Synthesis of unsaturated carnitine esters with N-acyl imidazoles.
A novel procedure is described for the synthesis of acylcarnitines. This entails the synthesis of an N-acyl imidazole intermediate, which subsequently is reacted with L-carnitine perchlorate to form the acylcarnitine. The procedure is rapid and simple, and does not require a large excess of N-acyl imidazole to achieve a reaction yield of 50-70%. A procedure, based on reverse-phase Sep-Pak cartridges for rapid isolation of acylcarnitines from these reaction mixtures is also described. These procedures have, in particular, been applied in the synthesis of polyunsaturated acylcarnitines, including docosahexaenoylcarnitine.
D000215:Acylation; D002331:Carnitine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D055598:Chemical Phenomena; D002621:Chemistry; D007093:Imidazoles; D013997:Time Factors
D007093:Imidazoles; D002331:Carnitine