A model for metabolic activation of dialkylnitrosamines. Oxidative dealkylation of 2-(N-nitrosoalkylamino) acetonitriles by a flavin mimic in aqueous solution

…, T Yokoyama, M Ikuta, K Yoshida

Index: Yano, Yumihiko; Yokoyama, Takeshi; Ikuta, Masato; Yoshida, Kitaro Journal of Organic Chemistry, 1987 , vol. 52, # 25 p. 5606 - 5610

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Citation Number: 12

Abstract

It is found for the first time that a flavin mimic, benzo [1, 2-g: 5, 4-gldipteridine (BDP), reacts with 2-(N-nitrosoalky1amino) acetonitriles [RN (NO) CH, CN] 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 [RN (NO) CH, CN] and [OH- ], respectively. Kinetic isotope effects (kH/kD) for RN (NO) CD2CN (R= Me, n-Bu, Ph, and ...