Premium
Synthesis of L‐glutamic acid stereospecifically labeled at C‐4 with deuterium
Author(s) -
Ducrocq Claire,
Maréchal Paulette DecottigniesLe,
Azerad Robert
Publication year - 1985
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580220109
Subject(s) - chemistry , reductive amination , glutamic acid , yield (engineering) , deuterium , amination , stereochemistry , stereospecificity , sodium , amino acid , organic chemistry , biochemistry , catalysis , materials science , physics , quantum mechanics , metallurgy
4‐[ 2 H 2 ]‐L‐glutamic acid was prepared in excellent yield by enzymatic reductive amination of 4‐[ 2 H 2 ]‐2‐ketoglutaric acid. The synthesis of stereospecifically deuterated (4 R) and (4 S)‐[4‐ 2 H 2 ]‐L‐glutamic acids from (2 RS, 4 S) and (2 RS, 4 R)‐4‐hydroxyglutamic acids, involving a reduction step by sodium cyanoborodeuteride, was shown to proceed with 75% inversion of configuration.