NMR chemical shift reagents in structural determination of lipid derivatives: IV. Methylcis- andtrans-9,10-epoxystearate and methylerythro- andthreo-9,10-dihydroxystearate

Chemical shift reagents were used to expand the amount of structural information obtainable from NMR studies of derivatives of methyl oleate and elaidate:methylcis-9,10-epoxystearate, methyltrans-9,10-epoxystearate, methyl erythro-9,10-dihydroxystearate, and methyl threo-9,10-dihydroxystearate. Chemical shift reagent studies of methyltrans-9,10-epoxystearate and methyl threo-9,10-dihydroxystearate afforded the most information. Chemical shift reagent studies of methylcis-9,10-epoxystearate and methyl erythro-9,10-dihydroxystearate were decidedly inferior. The series of complementary interpretive techniques previously developed during chemical shift reagent studies of monofunctional fatty esters and model polyfunctional fatty esters were found to be applicable in the current study. However, to avoid ambiguity in several proton assignments, supplementary spin decoupling experiments were necessary.