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Hypothetical mechanism for the reaction of a cysteine-thiol group at the active-site of ALDH-2 with a nitrate group of PETN explaining the role of the number of nitrate (–ONO2) groups in the organic nitrate for its bioactivation. Three or more nitrate groups create a positively charged (electrophilic) environment at the nitrogens which facilitates the nucleophilic attack of an ALDH-2 thiol group with subsequent formation of a thionitrate intermediate.
