Synthesis of polyunsaturated beta-thia and gamma-thia fatty acids from naturally derived polyunsaturated fatty alcohols and in vitro evaluation of their susceptibility to beta-oxidation

A range of polyunsaturated β- and γ-thia fatty acids are conveniently prepared in two steps from naturally derived polyunsaturated fatty alcohols. In vitro β-oxidation studies using acyl Co-A oxidase from Arthrobacter species indicate that (all-Z)-(eicosa-5,8,11,14-tetraenyloxy) acid, synthesised as reported earlier, (all-Z)-(eicosa-5,8,11,14-tetraenylthio)acetic acid and (all-Z)-(eicosa-5,8,11,14-tetraenylthio)succinic acid are not susceptible to oxidation, whereas 3-[(all-Z)-(eicosa-5,8,11,14-tetraenylthio)]propionic acid is oxidised with V(O) approximately 40% of that of arachidonic acid. In competitive experiments, none of these novel polyunsaturated fatty acids effect the β-oxidation of arachidonic acid.Michael J Pitt, Christopher J Easton, Antonio Ferrante, Alfred Poulos, Deborah A Rathje