An efficient and novel method for the synthesis of cardiolipin and its analogs

Lipids
Zhen LinImran Ahmad

Abstract

A novel synthetic method has been developed for cardiolipin and its analog via a chlorophosphoramidite coupling reaction followed by oxidation. The reagent, N,N-diisopropylmethylphosphoramidic chloride, couples effectively with 1,2-O-dimyristoyl-sn-glycerol in the presence of an amidite activator to form a phosphoamidite intermediate, which then reacts with 2-O-benzylglycerol in the presence of a basic catalyst followed by in situ oxidation to give the corresponding protected cardiolipin. Deprotection of the protecting groups provides tetramyristoyl cardiolipin in good overall yield of 60%. The synthetic method is applicable to large-scale synthesis of cardiolipin and various analogs with or without unsaturation for liposomal drug delivery.

References

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Jan 1, 1968·Chemical & Pharmaceutical Bulletin·K Inoue, S Nojima
Aug 20, 1966·Journal of the American Chemical Society·R M Saunders, H P Schwarz
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