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Whilst developing a strategy for the solid-phase synthesis of lanthionine-containing peptides, we became aware of some problems with a previously published route for the synthesis of orthogonally-protected lanthionine. We report a structural reassignment of the key iodoalanine intermediate and resulting lanthionine derivatives.

We report a new approach to the on-resin synthesis of cyclic peptides containing unnatural thioether side-chain bridges. An orthogonally protected nor-lanthionine was incorporated in a linear precursor peptide via stepwise solid-phase synthesis. This was followed by double allyl deprotection, cyclisation using PyAOP and subsequent chain-extension to give an analogue of ring C of nisin.