A general and convenient synthesis of novel phosphotyrosine mimetics

Tetrahedron Letters

Volumn 37, Issue 21, 1996, Pages 3635-3638

  Szardenings, Anna Katrin ^a   Gordeev, Mikhail F ^a   Patel, Dinesh V ^a  

^a AFFYMAX RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; PHOSPHONOAMINO ACID; TYROSINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION ANALYSIS;

EID: 0029945906     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00666-1     Document Type: Article

References (30)

1. a) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233.
2. b) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.
3. c) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
4. d) Gordon, E. M.; Gallop, M. A., Patel , D. V. Acc. of Chem Res. 1996, in press.
5. e) Patel D. V., Gordon, E. M. Drug Discovery Today 1996, in press.
6. a) Mayer, B.J.; Baltimore, D. Trends Cell. Biol. 1993, 3, 8.
7. b) Pawson, T.; Gish, G.D. Cell 1992, 71, 359.
8. c) Birge, R.B.; Hanafusa, H. Science 1993, 262, 1522.
9. d) Ullrich, A.; Schlessinger, J. Cell 1990, 61, 203.
10. e) Lowenstein, E.J.; Daly, R.J.; Batzer, A.G. et al. Cell 1992, 70, 431.
11. f) Waksman, G.; Shoelson, S.E.; Pant, N.; Cowburn, D.; Kutiyan, J. Cell 1993, 72, 779.
12. Kitas, E. A.; Knorr, R.; Trzeciak, A.; Bannwarth, W. Helv. Chim. Acta 1991, 74, 1314.
13. a) Perich, J. W.; Johns, R.B. Synthesis 1989, 701.
14. b) Kitas, E. A.; Perich, J. W.; Tregear, G. W.; Johns, R. B. J. Org. Chem. 1990, 55, 4181.
15. c) Perich, J. W.; Johns, Reynolds, E. C. Int. J. Peptide Protein Res. 1991, 37, 572.
16. d) Kitas, E. A.; Wade, J. D.; Johns, R. B.; Perich, J. W.; Tregear, G. W. JCS., Chem. Commun. 1991, 4181.
17. N-protected dimethylphosphotyrosine has been most commonly employed in this context. However, problems such as partial demethylation of the dimethylphosphono group and dephosphorylation during peptide synthesis, as well as acid catalyzed backbone rearrangements during final deprotection of the phosphate group have been recently reported. Lee, E-S.; Cushman, M. J. Org. Chem. 1994, 59, 2086. Di-t-butyl esters have limited stability, and dibenzyl esters are stable but limited in versatility because of their susceptibility to some of the cleavage conditions commonly employed in solid phase peptide synthesis.
18. Ottinger, E.A.; Shekels, L.L.; Bernlohr, D.A.; Barany, G. Biochem. 1993, 32, 4354.
19. Gordeev, M. F.; Patel, D. V.; Barker, P. L.; Gordon, E. M. Tetrahedron. Lett. 1994, 35, 7585.
20. Alewood, P. F.; Johns, R. B.; Valerio, R. M. Synthesis, 1983, 30.
21. Beaucage, S. L.; Iyer, R. P. Tetrahedron, 1993, 49, 1925.
22. 3N.
23. 3: Stowell, J. W.; Widlanski, T. S. Tetrahedron Lett. 1995, 36, 1825.
24. 3: Oza, V. B.; Corcoran, R. C. J. Org. Chem. 1995, 60, 3680.
25. 31P NMR) and used directly for subsequent reactions.
26. These studies will be reported elsewhere in near future.
27. 31P NMR.
28. a) Deeks, T.; Crooks, P. A.; Waigh, R. D. J. Med. Chem. 1983, 26, 762.
29. b) Ornstein, P. L.; Arnold, M. B.; Augenstein, N. K.; Paschal, J. W. J. J. Org. Chem. 1991, 56, 4388.
30. c) Nicolas, E.; Russell, K. C.; Knollenberg, J.; Hruby, V. J. J. Org. Chem. 1993, 58, 7565.