The chiral synthesis and biochemical properties of electron rich phenolic sulfoxide analogs of sparsomycin.

A novel route to activated phenolic sulfoxide analogs of sparsomycin has been developed. These analogs display an enhanced "preincubation effect" as inhibitors of peptide-bond formation. This time-dependent component of inhibition, which is postulated to result from an enzyme-mediated Pummerer rearrangement, is the dominant route to inhibition in these activated analogs.