Introduction of the Aib-Pro unit into peptides by means of the 'azirine/oxazolone method' on solid phase

Tetrahedron

Volumn 62, Issue 41, 2006, Pages 9671-9680

  Stamm, Simon ^a   Heimgartner, Heinz ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

Aminoisobutyric acid; Azirine oxazolone method; Peptaibols; Peptide synthesis; Photocleavable linker

Indexed keywords

AMINO ACID; AZIRINE DERIVATIVE; OXAZOLONE; PEPTIDE DERIVATIVE; RESIN;

ARTICLE; CARBOXY TERMINAL SEQUENCE; POLYMERIZATION; PRIORITY JOURNAL; PROTEIN DEGRADATION; SOLID; SYNTHESIS; ULTRAVIOLET RADIATION;

EID: 33748059850     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.07.082     Document Type: Article

References (42)

1. Heimgartner H. Angew. Chem., Int. Ed. Engl. 30 (1991) 238-264
2. Wipf, P. Ph.D. thesis, Universität Zürich, 1987.
3. Wipf P., and Heimgartner H. Helv. Chim. Acta 71 (1988) 140-154
4. Wipf P., and Heimgartner H. Helv. Chim. Acta 73 (1990) 13-24
5. Strässler C., Linden A., and Heimgartner H. Helv. Chim. Acta 80 (1997) 1528-1554
6. Suter G., Stoykova S.A., Linden A., and Heimgartner H. Helv. Chim. Acta 83 (2000) 2961-2974
7. Stamm S., Linden A., and Heimgartner H. Helv. Chim. Acta 86 (2003) 1371-1396
8. Altherr W., and Heimgartner H. In: Giralt E., and Andreu D. (Eds). Peptides 1990 (1991), ESCOM, Leiden 107
9. Luykx R., Bucher C.B., Linden A., and Heimgartner H. Helv. Chim. Acta 79 (1996) 527-540
10. Bucher C.B., and Heimgartner H. Helv. Chim. Acta 79 (1996) 1903-1915
11. Pradeille N., and Heimgartner H. J. Pept. Sci. 9 (2003) 827-837
12. Luykx R., Linden A., and Heimgartner H. Helv. Chim. Acta 86 (2003) 4093-4111
13. Pradeille N., Zerbe O., Möhle K., Linden A., and Heimgartner H. Chem. Biodivers. 2 (2005) 1127-1152
14. Lehmann J., Linden A., and Heimgartner H. Tetrahedron 54 (1998) 8721-8736
15. Lehmann J., and Heimgartner H. Helv. Chim. Acta 82 (1999) 1899-1915
16. Breitenmoser R., Linden A., and Heimgartner H. Helv. Chim. Acta 85 (2002) 990-1018
17. Jeremic T., Linden A., and Heimgartner H. Chem. Biodivers. 1 (2004) 1730-1761
18. Jeremic T., Linden A., Möhle K., and Heimgartner H. Tetrahedron 61 (2005) 1871-1883
19. Villalgordo J.M., and Heimgartner H. Helv. Chim. Acta 80 (1997) 748-766
20. Koch K.N., Linden A., and Heimgartner H. Helv. Chim. Acta 83 (2000) 233-257
21. Koch K.N., and Heimgartner H. Helv. Chim. Acta 83 (2000) 1881-1900
22. Iliev B., Linden A., Kunz R., and Heimgartner H. Tetrahedron 62 (2006) 1079-1094
23. Köttgen P., Linden A., and Heimgartner H. Helv. Chim. Acta 89 (2006) 731-746
24. Stamm S., and Heimgartner H. Eur. J. Org. Chem. (2004) 3820-3827
25. Stamm S., Linden A., and Heimgartner H. Helv. Chim. Acta 89 (2006) 1-15
26. Brückner H., Kripp T., and Kiess M. In: Giralt E., and Andreu D. (Eds). Peptides 1990 (1991), ESCOM, Leiden 387
27. Auvin-Guette C., Rebuffat S., Prigent Y., and Bodo B. J. Am. Chem. Soc. 114 (1992) 2170-2174
28. Das M.K., Raghothamma S., and Balaram P. Biochemistry 25 (1986) 7110-7117
29. Stamm, S.; Heimgartner, H. Helv. Chim. Acta, in press.
30. Kunz H., and Dombo B. Angew. Chem., Int. Ed. Engl. 27 (1988) 711-713
31. Hiersemann M. Tetrahedron 55 (1999) 2625-2638
32. Kaljuste K., and Undén A. Tetrahedron Lett. 37 (1996) 3031-3034
33. Nicolaou K.C., Petasis N., and Seitz S. J. Chem. Soc., Chem. Commun. (1981) 1195-1196
34. Holmes C.P., and Jones D.G. J. Org. Chem. 60 (1995) 2318-2319
35. Holmes C.P. J. Org. Chem. 62 (1997) 2370-2380
36. For a review about photolabile protecting groups and linkers, see:. Bochet C.G. J. Chem. Soc., Perkin Trans. 1 (2002) 125-142
37. Patchornik A., Amit B., and Woodward R.B. J. Am. Chem. Soc. 92 (1970) 6333-6335
38. Dessolin M., Guillerez M.-G., Thieriet N., Guibé F., and Loffet A. Tetrahedron Lett. 36 (1995) 5741-5744
39. For solution phase syntheses of Trichovirin I, see:. Brückner H., and Koza A. Amino Acids 24 (2003) 311-323 and Ref. 12
40. Villalgordo J.M., and Heimgartner H. Tetrahedron 49 (1993) 7215-7222
41. Villalgordo J.M., and Heimgartner H. Helv. Chim. Acta 76 (1993) 2830-2837
42. Strazzolini P., Melloni T., and Giumanini A.G. Tetrahedron 57 (2001) 9033-9043