Amino acid fluorides: viable tools for synthesis of peptides, peptidomimetics and enantiopure heterocycles

Abstract

This review provides a broad perspective of the uses of amino acid fluorides in the synthesis of peptides and a wide range of other molecules. The topic is discussed with reference to the preparation of N-protected amino acid fluorides, their reactivity, coupling and their synthetic applications. The merits of the use of amino acid fluorides as coupling agents for making difficult peptides and in combating the problem of stereomutation, as well as their successful use in solid phase peptide synthesis, are reported with examples. Recent developments in the application of amino acid fluorides for making amino acid derivatives, peptide conjugates, peptide mimics and heterocycles are also reviewed.