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Issue 9, 2003
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Stability against enzymatic hydrolysis of endomorphin-1 analogues containing β-proline

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Abstract

The enantiomer of endomorphin-1 (Tyr-Pro-Trp-PheNH2) and the analogues containing (S)- or (R)-β-proline have been synthesized, and their affinities towards μ-opioid receptors have been measured. As expected, the incubations of the different peptides with some commercially available enzymes showed that the presence of D-residues gave strong resistance towards digestion. The presence of β-proline alone is sufficient to confer good resistance against the hydrolysis of the biologically strategic Pro–Trp bond.

Graphical abstract: Stability against enzymatic hydrolysis of endomorphin-1 analogues containing β-proline

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Publication details

The article was received on 06 Feb 2003, accepted on 10 Mar 2003 and first published on 27 Mar 2003


Article type: Paper
DOI: 10.1039/B301507F
Org. Biomol. Chem., 2003,1, 1498-1502

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    Stability against enzymatic hydrolysis of endomorphin-1 analogues containing β-proline

    G. Cardillo, L. Gentilucci, A. Tolomelli, M. Calienni, A. R. Qasem and S. Spampinato, Org. Biomol. Chem., 2003, 1, 1498
    DOI: 10.1039/B301507F

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