[14C]acrylonitrile: preparation via a stable tosylate intermediate and quantitative reaction with amine residues in...

A simple, convenient synthetic procedure for [14C]acrylonitrile is described. Na14CN is used as the radioactive starting material. Small (milligram) amounts are converted to 3-[14C]Hydroxypropionitrile by a substitution reaction with 2-chloroethanol. 3-[14C]Hydroxypropionitrile is then tosylated, and the specific activity of this intermediate product is easily determined using its uv extinction coefficient and scintillation counting. [14C]Acrylonitrile is obtained rapidly on distillation by heating the tosylate in the presence of a high boiling tertiary amine base catalyst. The tosylate intermediate can be stored, in contrast to radioactive acrylonitrile, which is unstable. The reaction of acrylonitrile with lysine, hydroxylysine, and histidine residues in human Achilles tendon collagen, as well as chromatographic separation and identification of the carboxyethyl derivatives of these amino acids, is also described.