Design and Synthesis of Small Libraries of Peptidomimetics Based on a Thiazolidine Moiety

Pietro      Campiglia; Isabel      Gomez-Monterrey; Alfonso      Carotenuto; Teresa      Lama; Maria   V.   Diurno; Alessia      Bertamino; Orazio      Mazzoni; Marina      Sala; Ettore      Novellino; Paolo      Grieco

doi:10.2174/157017806778341951

Abstract

A short and general synthesis for the preparation of two series of conformationally constrained building block has been elaborated starting from amino acids. The intrinsic tendency of the dipeptide mimetic scaffold to induce β-turn formation was evaluated by computer methods. The results indicate that the diastereomers with the (R) configuration at the C-2 have high propensity to the type II β-turn formation.

Keywords: Thiazolidine, beta-turn mimetic, amino aldehyde

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Letters in Organic Chemistry

Title: Design and Synthesis of Small Libraries of Peptidomimetics Based on a Thiazolidine Moiety

Volume: 3 Issue: 7

Author(s): Pietro Campiglia, Isabel Gomez-Monterrey, Alfonso Carotenuto, Teresa Lama, Maria V. Diurno, Alessia Bertamino, Orazio Mazzoni, Marina Sala, Ettore Novellino and Paolo Grieco

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Keywords: Thiazolidine, beta-turn mimetic, amino aldehyde

Abstract: A short and general synthesis for the preparation of two series of conformationally constrained building block has been elaborated starting from amino acids. The intrinsic tendency of the dipeptide mimetic scaffold to induce β-turn formation was evaluated by computer methods. The results indicate that the diastereomers with the (R) configuration at the C-2 have high propensity to the type II β-turn formation.

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Campiglia Pietro, Gomez-Monterrey Isabel, Carotenuto Alfonso, Lama Teresa, Diurno V. Maria, Bertamino Alessia, Mazzoni Orazio, Sala Marina, Novellino Ettore and Grieco Paolo, Design and Synthesis of Small Libraries of Peptidomimetics Based on a Thiazolidine Moiety, Letters in Organic Chemistry 2006; 3 (7) . https://dx.doi.org/10.2174/157017806778341951