Synthesis of Stereospecifically Deuterated Phenylalanines and Determination of Their Configuration
Open Access
- 1 January 1977
- journal article
- research article
- Published by Wiley in European Journal of Biochemistry
- Vol. 72 (2) , 247-250
- https://doi.org/10.1111/j.1432-1033.1977.tb11246.x
Abstract
Starting from trans‐cinnamic acid a chiral (−)3‐phenyl‐[2,3‐2H]propionic acid has been synthesized using Clostridium kluyveri cells as catalyst. The chiral dideuterated acid has been converted by chemical methods to a mixture of (2R) and (2S)‐phenyl[2,3‐2H]‐alanine. By means of 1H nuclear magnetic resonance spectroscopy and the action of D and L‐amino‐acid oxidase the configuration of the phenylalanine has been shown to be (2R, 3S) and (2S, 3S), respectively. The labelled phenylalanine is thus sterically and isotopically homogeneous at position 3 but heterogeneous at position 2.This publication has 11 references indexed in Scilit:
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