ol062077j_si_001.pdf (2.65 MB)
Selective Reduction of Peptide Isothiazolidin-3-ones
journal contribution
posted on 2006-12-07, 00:00 authored by Timothy P. Shiau, Daniel A. Erlanson, Eric M. GordonIsothiazolidinones are a rare but potentially important chemical moiety in biochemistry. We report the identification of several thiol, phosphinate,
and carbon nucleophiles that form covalent adducts by addition to the sulfenamide sulfur. This reduction is selective for isothiazolidinones
over similar peptide disulfides. We synthesized a coumarin-based thioacid nucleophile which shows a marked fluorescence increase after
addition to an isothiazolidinone sulfenamide bond.