The "azirine/oxazolone method" under solid-phase conditions

European Journal of Organic Chemistry

Volumn , Issue 18, 2004, Pages 3820-3827

  Stamm, Simon ^a   Heimgartner, Heinz ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

Aminoisobutyric acid (Aib); Azirine; Inverse peptide synthesis; Oxazolone method; Peptides; Solid phase synthesis

Indexed keywords

2 AMINO 2 METHYLPROPIONIC ACID; 2H AZIRIN 3 AMINE; ALANINE; AZIRINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; OXAZOLONE; PHENYLALANINE; PHOSGENE; REAGENT; SYNTHETIC PEPTIDE; TOLUENE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CAPILLARY GAS CHROMATOGRAPHY; ENANTIOMER; EPIMERIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PEPTIDE SYNTHESIS; RACEMIZATION; SOLID; STEREOSPECIFICITY;

EID: 4644291269     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400330     Document Type: Article

References (55)

1. R. B. Merrifield, J. Am. Chem. Soc. 1963, 85, 2149-2154.
2. G. B. Fields, R. L. Noble, Int. J. Pept. Protein Res. 1990, 35, 161-214.
3. P. Lloyd-Williams, F. Alberico, E. Giralt, Tetrahedron 1993, 49, 11065-11133.
4. W. G. Gutheil, Q. Xu, Chem. Pharm. Bull. 2002, 50, 688-691.
5. R. L. Letsinger, M. J. Kornet, J. Am. Chem. Soc. 1963, 85, 3045-3046.
6. A. M. Felix, R. B. Merrifield, J. Am. Chem. Soc. 1970, 92, 1385-1391.
7. B. Henkel, L. Zhang, E. Bayer, Liebigs Ann./Recueil 1997, 2161-2168.
8. A. Johansson, E. Åkerblom, K. Ersmark, G. Lindeberg, A. Hallberg, J. Comb. Chem. 2000, 2, 496-507.
9. F. Bordusa, D. Ullmann, H.-D. Jakubke, Angew. Chem. Int. Ed. Engl. 1997, 36, 1099-1101.
10. H. Wenschuh, M. Beyermann, E. Krause, M. Brudel, R. Winter, M. Schümann, L. A. Carpino, M. Bienert, J. Org. Chem. 1994, 59, 3275-3280.
11. H. Wenschuh, M. Beyermann, H. Haber, J. K. Seydel, E. Krause, M. Bienert, L. A. Carpino, A. El-Faham, F. Alberico, J. Org. Chem. 1995, 60, 405-410.
12. M. Meldal, M. A. Juliano, A. M. Jansson, Tetrahedron Lett. 1997, 38, 2531-2534.
13. W. F. DeGrado, Adv. Prot. Chem. 1988, 39, 51-124.
14. J. Rizo, L. M. Gierasch, Annu. Rev. Biochem. 1992, 61, 387-416.
15. V. J. Hruby, F. Al-Obeidi, W. Kazmierski, Biochem. J. 1990, 268, 249-262.
16. M. Mutter, Angew. Chem. Int. Ed. Engl. 1985, 24, 639-653.
17. W. Mayr, G. Jung, J. Strähle, Liebigs Ann. Chem. 1980, 715-724.
18. U. Slomczynska, D. D. Beusen, J. Zabrocki, K. Kociolek, A. Redlinski, F. Reusser, W. C. Hutton, M. T. Leplawy, G. R. Marshall, J. Am. Chem. Soc. 1992, 114, 4095-4106.
19. S. Vijayalakshmi, R. Balaji Rao, I. L. Karle, P. Balaram, Biopolymers 2000, 53, 84-98.
20. N. Lancelot, K. Elbayed, J. Raya, M. Piotto, J.-P. Briand, F. Formaggio, C. Toniolo, A. Bianco, Chem. Eur. J. 2003, 9, 1317-1323.
21. H. Heimgartner, Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264.
22. J. M. Humphrey, A. R. Chamberlin, Chem. Rev. 1997, 97, 2243-2266.
23. P. Wipf, H. Heimgartner, Helv. Chim. Acta 1990, 73, 13-24.
24. R. T. N. Luykx, A. Linden, H. Heimgartner, Helv. Chim. Acta 2003, 86, 4093-4111.
25. N. Pradeille, H. Heimgartner, J. Pept. Sci. 2003, 9, 827-837.
26. S. Stamm, A. Linden, H. Heimgartner, Helv. Chim. Acta 2003, 86, 1371-1396.
27. J. Lehmann, A. Linden, H. Heimgartner, Tetrahedron 1998, 54, 8721-8736.
28. C. B. Bucher, H. Heimgartner, Helv. Chim. Acta 1996, 79, 1903-1915.
29. After PyBOP-mediated coupling of carboxylpolystyrene and H-Ala-OtBu, the tBu ester was hydrolyzed in TFA/DCM. The resin was treated, the tBu ester was hydrolyzed in TFA/DCM. 3-amine (2), the terminal amide was then hydrolyzed with 3 M HCI, and PyBOP-mediated coupling with H-Phe-OtBu finally yielded the resin-bound tripeptide Ala-Aib-Phe-OtBu. After every reaction, the resin was examined by ATR-FT-IR spectroscopy. Acidic hydrolysis (propionic acid/HCl, 130 °C) of the resin-bound tripeptide gave Ala, Aib and Phe, which were detected by ESI-MS.
30. S. R. Chhabra, A. N. Khan, B. W. Bycroft, Tetrahedron Lett. 1998, 39, 3585-3588.
31. R. L. Letsinger, M. J. Kornet, V. Mahadevan, D. M. Jerina, J. Am. Chem. Soc. 1964, 5163-5165.
32. D. J. Burdick, M. E. Struble, J. P. Burnier, Tetrahedron Lett. 1993, 34, 2589-2592.
33. J. R. Hauske, P. Dorff, Tetrahedron Lett. 1995, 36, 1589-1592.
34. B. Raju, T. P. Kogan, Tetrahedron Lett. 1997, 38, 3373-3376.
35. F. Wang, J. R. Hauske, Tetrahedron Lett. 1997, 38, 6529-6532.
36. B. A. Dressman, L. A. Spangle, S. W. Kaldor, Tetrahedron Lett. 1996, 37, 937-940.
37. C. Y. Ho, M. J. Kukla, Tetrahedron Lett. 1997, 38, 2799-2802.
38. R. Léger, R. Yen, M. W. She, V. J. Lee, S. J. Hecker, Tetrahedron Lett. 1998, 39, 4171-4174.
39. W. J. N. Meester, F. P. J. T. Rutjes, P. H. H. Hermkens, H. Hiemstra, Tetrahedron Lett. 1999, 40, 1601-1604.
40. Some loss of peptide was observed during deprotection of tBu esters with TFA on hydroxymethyl polystyrene resin. When hydroxyethylpolystyrene resin was used no cleavage from the support was achieved with either trifluoromethanesulfonic acid or HBr in acetic acid.
41. Performed by C. A. T. GmbH & Co., Tübingen, Germany.
42. Interchim Uptisphere HDO C18, 120 A, 3 μm, 200 × 2.0 mm.
43. 2O was added. The solution was stirred at room temp. and then concentrated in vacuo.
44. "Special Issue: Peptaibols/Peptaibiotics": H. Brückner (Ed.), J. Pept. Sci. 2003, 9, 663-837.
45. H. Wenschuh, M. Beyermann, E. Krause, L. A. Carpino, M. Bienert, Innovation Perspect. Solid Phase Synth. Collect. Pap., Int. Symp., 3rd (1994), Meeting Date 1993, 697-700.
46. H. Wenschuh, M. Beyermann, S. Rothemund, L. A. Carpino, M. Bienert, Tetrahedron Lett. 1995, 36, 1247-1250.
47. H. Gausepohl, M. Kraft, R. W. Frank, Int. J. Pept. Protein Res. 1989, 34, 287-294.
48. +) was detected. Probably the amide group in the side chain of Gln had partially hydrolyzed in 3 M HCl, so that two molecules of Val could add in the subsequent coupling reaction.
49. M. Crisma, A. Barazza, F. Formaggio, B. Kaptein, Q. Broxtermánn, J. Kamphuis, C. Toniolo, Tetrahedron 2001, 57, 2813-2825.
50. A. Jaworski, H. Brückner, J. Pept. Sci. 2001, 7, 433-447.
51. J. M. Villalgordo, H. Heimgartner, Tetrahedron 1993, 49, 7215-7222.
52. J. M. Villalgordo, H. Heimgartner, Helv. Chim. Acta 1993, 76, 2830-2837.
53. F. C. Westall, J. Scotchler, A. B. Robinson, J. Org. Chem. 1972, 37, 3363-3365.
54. 3).
55. S. R. Chhabra, H. Parekh, A. N. Khan, B. W. Bycroft, B. Kellam, Tetrahedron Lett. 2001, 42, 2189-2192.