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An efficient and novel method for the synthesis of cardiolipin and its analogs
Author(s) -
Lin Zhen,
Ahmad Moghis U.,
Ali Shoukath M.,
Ahmad Imran
Publication year - 2004
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-004-1231-5
Subject(s) - cardiolipin , cardiolipins , chemistry , reagent , combinatorial chemistry , degree of unsaturation , catalysis , yield (engineering) , glycerol , bioorganic chemistry , organic chemistry , biochemistry , membrane , phospholipid , materials science , enzyme , metallurgy
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.