An efficient and novel method for the synthesis of cardiolipin and its analogs.
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.
Lin
Zhen
Z
NeoPharm, Inc., Waukegan, Illinois 60085, USA.
Ahmad
Moghis U
MU
Ali
Shoukath M
SM
Ahmad
Imran
I
D002308:Cardiolipins / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods; D015394:Molecular Structure
D002308:Cardiolipins