Alkylidene acetoacetamides are useful building blocks for the preparation of a number of biologically active derivatives, including dehydro-β-amino-acid-containing peptidomimetics. A one-pot two-step protocol for the preparation of amino-acid-derived unsaturated acetoacetamides has been optimized. The use of microwave activation avoids, or at least decreases, the need for catalysts in both steps. A leucine derivative was selected from the small collection of molecules obtained to be transformed into the corresponding dehydro-β-amino-acid-containing peptidomimetic. It is known that such fragments are able to induce β-turns into peptide sequences, and, due to the presence of the unsaturation, they may represent sites for selective modification and conjugation.

One-Pot Two-Step Microwave-Assisted Synthesis of Alkylidene Acetoacetamido Esters, Useful Intermediates for β-Dehydropeptides

VIOLA, ANGELO;FERRAZZANO, LUCIA;GRECO, ROBERTO;CERISOLI, LUCIA;TOLOMELLI, ALESSANDRA
2016

Abstract

Alkylidene acetoacetamides are useful building blocks for the preparation of a number of biologically active derivatives, including dehydro-β-amino-acid-containing peptidomimetics. A one-pot two-step protocol for the preparation of amino-acid-derived unsaturated acetoacetamides has been optimized. The use of microwave activation avoids, or at least decreases, the need for catalysts in both steps. A leucine derivative was selected from the small collection of molecules obtained to be transformed into the corresponding dehydro-β-amino-acid-containing peptidomimetic. It is known that such fragments are able to induce β-turns into peptide sequences, and, due to the presence of the unsaturation, they may represent sites for selective modification and conjugation.
Viola, Angelo; Ferrazzano, Lucia; Greco, Roberto; Cerisoli, Lucia; Caldi, Jonathan; Tolomelli, Alessandra
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/566051
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