77081-05-1Relevant academic research and scientific papers
Coenzyme Models. 28. Facile Oxidation of Alcohols and Amines by 3-Hydroxy-N-methylacridinium Ion, a New NAD+ Model Compound
Shinkai, Seiji,Hamada, Hisatake,Kuroda, Hideo,Manabe, Osamu
, p. 2333 - 2338 (1981)
The title compound (Ac+OH) was synthesized for the purpose of developing a new NAD+ model compound which is capable of oxidizing alcohols and amines.The absorption spectrum of Ac+OH was similar to that of N-methylacridinium ion (Ac+) in the acidic pH region and to that of 5-deazaflavin in the basic pH region.The absorption spectrum of the reduced form was analogous to that of 3-aminophenol.The reduced form which was prepared by NaBH4 reduction was promptly reoxidized by molecular oxygen.With the aid of potassium tert-butoxide, Ac+OH oxidized benzyl alcoholand cyclohexanol to the corresponding aldehyde and ketone in almost quantitative yields.In contrast, Ac+ was totally useless as an oxidant under the same reaction conditions.Benzylamine was oxidized by Ac+ to benzaldehyde in low yields (11-24percent).On the other hand, the oxidation by Ac+OH occurred in good yields (82-88percent).When the reaction was carried out under an oxygen stream, the yield calculated on the basis of Ac+OH was enhanced up to 1800-2200percent.The results indicate that Ac+OH acts as an effective turnover oxidizing agent and that the 3-hydroxyl group plays a crucial role in the redox reactions occurring on the acridinium nucleus.This is the first example of the facile oxidation of alcohols and amines which mimics the catalytic behavior of NAD+ coenzyme.
