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Total synthesis and biological activity of the lantibiotics
The lantibiotics are an important class of antibiotic peptides with complex bridged structures formed by a series of thioether links between the amino acid side chains. In spite of the pressing need for new classes of antibiotics for use against resistant bacteria, these have been little explored because of the difficulties inherent in their synthesis. We have developed a new, direct route to the parent amino acid, lanthionine, which avoids problems encountered in previous approaches. We have then developed a new method for synthesising lantibiotics using solid-phase peptide synthesis techniquesWe are using this approach to prepare peptides with multiple thioether bridges, and even with overlapping thioether bridges. We are currently applying this to the synthesis of subunits of nisin, and investigating how the sequence of each subunit of nisin affects the conformation of the ring and the binding of nisin to the biological targets.
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