An efficient strategy to orthogonally protected (R)- and (S)-α-methyl(alkyl)serine-containing peptides via a novel azlactone/oxazoline interconversion reaction

Journal of Organic Chemistry

Volumn 61, Issue 12, 1996, Pages 4080-4086

  Obrecht, Daniel ^a   Altorfer, Michael ^a,b   Lehmann, Christian ^a   Schönholzer, Peter ^a   Müller, Klaus ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001092146     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952068g     Document Type: Article

References (51)

1. Williams, R. M. Synthesis of optically active α-amino acids; Organic Chemistry Series; Pergamon: New York, 1989.
2. Duthaler, R. O. Tetrahedron 1994, 50, 1540-1650.
3. Ottenheijm, H. C. J. Chimia 1985, 39, 89.
4. Wipf, P.; Kunz, R. W.; Prewo, R.; Heimgartner, H. Helv. Chim. Acta 1988, 71, 268-273.
5. Wipf, P.; Heimgartner, H. Helv. Chim. Acta 1988, 71, 258-267.
6. Obrecht, D.; Bohdal, U.; Broger, C.; Bur, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 563-580.
7. Obrecht, D.; Karajiannis, H.; Lehmann, C.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 703-714.
8. Obrecht, D.; Bohdal, U,; Lehmann, C.; Schönholzer, P.; Müller, K. Tetrahedron 1995, 51, 10883-10900.
9. Obrecht, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Müller, K. Helv. Chim. Acta 1995, 78, 1567-1587.
10. Obrecht, D.; Spiegler, C.; Schönholzer, P.; Müller, K.; Heimgartner, H.; Stierli, F. Helv. Chim. Acta 1992, 75, 1666-1696.
11. Mutter, M. Angew. Chem. 1985, 97, 639-654.
12. Toniolo, C. CRC Crit. Rev. Biochem. 1980, 9, 1.
13. Prasad, B. V. V.; Balaram, P. CRC Crit. Rev. Biochem. 1984, 16, 307.
14. Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747.
15. Benedetti, E.; Toniolo, C.; Hardy, P.; Barone, V.; Bavoso, B.; di Blasio, B.; Grimaldi, P.; Lelj, F.; Pavone, V.; Pedone, C.; Bonora, G. M.; Lingham, I. J. Am. Chem. Soc. 1984, 106, 8146-8152.
16. Barone, V.; Lelj, F.; Bavoso, A.; di Blasio, B.; Grimaldi, P.; Pavone, V.; Pedone, C. Biopolymers 1985, 24, 1759.
17. Toniolo, C.; Benedetti, E. ISI Atlas Sci.: Biochem. 1988, 255.
18. Crisma, M.; Valle, G.; Bonora, G. M.; Toniolo, C.; Lelj, F.; Barone, V.; Fraternali, F.; Hardy, P. M.; Maia, H. L. S. Biopolymers 1991, 31, 637.
19. Müller, K.; Obrecht, D.; Knierzinger, A.; Stankovic, C.; Spiegler, C.; Bannwarth, W.; Trzeciak, A.; Englert, G.; Labhardt, A. M.; Schönholzer, P. Perspectives in Medicinal Chemistry; Testa, B., Kyburz, E., Fuhrer, W., Giger, R., Eds.; Helvetica Chimica Acta: Basel, 1993; Chapter 33, pp 513-531.
20. Ramachandran, G. N.; Sasikharan, V. Adv. Protein Chem. 1968, 23, 282.
21. Venkatachalan, C. M.; Ramachandran, G. N. Ann. Rev. Biochem. 1973, 38, 45.
22. Burgess, A. W.; Leach, S. J. Biopolymers 1973, 12, 2599-2605.
23. Cambridge Structural Database, Version 5.06, October 1993.
24. Richardson, J. S. Biophysik. J. 1992, 63, 1186-1209.
25. Ito, Y.; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T. Tetrahedron Lett. 1988, 29, 235-238.
26. Seebach, D.; Aebi, J. D. Tetrahedron Lett. 1984, 25, 2545-2548.
27. Kuo, C. H.; Wendler, N. L. Tetrahedron Lett. 1978, 3, 211-214.
28. Colson, P. J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924.
29. Fukuyama, T.; Xu, L. J. Am. Chem. Soc. 1993, 115, 8449-8450.
30. Seebach, D.; Aebi, J. D.; Gander-Goquoz, M.; Neaf, R. Helv. Chim. Acta 1987, 70, 1192-1216.
31. Zembower, D. E.; Gilbert, J. A.; Ames, M. M. J. Med. Chem. 1993, 36, 305-313.
32. Schöllkopf, U.; Hartwig, W.; Groth, U.; Westphalen, K. O. Liebigs Ann. Chem. 1981, 696-708.
33. Schöllkopf, U.; Groth, U.; Hartwig, W. Liebigs Ann. Chem. 1981, 2407-2418.
34. Coussedière, D.; Gigliotti, G,; Moguilewski, M. Appl. EP 305, 270, 1989.
35. Wipf, P.; Venkatraman, S.; Miller, C. P. Tetrahedron Lett. 1995, 36, 3639-3642.
36. Altmann, E.; Altmann, K. H.; Nebel, K.; Mutter, M. Int. J. Peptide Protein Res. 1988, 32, 344-351.
37. Pavone, V.; Di Blasio, B.; Lombardi, A.; Maglio, O.; Isernia, C.; Pedone, C.; Benedetti, E.; Altmann, E.; Mutter, M. Int. J. Pept. Protein Res. 1993, 41, 15-20.
38. Obrecht, D.; Bohdal, U.; Ruffieux, R.; Müller, K. Helv. Chim. Acta 1994, 77, 1423.
39. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
40. Meyers, A. I.; Schmidt, W.; McKennon, M. J. Synthesis 1993, 250-262.
41. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397-4398.
42. Angell, Y. M.; Garcia-Echeverria, C.; Rich, D. H. Tetrahedron Lett. 1994, 35, 5981.
43. Herzig, J.; Nudelman, A.; Gottlieb, H. E.; Fischer, B. J. Org. Chem. 1986, 57, 727-730.
44. Heine, H. W. J. Am. Chem. Soc. 1966, 78, 3708.
45. Stammer, C. H.; Wilson, A. N.; Spencer, C. F.; Bachelor, F. W.; Holly, F. W.; Folkers, K. J. Am. Chem. Soc. 1957, 79, 3236.
46. Stierli, F.; Obrecht, D.; Heimgartner, H. Chimia 1984, 38, 432.
47. Wilmot, C. M.; Thornton, J. M. J. Mol. Biol. 1988, 203, 221.
48. Wilmot, C. M.; Thornton, J. M. Protein Eng. 1990, 3, 479.
49. Wolfe, S. Acc. Chem. Res. 1972, 5, 102.
50. IUPAC-IUB Commission on Biochemical Nomenclature. Biochemistry 1970, 9, 3471.
51. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 IEZ, UK.