Synthesis of lantibiotic based templates for solid phase synthesis and combinatorial chemistry

Abstract

In an attempt to strive for environmental supremacy, many organisms biosynthesise and secrete peptide antibiotics which display activity against a variety of competitors. One such class of compounds is the lantibiotics, which are characterised by their unusually high proportion of non-proteinogenic residues, including the bridged amino acid lantionine. These novel residues essentially govern the structure and function of these exciting peptides. It is our wish to exploit the medicinally relevant properties of the lantibiotics by ultimately using lanthionyl scaffolds to support combinatorial libraries.

We describe a variety of approaches to the lantionine skeleton, and in particular focus our synthetic effort upon the idolanines. A stereoselective synthesis of lanthionines is presented, and the optical course of the reaction investigated by the method of Mosher. Finally, we apply our methodology to the synthesis of lanthionines suitable for solid phase applications, and demonstrate the utility of our approach by synthesising a lanthionyl peptide on a solid support.

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