Abstract
Synthesis and a study of the 13C NMR spectroscopic properties of positional isomers of some C18 acetylenic thia fatty esters
Highlights
Unsaturated thia fatty acids, such as 13-thia-9Z,11E-octadecadienoic acid and 13-thia-9E,11Eoctadecadienoic acid are found to be reversible competitive inhibitors of lipoxygenase.[1,2,3,4,5] Corey et al.[6,7] reported that the 7-thia, 10-thia- and 13-thia-arachidonic acids are potent inhibitors in leukotriene biosynthesis
We describe the synthesis of a set of positional isomers of C18 acetylenic thia fatty esters (5-8, Scheme 1) in an effort to study the effect of the sulfur atom on the chemical shifts of the carbon nuclei in the alkynyl chain of these thia fatty ester isomers by nuclear magnetic resonance spectroscopy
The 13C nuclear magnetic resonance (NMR) chemical shifts of carbon nuclei are very susceptible to changes in the positions of the functional groups on the alkyl chains of fatty acids, making this analytical technique a much more informative one than 1H NMR, especially in the confirmation of the structure of closely related fatty ester isomers
Summary
Unsaturated thia fatty acids, such as 13-thia-9Z,11E-octadecadienoic acid and 13-thia-9E,11Eoctadecadienoic acid are found to be reversible competitive inhibitors of lipoxygenase.[1,2,3,4,5] Corey et al.[6,7] reported that the 7-thia-, 10-thia- and 13-thia-arachidonic acids are potent inhibitors in leukotriene (lipoxin) biosynthesis. We have used the same base values employed for an unperturbed carbon nucleus of a methylene group as reported by Bus et al.[16] and the shift for a methyl and the carbonyl atom of the methyl ester group as 29.75, 14.10 and 174.35 ppm, respectively.
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