Lanthionine cleavage

Scheme 11 Synthesis of a Lanthionine Peptide via Solid-Phase Peptide Synthesis and Final Cleavage from Kaiser Oxime Resin 481...

The formation of dehydroalanine would also increase the likelihood of lanthionine formation which would be resistant to peptide bond cleavage. It is likely that dehydroalanine formation itself is responsible for the final peptide bond cleavage through migration of the double bond and subsequent hydrolysis. 

As mentioned before, hydrolytic cleavage of peptide bonds in keratins, as well as formation of lanthionyl residues, can also occur in alkali. In addition to lanthionine, lysinoalanine [59] and beta-aminoalanine [60] residues can be formed in some keratins under alkaline conditions. 

The resistance to proteolytic cleavage that is conferred by the lanthionine rings may ultimately prove very important to the utility of lantibiotics and lantibitaic analogs for pharmacological purposes. Important barriers to the use of peptides for treatment of internal infections as well as external ones are the potential for allergic reactions to the... 

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