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Journal of Lipid Research, Vol. 43, 1150-1154, July 2002
Copyright © 2002 by Lipid Research, Inc.

Methods

JulyNonenzymatic synthesis of glycerolipids catalyzed by imidazole

Eric Testet^1,*, Malika Akermoun^*, Miyuki Shimoji, Claude Cassagne^* and Jean-Jacques Bessoule^*

^* UMR 5544/ESTBB, CNRS-Université Victor Segalen Bordeaux 2, 146 rue Léo Saignat, 33076 Bordeaux Cedex, France
Institute of Environmental Medicine, Division of Biochemical Toxicology, Karolinska Institute, Box 210, S-17177, Stockholm, Sweden

¹ To whom correspondence should be addressed. e-mail: eric.testet{at}estbb.u-bordeaux2.fr

Imidazole catalyzed acylations of lysolipids by acyl-CoAs in water at room temperature and at a pH close to neutrality. In the presence of oleoyl-CoA and either lysophosphatidylcholine, 1-palmitoyl-sn-glycero-3-phosphocholine (LPC); lysophosphatidylglycerol, monoacyl-sn-glycero-3-phosphoglycerol; lysophosphatidyl acid, 1-oleoyl-sn-glycero-3-phosphate; lysophosphatidylserine, monoacyl-sn-glycero-3-phosphoserin; or lysophosphatidylethanolamine, monoacyl-sn-glycero-3-phosphoethanolamine, the corresponding phospholipids were synthesized. Similarly, the use of lyso-platelet activating factor, an ether analog of LPC, yielded the formation of 1-O-alkyl-2-oleoyl-sn-glycero-3-phosphocholine. In the presence of LPC, an imidazole-catalyzed synthesis of phosphatidylcholine (PC) occurred when medium, long, and very long chain acyl-CoAs were added. With hydroxyacyl-CoA, a similar PC synthesis was obtained.

The process described in the present paper appears to offer several potential applications of interest for the synthesis of glycerophospholipids and triglycerides with labeled and/or an unusual or fragile fatty acid, or when suitable acyltransferases have not yet been described in the literature and/or are not commercially available. The method described is very safe and simple since lipids can be synthesized in tubes containing 0.7% imidazole in water, and left for a few hours at room temperature on the bench.

Abbreviations: C16-OH, omega-hydroxypalmitic acid; LPA, lysophosphatidyl acid, 1-oleoyl-sn-glycero-3-phosphate; LPAF, lyso-platelet activating factor, 1-O-alkyl-sn-glycero-3-phosphocholine; LPC, lysophosphatidylcholine, 1-palmitoyl-sn-glycero-3-phosphocholine; LPE, lysophosphatidylethanolamine, monoacyl-sn-glycero-3-phosphoethanolamine; LPG, lysophosphatidylglycerol, monoacyl-sn-glycero-3-phosphoglycerol; LPS, lysophosphatidylserine, monoacyl-sn-glycero-3-phosphoserine; NAPE, N-acyl phosphatidylethanolamine, diacyl-sn-glycero-3-phospho [N-octadecenoyl]-ethanolamine; PA, phosphatidic acid; PC, phosphatidylcholine; PE, phosphatidylethanolamine; PG, phosphatidylglycerol; PS, phosphatidylserine

Supplementary key words acyl-CoA • lysolipid • acylation • chemical method • omega hydroxypalmitoyl-CoA

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