Solid-Phase Synthesis and Cyclative Cleavage of Quorum Sensing ­Depsipeptide Analogues by Acylphenyldiazene Activation

Depsipeptide analogues of auto-inducing peptides (AIPs) from all four Staphylococcus aureus subgroups were prepared as panning reagents for in vitro antibody selection. Stepwise Fmoc solid-phase synthesis was used to prepare the linear precursors, which were cyclized without epimerization in a one-pot cleavage reaction following oxidation of the stable acylphenylhydrazine linkage to the reactive acylphenyldiazene.