Abstract
Conformational analysis of two pairs of synthetic cyclodipeptides formed by interaction of both side chain functional groups (, and ) and of the main and side chains (, and ) was achieved by the method of molecular mechanics. The energetically optimal conformational states of the molecules under study were determined. It was shown that the conformational motility of cyclic system of the compounds under study depends on the relative arrangement of the amide groups and the number of atoms in the cycle.
Similar content being viewed by others
References
Abel, A., Advances in Amino Acid Mimetics and Peptidomimetics, Greenwich, CT: Jai Press, 1997.
Schneider, J.P. and Kelly, J.W., Chem. Rev., 1995, vol. 95, pp. 2169–2187.
Toniolo, C., Int. J. Pept. Protein Res., 1990, vol. 35, pp. 287–300.
Schiller, P.W., Nguyen, T.M.D., Lemieux, C., and Maziak, L.A., J. Med. Chem., 1985, vol. 28, pp. 1766–1771.
Schiller, P.W., Nguyen, T.M.D., Lemieux, C., and Maziak, L.A., J. Med. Chem., 1987, vol. 30, pp. 2094–2099.
Mierke, D.F., Schiller, P.W., and Goodman, M., Biopolymers, 1990, vol. 29, pp. 943–952.
Fry, D.C., Madison, V.S., Greeley, D.N., Felix, A.M., Heimer, E.P., Frohman, L., Campbell, R.M., Mowles, T.F., Toome, V., and Wegrzynski, B.B., Biopolymers, 1992, vol. 32, pp. 649–666.
Charpentier, B., Pelaprat, D., Durieux, C., Dor, A., Reibaud, M., Blanchard, J.C., and Roques, B.P., Proc. Natl. Acad. Sci. USA, 1988, vol. 85, pp. 1968–1972.
Charpentier, B., Dor, A., Roy, P., England, P., Pham, H., Durieux, C., and Roques, B.P., J. Med. Chem., 1989, vol. 32, pp. 1184–1190.
Roques, B.P., Biopolymers, 1992, vol. 32, pp. 407–410.
Al-Obeidi, F., Castrucci, A.M., Hadley, M.E., and Hruby, V.J., J. Med. Chem., 1989, vol. 32, pp. 2555–2561.
Rao, M.H., Yang, W., Joshua, H., Becker, J.M., and Naider, F., Int. J. Pept. Protein Res., 1995, vol. 45, pp. 418–429.
Holzemann, G., Pachler, K.G., Eberhart, B., Holzel, H., Kraft, M., and Barnickel, G., Int. J. Pept. Protein Res., 1991, vol. 37, pp. 283–292.
Schmidt, R. and Neubert, K., Int. J. Pept. Protein Res., 1991, vol. 37, pp. 502–507.
Antsans, Yu.E., Bisenietse, D.A., Vosekalna, I.A., Myshlyakova, N.V., and Chipens, G.I., Bioorg. Khim., 1990, vol. 16, pp. 358–369.
Rone, R., Manesis, N., Hassan, M., and Goodman, M., Tetrahedron, 1988, vol. 44, pp. 895–924.
Bobrova, I.V., Myshlyakova, N.V., Papsuevich, O.S., Vosekalna, I.A., and Mekshun, E.I., Bioorg. Khim., 1995, vol. 21, pp. 275–281.
Bitar, K.G., Somogyvari-Vigh, A., and Coy, D.H., Peptides, 1994, vol. 461–466.
Valero, M.L., Camarero, J.A., Adeva, A., Verdaguer, N., Fita, I., Mateu, M.G., Domingo, E., Giralt, E., and Andreu, D., Biomed. Pept. Proteins Nucleic Acids, 1995, vol. 1, pp. 133–140.
Campbell, R.M., Bongers, J., and Felix, A.M., Biopolymers, 1995, vol. 37, pp. 67–88.
Schiller, P.W., Nguyen, T.M., Maziak, L., and Lemieux, C., Biochem. Biophys. Res. Commun., 1985, vol. 127, pp. 558–564.
Heavner, G.A., Audhya, T., Doyle, D., Tjoeng, F.S., and Goldstein, G., Int. J. Pept. Protein Res., 1991, vol. 37, pp. 198–209.
Chulin, A.N., Reaction of Aminoacyl Inclusion in Synthesis of Model Cyclopeptides, Cand. Sci. (Chem.) Dissertation, Moscow: Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, RAS, 2005.
Kostetskii, P.V., Arkhipova, S.F., Artem’ev, I.V., Rodionov, I.L., Rodionova, L.N., and Ivanov, V.T., Bioorg. Khim., 1997, vol. 23, pp. 531–538.
Kostetskii, P.V. and Artem’ev, I.V., Bioorg. Khim., 1997, vol. 23, pp. 168–173.
Brooks, B.R., Bruccoleri, R.E., Olafson, B.D., States, D.J., Swaminathan, S., and Karplus, M., Comput. Chem., 1983, vol. 4, pp. 187–217.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © S.F. Arkhipova, I.V. Artem’yev, E.A. Goryacheva, V.Z. Pletnev, 2008, published in Bioorganicheskaya Khimiya, 2008, Vol. 34, No. 5, pp. 610–616.
Rights and permissions
About this article
Cite this article
Arkhipova, S.F., Artem’yev, I.V., Goryacheva, E.A. et al. Conformational analysis of cyclic dipeptides: I. , , , and . Russ J Bioorg Chem 34, 544–549 (2008). https://doi.org/10.1134/S1068162008050038
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1068162008050038