The 'azirine/oxazolone method' on solid phase: Introduction of various α,α-disubstituted α-amino acids

Helvetica Chimica Acta

Volumn 89, Issue 1, 2006, Pages 1-15

  Stamm, Simon ^a   Linden, Anthony ^a   Heimgartner, Heinz ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AROMATIC COMPOUNDS; CARBOXYLIC ACIDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

AMINOCYCLOPENTANE; AMINOISOBUTYRIC ACID; OXAZOLONE METHOD; PEPTIDES;

AMINO ACIDS;

2 AMINO 2 METHYLPROPIONIC ACID; 3 AMINO 3,4,5,6 TETRAHYDRO 2H PYRAN 3 CARBOXYLIC ACID; ALPHA AMINO ACID; ALPHA METHYLPHENYLALANINE; AZIRINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYCLOLEUCINE; OXAZOLONE; PHENYLALANINE DERIVATIVE; SYNTHETIC PEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 31344454289     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200690019     Document Type: Article

References (40)

1. W. F. DeGrado, Adv. Prot. Chem. 1988, 39, 51.
2. J. Rizo, L. M. Gierasch, Annu. Rev. Biochem. 1992, 61, 387.
3. V. J. Hruby, F. Al-Obeidi, W. Kazmierski, Biochem. J. 1990, 268, 249.
4. M. Mutter, Angew. Chem., Int. Ed. 1985, 24, 639.
5. H. Heimgartner, Angew. Chem., Int. Ed. 1991, 30, 238.
6. J. M. Humphrey, A. R. Chamberlin, Chem. Rev. 1997, 97, 2243.
7. P. Wipf, H. Heimgartner, Helv. Chim. Acta 1986, 69, 1153;
8. P. Wipf, H. Heimgartner, Helv. Chim. Acta 1987, 70, 354.
9. N. Pradeille, A. Linden, K. Möhle, O. Zerbe, H. Heimgartner, Chem. Biodiv. 2005, 2, 1127.
10. R. T. N. Luykx, A. Linden, H. Heimgartner, Helv. Chim. Acta 2003, 86, 4093.
11. N. Pradeille, H. Heimgartner, J. Pept. Sci. 2003, 9, 827.
12. S. Stamm, A. Linden, H. Heimgartner, Helv. Chim. Acta 2003, 86, 1371.
13. J. Lehmann, A. Linden, H. Heimgartner, Tetrahedron 1998, 54, 8721.
14. C. B. Bucher, H. Heimgartner, Helv. Chim. Acta 1996, 79, 1903.
15. W. Altherr, Ph.D. thesis, Universität Zürich, 1994.
16. P. Wipf, H. Heimgartner, Helv. Chim. Acta 1990, 73, 13.
17. S. Stamm, H. Heimgartner, Eur. J. Org. Chem. 2004, 3820.
18. C. K. Johnson, ORTEPII, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.
19. J. Bernstein, R. E. Davis, L. Shimoni, N.-L. Chang, Angew. Chem., Int. Ed. 1995, 34, 1555.
20. Performed by C.A.T. GmbH & Co., Tübingen, Germany.
21. I. Dannecker-Dörig, Ph.D. thesis, Universität Zürich, 1995.
22. S. A. Stoykova, Ph.D. thesis, Universität Zürich, 2004.
23. L. Zhang, C. Goldammer, B. Henkel, F. Zuehl, G. Panhaus, G. Jung, E. Bayer, in 'Innovation Per-spect. Solid Phase Synth. Collect. Pap.', 3rd Int. Symp. (1993), 1994, p. 711.
24. J. M. Villalgordo, H. Heimgartner, Tetrahedron 1993, 49, 7215.
25. J. M. Villalgordo, H. Heimgartner, Helv. Chim. Acta 1993, 76, 2830.
26. C. Strässler, A. Linden, H. Heimgartner, Helv. Chim. Acta 1997, 80, 1528.
27. C. B. Bucher, A. Linden, H. Heimgartner, Helv. Chim. Acta 1995, 78, 935.
28. R. Hooft, KappaCCD Collect Software, Nonius BV, Delft, The Netherlands, 1999.
29. Z. Otwinowski, W. Minor, in 'Methods in Enzymology', Vol. 276, 'Macromolecular Crystallography', Part A, Eds. C. W. Carter Jr., R. M. Sweet, Academic Press, New York, 1997, p. 307.
30. R. H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33.
31. G. M. Sheldrick, SHELXS97, Program for the Solution of Crystal Structures, University of Göttingen, Germany, 1997.
32. A. L. Spek, PLATON, Program for the Analysis of Molecular Geometry, University of Utrecht, The Netherlands, 2005.
33. a) H. D. Flack, G. Bernardinelli, Acta Crystallogr., Sect A 1999, 55, 908;
34. b) H. D. Flack, G. Bernar-dinelli, J. Appl. Crystallogr. 2000, 33, 1143.
35. a) E. N. Maslen, A. G. Fox, M. A. O'Keefe, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 6.1.1.1, p. 477;
36. b) D. C. Creagh, W. J. McAuley, 'International Tables for Crystallography', ibid. Table 4.2.6.8, p. 219;
37. c) D. C. Creagh, J. H. Hubbell, 'International Tables for Crystallography', ibid. Table 4.2.4.3, p. 200.
38. R. F. Stewart, E. R. Davidson, W. T. Simpson, J. Chem. Phys. 1965, 42, 3175.
39. J. A. Ibers, W. C. Hamilton, Acta Crystallogr. 1964, 17, 781.
40. G. M. Sheldrick, SHELXL97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.