Preparation of 2-aminomuconate from 2-aminophenol by coupled enzymatic dioxygenation and dehydrogenation reactions

Abstract

2-Aminomuconate is an intermediate in the oxidative metabolism of tryptophan in mammals. The compound is not commercially available, and studies of its metabolism have been prevented by the lack of a chemical synthesis and the instability of the molecule. We report here the formation of 2-aminomuconate from 2-aminophenol by the coupled action of 2-aminophenol 1,6-dioxygenase and 2-aminomuconic semialdehyde dehydrogenase from Pseudomonas pseudoalcaligenes JS45, and isolation of the product by anion exchange chromatography. The overall procedure was completed within 3 h with a yield of 62%. The availability of the dicarboxyl α-amino acid provides the basis for investigation of the physiological function of 2-aminomuconate in the neuropathologically significant oxidative metabolism of tryptophan.