Regioselective Solid-Phase Synthesis of Peptide Analogues Containing 3,4- or 3,5-Disubstituted Isoxazole as s-cis or s-trans Peptide Bond Mimics

摘要

A method for regioselective solid-phase synthesis of disubstituted peptidoisoxazoles is reported. Improved conditions for the synthesis of 3,5-disubstituted isoxazoles (mimicking s-trans peptide bond) without metal catalysts were implemented. New conditions enabling the synthesis of 3,4-disubstituted isoxazoles (mimicking s-cis peptide bond) using ruthenium catalysts were developed. This study provides a means for the regioselective preparation of new libraries of peptidomimetic molecules containing an isoxazole moiety within the backbone.