American Chemical Society
ol062077j_si_001.pdf (2.65 MB)

Selective Reduction of Peptide Isothiazolidin-3-ones

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journal contribution
posted on 2006-12-07, 00:00 authored by Timothy P. Shiau, Daniel A. Erlanson, Eric M. Gordon
Isothiazolidinones 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.