title: Activation of n-3 polyunsaturated fatty acids as oxime esters: a novel approach for their exclusive incorporation into the primary alcoholic positions of the glycerol moiety by lipase.
abstract: A novel approach has been developed for activating the highly bioactive long-chain n-3 polyunsaturated fatty acids EPA and DHA as oxime esters and incorporating them exclusively to the end-positions of glycerol and enantiopure 1-O-alkylglycerols. The Candida antarctica lipase B was observed to display a superb regioselectivity when using the acetoxime esters of EPA and DHA as acyldonors under mild condition to keep acyl-migration side-reaction under complete control. Regiopure 1,3-diacylglycerols, 1-O-alkyl-3-acyl-sn-glycerols and their antipodes possessing EPA and DHA were afforded in very high purity and yields.
authors: Science Institute, University of Iceland, Dunhaga 3, 107 Reykjavik, Iceland.
authors: Carlos D
authors: CD
authors: Magnusson
authors: Gudmundur G
authors: GG
authors: Haraldsson
mesh_terms: D000215:Acylation; D004075:Diglycerides / Q000138:chemical synthesis* / Q000737:chemistry; D004800:Enzymes, Immobilized / Q000737:chemistry*; D004952:Esters; D004987:Ethers; D015525:Fatty Acids, Omega-3 / Q000737:chemistry*; D005656:Fungal Proteins / Q000737:chemistry*; D008049:Lipase / Q000737:chemistry*; D015394:Molecular Structure; D050178:Monoglycerides / Q000138:chemical synthesis* / Q000737:chemistry; D010091:Oximes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004075:Diglycerides; D004800:Enzymes, Immobilized; D004952:Esters; D004987:Ethers; D015525:Fatty Acids, Omega-3; D005656:Fungal Proteins; D050178:Monoglycerides; D010091:Oximes; D008049:Lipase; C431349:lipase B, Candida antarctica