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Synthesis of (2R)‐ and (2S)‐[3‐ 2 H]‐valine
Author(s) -
Easton Christopher J.,
Findlay Nicola G.
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.2580220705
Subject(s) - chemistry , valine , labelling , hydrolysis , walden inversion , chloride , stereochemistry , medicinal chemistry , radiochemistry , organic chemistry , amino acid , biochemistry
(2R)‐Valine and the (2S)‐isomer were esterified and bezoylated. The derivatives were chlorinated at C‐3 by treatment with sulphuryl chloride, reduced to the 3‐ 2 H derivatives by reaction with triphenyltin deuteride, then hydrolysed to give (2R)‐ and (2S)‐[3‐ 2 H]‐valine. The labelling is achieved with complete retention of optical purity.