Design and synthesis of conformationally constrained, extended and reverse turn pseudopeptides as Grb2-SH2 domain antagonists

Tetrahedron Letters

Volumn 44, Issue 8, 2003, Pages 1571-1574

  Plake, Hilary R ^a   Sundberg, Thomas B ^a   Woodward, Angela R ^a   Martin, Stephen F ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

Conformational constraints; Cyclopropanes; Peptide mimics; SH2 domain

Indexed keywords

CYCLOPROPANE; GROWTH FACTOR RECEPTOR BOUND PROTEIN 2; PEPTIDE; PHOSPHOTYROSINE; PSEUDOPEPTIDE; TRIPEPTIDE;

ARTICLE; CONFORMATION; PEPTIDE SYNTHESIS; PROTEIN DOMAIN;

EID: 0037450487     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00013-3     Document Type: Article

References (38)

1. For reviews of constrained peptide mimics, see: (a) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267;
2. (b) Gante, J. Angew. Chem., Int. Ed. Eng. 1994, 33, 1699-1720;
3. (c) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854;
4. (d) Goodman, M.; Zhang, J. Chemtracts-Org. Chem. 1997, 10, 629-645.
5. DeGrado W.F. Adv. Protein Chem. 39:1988;51-124.
6. Kahn M. Synlett. 1993;821-826.
7. Olson G.L., Bolin D.R., Bonner M.P., Bös M., Cook C.M., Fry D.C., Graves B.J., Hatada M., Hill D.E., Kahn M., Madison V.S., Rusieck V.K., Sarabu R., Sepinwall J., Vincent J.P., Voss M.E. J. Med. Chem. 36:1993;3039-3059.
8. Schneider J.P., Kelley J.W. Chem. Rev. 95:1995;2169-2187.
9. (a) Martin S.F., Austin R.E., Oalmann C.J., Baker W.R., Condon S.L., DeLara E., Rosenberg S.H., Spina K.P., Stein H.H., Cohen J., Kleinert H.D. J. Med. Chem. 35:1992;1710-1721.
10. (b) Baker W.R., Jae H.-S., Martin S.F., Condon S.L., Stein H.H., Cohen J., Kleinert H.D. Bioorg. Med. Chem. Lett. 2:1992;1405-1410.
11. (c) Martin S.F., Oalmann C.J., Liras S. Tetrahedron. 49:1993;3521-3532.
12. (d) Martin S.F., Dorsey G.O., Gane T.H., Hillier M., Kessler H., Baur M., Mathä B., Erickson J.W., Bhat T.N., Munshi S., Gulnik S.V., Topol I.A. J. Med. Chem. 1998, 41, 1581-1597;
13. (e) Hillier, M. C.; Martin, S. F. In Methods in Molecular Medicine: Vol. 30, Peptidomimetics Protocols; Kazmierski, W. M.; Walker, J. M., Eds.; Humana Press: Totowa, NJ, 1999; pp. 397-406;
14. (f) Dwyer, M. P.; Martin, S. F. In Methods in Molecular Medicine: Vol. 30, Peptidomimetics Protocols, Kazmierski, W. M.; Walker, J. M., Eds.; Humana Press: Totowa, NJ, 1999; pp. 407-416;
15. (g) Martin S.F., Dwyer M.P., Hartmann B., Knight K.S. J. Org. Chem. 2000, 65, 1305-1318;
16. (h) Hillier M.C., Davidson J.P., Martin S.F. J. Org. Chem. 2001, 66, 1657-1671;
17. (i) Reichelt A., Gaul C., Frey R.R., Kennedy A., Martin S.F. J. Org. Chem. 2002, 67, 4062-4075.
18. Davidson J.P., Lubman O., Rose T., Waksman G., Martin S.F. J. Am. Chem. Soc. 124:2002;205-215.
19. Sharp K. Protein Sci. 10:2001;661-667.
20. Liu L., Guo Q.-X. Chem. Rev. 101:2001;673-696.
21. Dunitz J.D. Chem. Biol. 2:1995;709-712.
22. Rahuel J., Gay B., Erdmann D., Strauss A., Garcia E., Furet P., Caravatti G., Fretz H., Schoepfer J., Gruetter M.G. Nature Struct. Biol. 3:1996;586-589.
23. Ettmayer P., France D., Gounarides J., Jarosinski M., Martin M.-S., Rondeau J.-M., Sabio M., Topiol S., Weidmann B., Zurini M., Bair K.W. J. Med. Chem. 42:1999;971-980.
24. Garcia-Echeverria C., Gay B., Rahuel J., Furet P. Bioorg. Med. Chem. Lett. 9:1999;2915-2920.
25. Gao Y., Wei C.-Q., Burke T.R. Jr. Org. Lett. 3:2001;1617-1620.
26. Davidson J.P., Martin S.F. Tetrahedron Lett. 41:2000;9459-9464.
27. 1H NMR spectroscopy.
28. 2O): δ 7.17-7.09 (comp m, 4 H), 4.57 (dd, J=7.7, 6.1 Hz, 1 H), 3.96 (d, J=7.8 Hz, 1 H), 3.13-3.08 (m, 1 H), 2.81-2.77 (comp m, 3 H), 2.68-2.65, (m, 3 H), 2.64 (s, 3 H), 2.53-2.41 (comp m, 2 H), 1.93 (app hep, J=6.8 Hz, 1 H), 0.85 (d, J=6.8 Hz, 6 H).
29. Doyle M.P., Austin R.E., Bailey A.S., Dwyer M.P., Dyatkin A.B., Kalinin A.V., Kwan M.M.Y., Liras S., Oalmann C.J., Pieters R.J., Protopopva M.N., Raab C.E., Roos G.H.P., Zhou Q.-L., Martin S.F. J. Am. Chem. Soc. 117:1995;5763-5775.
30. For related N-alkylations, see: Chapman, K. T.; Kopka, I. E.; Durette, P. L.; Esser, C. K.; Lanza, T. J.; Izquierdo-Martin, M.; Niedzwiecki, L.; Chang, B.; Harrison, R. K.; Kuo, D. W.; Lin, T.-Y.; Stein, R. L.; Hagmann, W. K. J. Med. Chem. 1993, 36, 4293-4301. See also Refs. 3g,i.
31. Englert H.C., Gerlach U., Goegelein H., Hartung J., Heitsch H., Mania D., Scheidler S. J. Med. Chem. 44:2001;1085-1098.
32. Llinas-Brunet M., Beaulieu P.L., Cameron D.R., Ferland J.-M., Gauthier J., Ghiro E., Gillard J., Gorys V., Poirier M., Rancourt J., Wernic D., Betageri R., Cardozo M., Jakes S., Lukas S., Patel U., Proudfoot J., Moss N. J. Med. Chem. 42:1999;722-729.
33. 2O): δ 7.22 (d, J=8.5 Hz, 2 H), 7.19 (d, J=8.5 Hz, 2 H), 4.52-4.49 (m, 1 H), 3.52-3.49 (m, 1 H), 3.14-2.89 (comp m, 2 H), 2.62 (dd, J=15.0, 5.7, 1 H), 2.53 (dd, J=15.0, 8.0 Hz, 1 H), 2.30 (d, J=6.0 Hz, 1 H), 2.00 (d, J=6.0 Hz, 1 H), 1.95 (s, 3 H), 1.03 (s, 3 H), 0.93 (s, 3 H).
34. Fukuyama T., Lin S., Li L. J. Am. Chem. Soc. 112:1990;7050-7051.
35. Han Y., Chorev M. J. Org. Chem. 64:1999;1972-1978.
36. 1H NMR.
37. 2O): δ 7.27 (d, J=8.2 Hz, 2 H), 7.17 (d, J=8.2 Hz, 2 H), 4.57 (dd, J=8.4, 7.0 Hz, 1 H), 4.26 (dd, J=7.7, 4.9 Hz, 1 H), 3.98-3.94 (m, 1 H), 3.21 (dd, J=12.9, 4.3 Hz, 1 H), 3.13 (dd, J=13.9, 7.0 Hz, 1 H), 3.05-2.97 (m, 2 H), 2.95-2.87 (m, 2 H), 1.96 (s, 3 H), 1.90-1.84 (m, 1 H), 0.88 (dd, J=16.9, 6.8 Hz, 6 H).
38. Binding constants were determined using isothermal titration calorimetry following the procedure outlined in: McNemar C., Snow M.E., Windsor W.T., Prongay A., Mui P., Zhang R., Durkin J., Le H.V., Weber P.C. Biochemistry. 36:1997;10006-10014.