Summary
The design process and the synthetic problems for the construction of conformationally constrained cyclic somatostatins are described. Highly potent analogs containing o-aminomethylphenylacetic acid or o-aminomethylphenylalanine are obtained.
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Moreau, J.P. and DeFeudis, F.V., Life Sci., 40 (1987) 419.
Bauer, W., Briner, V., Doepfner, W., Haller, R., Huguenin, R., Marbach, P., Petcher, T. J. and Pless, J., Life Sci., 31 (1982) 1133.
Veber, D.F., In Smith, J.A. and Rivier, J.E. (Eds.) Peptides: Chemistry and Biology (Proceedings of the 12th American Peptide Symposium), ESCOM, Leiden, 1992, pp. 3–24.
Kessler, H., Bernd, M., Kogler, H., Zarbock, J., Sørensen, O.W., Bodenhausen, G. and Ernst, R.R., J. Am. Chem. Soc., 105 (1983) 6944.
Nutt, R.F., Dylion Colton, C., Veber, D.F., Slater, E.L. and Saperstein, R., Klin. Wochenschr., 64 (Suppl. VII) (1986) 71.
Fesik, S.W., Gampe, R.T., Holzman, T.F., Egan, D.A., Edalji, R., Luly, J.R., Simmer, R., Helfrich, R., Kishore, V. and Rich, D.H., Science, 250 (1990) 1406.
Van derElst, P., Van denBerg, E., Pepermans, H., Van derAuwera, L., Zeeuws, R., Tourwé, D. and VanBinst, G., Int. J. Pept. Protein Res., 29 (1987) 318.
Naito, T., Ohumura, J., Kasai, K., Masuko, K., Hoshi, H., Kamachi, H. and Kawaguchi, H., J. Antibiot., 30 (1977) 698.
Jensen, B.L. and Michaud, D.P., Synthesis, (1977) 848.
Schollkopf, U., Wick, R., Hinrichs, R. and Lampe, M., Liebigs Ann. Chem., (1988) 1025.
Flynn, D.L., Jzelle, R.E. and Grieco, P.A., J. Org. Chem., 48 (1983) 2424.
Elseviers, M., Van derAuwera, L., Tourwé, D. and VanBinst, G., Biochem. Biophys. Res. Commun., 154 (1988) 515.
Evans, D.A., Takacs, J.M., McGee, L.R., Ennis, M.D., Mathre, D.J. and Bartoli, J., Pure Appl. Chem., 53 (1981) 1109.
Huang, Z., He, Y.-B., Raynor, K., Tallent, M., Reisine, T. and Goodman, M., J. Am. Chem. Soc., 114 (1992) 9390.
Jaspers, H., Tourwé, D., VanBinst, G., Pepermans, H., Borea, P., Ucelli, L. and Salvadori, S., Int. J. Pept. Protein Res., 39 (1992) 315.
Tourwé, D., Couder, J., Cėusters, M., Meert, D., Burks, T.F., Kramer, T.H., Davis, P., Knapp, R., Yamamura, H., Leysen, J.E. and VanBinst, G., Int. J. Pept. Protein Res., 39 (1992) 131.
Tourwé, D., Verschueren, K., Jaspers, H. and VanBinst, G., In Schneider, C.H. and Eberle, A.N. (Eds.) Peptides 1992 (Proceedings of the 22nd European Peptide Symposium), ESCOM, Leiden, 1993, pp. 625–626.
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Tourwé, D. Conformation-directed design of cyclic somatostatins containing a βVI-turn mimetic. Lett Pept Sci 2, 182–186 (1995). https://doi.org/10.1007/BF00119148
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DOI: https://doi.org/10.1007/BF00119148