A Model for Metabolic Activation of Dialkylnitrosoamines. Oxidative Dealkylation 2-(N-Nitrosoalkylamino)acetonitriles by a Flavin Mimic in Aqueous Solution

Article abstract of DOI:10.1021/jo00234a018

It is found for the first time that a flavin mimic, benzo<1,2-g:5,4-g'>dipteridine (BDP), reacts with 2-(N-nitrosoalkylamino)acetonitriles via oxidative dealkylation to yield the corresponding alcohols (ROH) and the 2-e-reduced BDP in aqueous acetonitrile.Kinetic studies reveal that the rates are first order with respect to and ->, respectively.Kinetic isotope effects (k_H/k_D) for RN(NO)CD2CN (R = Me, n-Bu, Ph, and PhCH2) are found to be 2.2-4.2, indicating that deprotonation is involved in the rate-determining step.The mechanism of the oxidative dealkylation of the nitrosoamines by the flavin mimic is discussed.