Synthesis of ethyl arachidonate-19,19,20,20-d4 and ethyl dihomo-gamma-linolenate-19,19,20,20-d4.
Ethyl 5,8,11,14-eicosatetraenoate-19,19,20,20-d4 and ethyl 8,11,14-eicosatrienoate-19,19,20,20-d4 were synthesized by Grignard coupling of the methanesulfonyl ester of 2,5-undecadiyn-1-ol-10,10,11,11-d4 with 5,8-nonadiynoic acid and 8-nonynoic acid, respectively. The coupled products upon Lindlar reduction, followed by the preparation of their ethyl esters, yielded deuteriated ethyl arachidonate and ethyl dihomo-gamma-linolenate, which were completely characterized by 13C and 1H nuclear magnetic resonance and mass spectral analysis.
Luthria
D L
DL
Department of Medical Biochemistry, Ohio State University, Columbus 43210.
Sprecher
H
H
D015126:8,11,14-Eicosatrienoic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D001095:Arachidonic Acids / Q000138:chemical synthesis*; D002849:Chromatography, Gas; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy
D001095:Arachidonic Acids; C035723:ethyl arachidonate; C012312:ethyl dihomo-gamma-linolenate; D015126:8,11,14-Eicosatrienoic Acid