Cyclization step of noradrenaline and adrenaline autoxidation: a quantum chemical study
Nejc Umek
Abstract
-quinone species, one with an unprotonated and one with a protonated quinone group can participate in the cyclization reaction and that the mechanisms of these reactions significantly differ, emphasizing the importance of quinone group protonation states in the reaction mechanism. With a thorough exploration of the reaction kinetics, we further showed that at acidic pH the cyclization reaction rate is pH independent, while at alkaline pH the pH dependence is marked, explaining the experimentally observed complex pH dependence.
Topics & Concepts
AutoxidationChemistryProtonationQuinoneCatecholaminePhotochemistryReaction rate constantIntramolecular forceReaction mechanismLimitingKineticsMedicinal chemistryStereochemistryOrganic chemistryCatalysisEngineeringMedicineQuantum mechanicsIonPhysicsInternal medicineMechanical engineeringFree Radicals and AntioxidantsElectrochemical Analysis and ApplicationsPhotoreceptor and optogenetics research