Pyridoxal Methochloride Catalysis of the β-Elimination Reaction of Methyl 3-Chloroalaninate in Water

Article abstract of DOI:10.1246/bcsj.57.1031

The β-elimination reaction of methyl 3-chloroalaninate has been investigated in the absence and presence of pyridoxal methochloride (2) or pyridoxal (3).Apparently, compound 2 was about twice as effective as 3 in the catalytic reaction that proceeds via a Schiff base of substrate and 2 or 3.The pH-rate profiles for the catalytic reaction with 2 and 3 were analyzed in terms of ionization of the various Schiff base species present in solution.It was found that the reactivity of the Schiff base decreases as the ionization of the molecule progresses.The reaction mechanism and its relevance to the catalysis of pyridoxal phosphate-dependent enzymes are discussed.