title: The preparation of 2-O-[1'-C]arachidonoyl-1-O-stearoyl-sn-glycerol.
abstract: 2-O-Arachidonoyl-1-O-stearoyl-sn-glycerol is the most abundant molecular species of the 1,2-diacyl-sn-glycerol signaling lipids in neural tissue. The facile preparation of 2-O-[1'-(14)C]arachidonoyl-1-O-stearoyl-sn-glycerol from 2-O-[1'-(14)C]arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine at a hexane and phosphate buffer interface with phospholipase C was demonstrated on a 20 µCi scale in 83% radiochemical yield. The specific activity of the product 2-O-[1'-(14)C]arachidonoyl-1-O-stearoyl-sn-glycerol was 57.0 mCi/mmol and the radiochemical purity was determined to be >99% by TLC. The hydrolysis of this lipid biosynthetic intermediate with lipoprotein lipase was shown to produce 2-O-[1'-(14)C]arachidonoylglycerol (2-AG). The (14)C-radiolabeled monoacylglycerol 2-AG is an endogenous cannabinoid receptor-signaling molecule (endocannabinoid).
authors.affiliation: Center for Drug Discovery, Northeastern University, 360 Huntington Avenue, 116 Mugar Life Sciences Building, Boston, MA 02115, USA.
authors.forename: Richard I
authors.initials: RI
authors.lastname: Duclos
authors.forename: S John
authors.initials: SJ
authors.lastname: Gatley
authors.forename: Shachi R
authors.initials: SR
authors.lastname: Bhatt
authors.forename: Meghan
authors.initials: M
authors.lastname: Johnston