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EnglishStarting from the structure of Endomorphin-1 (Tyr-Pro-Trp-PheNH2), the endogenous ligand of mu-opioid receptor, we prepared modified peptides and peptidomimetics by introduction of unnatural amino acids, halogenation of the Trp, introduction of Pro-analogues, lipidization, and size reduction. The syntheses of (S)- or (R)-halo-tryphtophans and other Trp-analogues have been performed by tandem 1,4-addition and stereoselective enolate protonation of DHA-containing peptides. Otherwise, substituted tryphtophans have been prepared in optically pure form by enzymatic resolution. Oxazolidin-2-one 4-carboxylate has been introduced in position 2 of endomorphin-1 as a proline mimetic, to give a trans conformation of the Tyr1-Xaa2 peptide bond. Lipidization and a rationale search for focused structure modifications lead to the endomorphin mimetic N-Ac-D-Trp-Phe-Gly-NH2 and halo-substituted derivatives
| Titolo: | DESIGN AND SYNTHESIS OF OPIOID PEPTIDE ANALOGUES AND MIMETICS |
| Autore/i: | DE MARCO, ROSSELLA; GENTILUCCI, LUCA; TOLOMELLI, ALESSANDRA; S. Feddersen; SPAMPINATO, SANTI MARIO; BEDINI, ANDREA; R. Artali |
| Autore/i Unibo: | |
| Anno: | 2011 |
| Rivista: | |
| Abstract: | Starting from the structure of Endomorphin-1 (Tyr-Pro-Trp-PheNH2), the endogenous ligand of mu-opioid receptor, we prepared modified peptides and peptidomimetics by introduction of unnatural amino acids, halogenation of the Trp, introduction of Pro-analogues, lipidization, and size reduction. The syntheses of (S)- or (R)-halo-tryphtophans and other Trp-analogues have been performed by tandem 1,4-addition and stereoselective enolate protonation of DHA-containing peptides. Otherwise, substituted tryphtophans have been prepared in optically pure form by enzymatic resolution. Oxazolidin-2-one 4-carboxylate has been introduced in position 2 of endomorphin-1 as a proline mimetic, to give a trans conformation of the Tyr1-Xaa2 peptide bond. Lipidization and a rationale search for focused structure modifications lead to the endomorphin mimetic N-Ac-D-Trp-Phe-Gly-NH2 and halo-substituted derivatives |
| Data prodotto definitivo in UGOV: | 3-giu-2013 |
| Appare nelle tipologie: | 1.06 Abstract in rivista |
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