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

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, synthe...

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Bibliographic Details
Published in:Chemistry and physics of lipids 1998-03, Vol.92 (1), p.63-69
Main Authors: Pitt, Michael J, Easton, Christopher J, Ferrante, Antonio, Poulos, Alfred, Rathjen, Deborah A
Format: Article
Language:English
Subjects:
Polyunsaturated fatty acids
Synthesis
Thioethers
β-Oxidation
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Summary: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.
ISSN:0009-3084
1873-2941
DOI:10.1016/S0009-3084(98)00002-4