Enantioselective separation of some polyunsaturated epoxy fatty acids by high-performance liquid chromatography on a cellulose phenylcarbamate (Chiralcel OC) stationary phase.
cis-Epoxides of linoleic acid, alpha-linolenic acid, arachidonic acid and the omega 3-epoxide of eicosapentaenoic acid were chromatographed on a cellulose trisphenylcarbamate (Chiralcel OC) stationary phase in the normal-phase mode. The R,S and S,R enantiomers of methyl-14(15)epoxyeicosatrienoate, methyl-9(10)epoxyoctadecadienoate and methyl-9(10)epoxyoctadecenoate could be partly resolved. The R,S enantiomer of methyl-14(15)epoxyeicosatrienoate eluted before the S,R enantiomer. [14C]14(15)Epoxyeicosatrienoic acid was isolated from an incubation of [14C]20:4n-6 with microsomes of rabbit kidney cortex and the S,R enantiomer was found to predominate (about 2:1).
Oliw
E H
EH
Department of Pharmaceutical Pharmacology, Uppsala University Biomedical Centre, Sweden.
D000818:Animals; D002219:Carbamates; D002482:Cellulose; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D004852:Epoxy Compounds / Q000032:analysis*; D005231:Fatty Acids, Unsaturated / Q000032:analysis* / Q000737:chemistry; D007672:Kidney Cortex / Q000737:chemistry; D008297:Male; D048448:Phenylcarbamates; D011817:Rabbits; D013237:Stereoisomerism
D002219:Carbamates; D004852:Epoxy Compounds; D005231:Fatty Acids, Unsaturated; D048448:Phenylcarbamates; C079151:cellulose trisphenylcarbamate; D002482:Cellulose