holly, A Perczel, G. D. Fasman, Biopolymers 1994, 34, 177.