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Synthesis and binding properties of endomorphin-2analogs containing α-hydroxymethyl amino acids

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Abstract

Novel endomorphin-2 analogs containing the unusual amphiphilic amino acid (R)- and (S)-α-hydroxymethyltyrosine in position 1 and (R)- and (S)-α-hydroxymethylphenylalanine in the positions 3 and 4 were synthesized via the solid-phase method. The binding characteristics of the synthetic analogs may suggest that α-hydroxymethyl substitution of aminoacid residues influences the conformation of a peptide much more than simply increasing the local amphiphilic character of the peptide.

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References

  1. Corbett, A.D., Paterson, S.J. and Kosterlitz, H.W., In Herz, A. (Ed.) Opioids I (Handbook of Experimentel Pharmacology), Vol. 104/1, Springer, New York, NY, 1993, p. 645.

    Google Scholar 

  2. Zadina, J.E., Hackler, L., Ge, L.J. and Kastin, J.A.J., Nature, 386 (1997) 499.

    Google Scholar 

  3. Erchegyi, J., Kastin, A.J. and Zadina, J.E., Peptides, 13 (1993) 623.

    Google Scholar 

  4. Hackler, L., Kastin, A.J., Erchegyi, J. and Zadina, J.E., Neuropeptides, 24 (1993) 159.

    Google Scholar 

  5. Misicka, A., Lipkowski, A.W., Stropova, D., Davis, P., Porreca, F., Yamamura, H.I. and Hruby, V., Lett. Pept. Sci., 2 (1995) 203.

    Google Scholar 

  6. Olma, A., Misicka, A., Tourwé, D. and Lipkowski, A.W., Lett. Pept. Sci., 5 (1998) 383.

    Google Scholar 

  7. Misicka, A., Olma, A., Sagan, S., Tourwé, D. and Lipkowski, A.W., In Ramage, R. and Epton, R. (Eds.) Peptides 1996 (Proceedings of the 24th European Peptide Symposium), Mayflower Scientific, Kingswinford, 1998, p. 655.

    Google Scholar 

  8. Olma, A. and Tourwé, D., In Bajusz, S. and Hudecz, F. (Eds.) Peptides 1998 (Proceedings of the 25th European Peptide Symposium), Akademiai Kiado, Budapest, 1999, p. 472.

    Google Scholar 

  9. Kaminski, Z.J. and Leplawy, M.T., Synthesis, (1974) 292.

  10. Wieczorek, W., Bukowska-Strzyzewska, M., Leplawy, M.T. and Olma, A., J. Crystallogr. Spectrosc. Res., 21 (1991) 209.

    Google Scholar 

  11. Olma, A., Pol. J. Chem., 70 (1996) 1442.

    Google Scholar 

  12. Keller, O., Keller, W.E., van Look, G. and Wersin, G., Org. Synth., 63 (1985) 160.

    Google Scholar 

  13. Tourwé, D., Mannekens, E., Diem, T.N.T., Verheyden, P., Jaspers, H., Tóth, G., Péter, A., Kertész, I., Török, G., Chung, N.N. and Schiller, P.W., J. Med. Chem., 41 (1998) 5167.

    Google Scholar 

  14. Crisma, M., Valle, G., Toniolo, C., Prasad, S., Rao, R.B. and Balaram, P., Biopolymers, 35 (1994) 1.

    Google Scholar 

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Correspondence to Aleksandra Olma.

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Olma, A., Tourwé, D. Synthesis and binding properties of endomorphin-2analogs containing α-hydroxymethyl amino acids. Letters in Peptide Science 7, 93–96 (2000). https://doi.org/10.1023/A:1008906527082

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  • DOI: https://doi.org/10.1023/A:1008906527082

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