Coenzyme model studies. Part 3. Transimination and reduction using NADH models

Abstract

N-Arylidenealkylamines (1) undergo transimination with aniline derivatives in glacial acetic acid. In the presence of 3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine (Hantzsch ester) transimination is followed by reduction of the transimination products (3) but not of (1). Transimination also takes place in acetonitrile on treatment of the amines (1) with anilinium trifluoroacetate. These phenomena are analogous to transiminations at the catalytic sites of pyridoxal-dependent enzymes and a similar transimination is followed by reduction in the mechanism of glutamate dehydrogenase.