The total synthesis of 2-O-arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine-1,3,1'-(13)C3 and -2,1'-(13)C2 by a novel chemoenzymatic method.
2-O-Arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine was synthesized with carbon-13 enrichment of the three glycerol carbons and the carbonyl of the stearoyl group. Phospholipase A(2) was utilized to give optically pure lyso-PC, and only 3% acyl migration occurred during reacylation with arachidonic acid anhydride. This phospholipid is an important biosynthetic precursor of arachidonic acid metabolites as well as the endocannabinoid 2-arachidonoylglycerol (2-AG), and is now available for NMR studies.
Duclos
Richard I
RI
Center for Drug Discovery, Northeastern University, 116 Mugar Life Sciences Building, 360 Huntington Avenue, Boston, MA 02115, USA. duclos@neu.edu
D016718:Arachidonic Acid / Q000378:metabolism; D001095:Arachidonic Acids / Q000378:metabolism; D002247:Carbon Isotopes / Q000737:chemistry; D063388:Endocannabinoids; D005989:Glycerides / Q000378:metabolism; D007553:Isotope Labeling / Q000379:methods; D009682:Magnetic Resonance Spectroscopy; D010713:Phosphatidylcholines / Q000138:chemical synthesis* / Q000737:chemistry; D010741:Phospholipases A / Q000378:metabolism
D001095:Arachidonic Acids; D002247:Carbon Isotopes; D063388:Endocannabinoids; D005989:Glycerides; D010713:Phosphatidylcholines; C043644:1-stearoyl-2-arachidonylphosphatidylcholine; D016718:Arachidonic Acid; C094503:glyceryl 2-arachidonate; D010741:Phospholipases A
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