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E N D Presentation Transcript The biological chemistry of thiols: reactions with biologically-relevant oxidants reactions of radicals formed on oxidation Peter Wardman University of Oxford, Gray Cancer Institute Supported by Overview • Thiol oxidation products & reactivity of oxidants • thiol ionization a key property: pH-sensitive chemistry • non-enzyme-based oxidants are mainly radicals • enzyme-based oxidants utilize H2O2 cofactor • Thiyl radical is a key precursor of products • a moderately strong oxidant in its own right • Addition/transformation routes of thiyl radicals • conjugation with thiolate constitutes a ‘redox switch’ • isomerization of cis fatty acids to trans • intramolecular transformation of GSH thiyl radicals Biologically-important thiols Adult human has ~ 30 g glutathione (typical cytosolic concentration is 5–10 mM) • Cysteine is the most abundant thiol moiety • Glutathione is a cysteinyl peptide and the most abundant non-protein thiol • Lipoate is an example of a dithiol, can reduce GSH Thiol ionization (dissociation of S–H):the most important single property

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