Summary
Glycoconjugates of leucine-enkephalin containing either a d-mannose or a d-galactose moiety coupled through an ester linkage at the C-terminus were synthesized to determine the influence of the carbohydrate moiety on the biological activity of the parent peptide. The syntheses were carried out in a stepwise manner by treating the free sugars with the activated ester of the C-terminal dipeptide in the presence of imidazole, followed by elongation of the peptide chain and removal of the protecting groups. The pure glycoconjugates were tested for opioid-like activity in the guinea pig ileum and mouse vas deferens assays and showed higher μ-agonist potency than the parent peptide.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Spillmann, D. Glycoconjugate J., 11 (1994) 169 and references cited therein.
Nishikawa, M., Miyazaki, C., Yamashita, F., Takakura, Y. and Hashida, M., Am. J. Physiol. (Gastrointest. Liver Physiol., 31) 268 (1995) G849.
Kuiper, J., Bakkeren, H.F., Biessen, E.A.L. and VanBerkel, T.J.C., Biochem. J., 299 (1994) 285.
Mullin, N.P., Hall, K.T. and Taylor, M.E., J. Biol. Chem., 269 (1994) 28405.
Ashwell, G. and Harford, J., Annu. Rev. Biochem., 51 (1982) 531.
Palomino, E., Adv. Drug Del. Rev., 13 (1994) 311.
Paulsen, H., Peters, S., Bielfeldt, T., Meldal, M. and Bock, K., Carbohydr. Res., 268 (1995) 17.
Roberge, J.Y., Beebe, X. and Danishefsky, S.J., Science, 269 (1995) 202.
Rademann, J. and Schmidt, R.R., Carbohydr. Res., 269 (1995) 217.
BarchiJr., J.J., Russ, P., Johnson, B., Otaka, A., Nomizu, M. and Yamada, Y., Bioorg. Med. Chem. Lett. 5 (1995) 711.
Skurić, M., Horvat, J., Horvat, Š., Chung, N.N. and Schiller, P.W., Int. J. Pept. Protein Res., 43 (1994) 402 and references cited therein.
Horvat, J., Horvat, Š., Lemieux, C. and Schiller, P.W., Int. J. Pept. Protein Res. 31 (1988) 499.
Waterfield, A.A., Leslie, F.M., Lord, J.A.H., Ling, N. and Kosterlitz, H.W., Eur. J. Pharmacol., 58 (1979) 11.
DiMaio, J., Nguyen, M.-D., Lemieux, C. and Schiller, P.W., J. Med. Chem., 25 (1982) 1432.
Chawkin, C. James, I.F. and Goldstein, A., Science, 215 (1982) 413.
Angyal, S.J., Carbohydr. Res., 263 (1994) 1.
Horvat, Š., Horvat, J. and Klaić, B., Croat. Chim. Acta, 65 (1992) 907.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Horvat, Š., Varga-Defterdarović, L., Horvat, J. et al. Alterations in biological activities induced by glycation of leucine-enkephalin with different monosaccharide moieties. Lett Pept Sci 2, 363–368 (1996). https://doi.org/10.1007/BF00120000
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00120000