Synthesis, reactivity and applications of 1-fluoroalkyl carboxylates: novel synthetic substrates for esterases and lipases

A series of 1-fluoroalkyl carboxylate derivatives was synthesised by reacting a carboxylic acid and a ketone or aldehyde with (diethylamino)sulfur trifluoride (DAST). The reactivity of these compounds towards the nucleophiles benzylamine and water was investigated. The hydrolysis of the 1-fluoroalkyl carboxylates by an esterase was observed, along with the concomitant release of the fluoride ion, demonstrating the potential for a new esterase assay platform. Other applications may include a detectable in situ inhibitor synthesis protocol.