Evaluation of Biodegradable Glucose Based Surfactants as a Promoting Medium for the Synthesis of Peptidomimetics with the Coumarin Scaffold

Abstract

Abstract6‐O‐Glucose‐4‐phenylbutyrate was used successfully as promoting aqueous reaction medium for the synthesis of fourteen different α‐acyloxy carboxamides with the biologically relevant coumarin scaffold. Two different one‐pot protocols; chemical and chemoenzymatic, based on the usage of biodegradable surfactants for the synthesis of target products were developed. The chemoenzymatic method consists of 3‐steps in which the first step is oxidation catalyzed by Trametes versicolor laccase/O2, followed by spontaneous condensation reaction, and finally multicomponent Passerini reaction. All transformations occurred at room temperature in the same reaction vials without isolation of the reaction intermediates. The influence of the reaction conditions including substrate structure on the reaction course was studied. The application of an aqueous solution of 6‐O‐glucose 4‐phenylbutyrate as the reaction medium had the pivotal impact of the reaction rate providing target α‐acyloxy carboxamides with the yields up to 65 %. Obtained peptidomimetics were characterized by UV‐VIS and fluorescence spectroscopy.