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

Carl S Rye, Jonathan Bayldon Baell, Ian Philip Street

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8 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)3306 - 3311
Number of pages6
JournalTetrahedron
Volume63
Issue number16
DOIs
Publication statusPublished - 2007
Externally publishedYes

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