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Simple and efficient preparation of (R)‐ and (S)‐enantiomers of α‐carbon deuterium‐labelled α‐amino acids
Author(s) -
Mitulovi Goran,
Lämmerhofer Michael,
Maier N. M.,
Lindner Wolfgang
Publication year - 2000
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/(sici)1099-1344(200004)43:5<449::aid-jlcr331>3.0.co;2-0
Subject(s) - racemization , chemistry , enantiomer , amino acid , acetic acid , deuterium , racemic mixture , solvent , organic chemistry , enantiomeric excess , enantioselective synthesis , catalysis , biochemistry , physics , quantum mechanics
A procedure for the synthesis of (R)‐ and (S)‐enantiomers of α‐carbon deuterium‐labelled α‐amino acids, exemplified for (R)‐ and (S)‐[2‐ 2 H 1 ]‐Leu is described. Starting from the respective (S)‐ or (R)‐enantiomer or from the racemic mixture of an α‐amino acid the selective proton exchange at the α‐carbon is carried out by racemization via a Schiff base in monodeuterated acetic acid as solvent which serves as deuterium source. After N‐protection the racemic mixture is liquid chromatographically separated into the individual (R)‐ and (S)‐enantiomers on preparative scale employing a chiral anion exchanger based on carbamoylated quinine as chiral selector. After deprotection the enantiomerically pure products can be obtained in good yields. Copyright © 2000 John Wiley & Sons, Ltd.