Synthesis of 2S-[2-2H]-kynurenine and use in kinetic isotope effect studies with kynureninase

Article abstract of DOI:10.1016/S0040-4020(97)10013-8

2S-[2-²H]-Kynurenine has been synthesised by two different routes. Diacetylation/racemisation of racemic kynurenine in deuterium oxide followed by acylase catalysed resolution provides the most direct method. The alternative is to prepare 2S-[2-²H]-tryptophan by a similar procedure and then convert this through to 2S-[2-²H]-kynurenine via ozonolysis. Preliminary results on measurements of the primary deuterium isotope effect, and solvent isotope effect, are described.