Synthesis of stereospecifically deuterated phenylalamines and determination of their configuration.
1. Starting from trans-cinnamic acid a chiral (-)3-phenyl-[2,3-2H]propionic acid has been synthesized using Clostridium kiuyveri cells as catalyst. 2. The chiral dideuterated acid has been converted by chemical methods to a mixture of (2R) and (2S)-phenyl[2,3-2H]-alanine. 3. By means of 1H nuclear magnetic resonance spectroscopy and the action of D and L-amino acid oxidase the configuration of the phenylalamine has been shown to be (2R, 3S) and (2S, 3S), respectively. The labelled phenylalanine is thus sterically and isotopically homogenous at position 3 but heterogenous at position 2.
D000594:Amino Acid Oxidoreductases / Q000378:metabolism; D002934:Cinnamates; D003605:D-Amino-Acid Oxidase / Q000378:metabolism; D003903:Deuterium; D005583:Fourier Analysis; D007553:Isotope Labeling; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010649:Phenylalanine / Q000138:chemical synthesis; D011422:Propionates; D013237:Stereoisomerism
D002934:Cinnamates; D011422:Propionates; D010649:Phenylalanine; D003903:Deuterium; D000594:Amino Acid Oxidoreductases; D003605:D-Amino-Acid Oxidase