The enzymic conversion of 13-hydroperoxylinoleic acid into 13-hydroxy-12-oxooctadec-9(Z)-enoic acid and 9-hydroxy-12-oxooctadec-10(E)-enoic acid: isotopic evidence for an allene epoxide intermediate

Abstract

Using synthetic [9,10,12,13-²H₄]linoleic acid as substrate it is shown that flax enzyme preparation forms [9,10,13-²H₃]-13-hydroxy-12-oxooctadec-9(Z)-enoic acid and [9,10,13-²H₃]-9-hydroxy-12oxooctadec-10(E)-enoic acid with loss of the deuterium originally at C-12, thus demonstrating that an allene epoxide is involved as an intermediate and that transfer of deuterium from C-12 to C-11 does not occur.