Journal article

Radical Formation in the Gas-Phase Ozonolysis of Deprotonated Cysteine

George N Khairallah, Alan T Maccarone, Huong T Pham, Timothy M Benton, Tony Ly, Gabriel da Silva, Stephen J Blanksby, Richard AJ O'Hair

Angewandte Chemie International Edition | WILEY-V C H VERLAG GMBH | Published : 2015

Abstract

Although the deleterious effects of ozone on the human respiratory system are well-known, many of the precise chemical mechanisms that both cause damage and afford protection in the pulmonary epithelial lining fluid are poorly understood. As a key first step to elucidating the intrinsic reactivity of ozone with proteins, its reactions with deprotonated cysteine [Cys-H](-) are examined in the gas phase. Reaction proceeds at near the collision limit to give a rich set of products including 1) sequential oxygen atom abstraction reactions to yield cysteine sulfenate, sulfinate and sulfonate anions, and significantly 2) sulfenate radical anions formed by ejection of a hydroperoxy radical. The fre..

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