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

• Published in: Chemistry and physics of lipids Vol. 92; no. 1; pp. 63 - 69
• Main Authors: Pitt, Michael J, Easton, Christopher J, Ferrante, Antonio, Poulos, Alfred, Rathjen, Deborah A
• Format: Journal Article
• Language: English
• Published: Elsevier Ireland Ltd 01.03.1998
• Subjects: Polyunsaturated fatty acids; Synthesis; Thioethers; β-Oxidation; Synthesis; Polyunsaturated fatty acids; Thioethers; β-Oxidation
• ISSN: 0009-3084; 1873-2941
• DOI: 10.1016/S0009-3084(98)00002-4

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)acetic 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 0 appproximately 40% of that of arachidonic acid. In competitive experiments, none of these novel polyunsaturated fatty acids effect the β-oxidation of arachidonic acid.