Premium
Chemoenzymatic synthesis of carbon‐14 labelled antioxidants
Author(s) -
Deigner H. P.,
Freyberg C.,
Heck R.
Publication year - 1993
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.2580330303
Subject(s) - chemistry , nitrilase , hydrolysis , cyanide , nucleophile , nitrile , organic chemistry , alkyl , chemical synthesis , aryl , combinatorial chemistry , catalysis , biochemistry , in vitro
The syntheses of [ 14 C] labelled antioxidants are described. We developed an efficient synthetic methodology to prepare a series of labelled amides with antioxidant activity, starting from [ 14 C] KCN and alkyl or aryl halides. By a combination of nucleophilic displacement of halides by [ 14 C] cyanide, mediated by ultrasound and subsequent mild and selective enzymatic hydrolysis of the resulting nitriles, labelled carboxylic acids were obtained. Labelled amines were prepared by reduction of the respective nitriles. Availability of [ 14 C] KCN, efficient introduction of the label by ultrasound mediated reaction and selective and mild hydrolysis by comercially available nitrilase (Rhodococcus sp.), makes possible a wide range of applications of this methodology in the synthesis of functionalized labelled compounds.