Synthesis of sulfate esters of phosphatidylglycerol (diphytanyl ether analog)

Synthesis of 1-sn-phosphatidyl-3′-sn-glycero-1′-sulfate (phosphatidylglycero-1-sulfate) was achieved by monosulfation of 1-sn-phosphatidyl-3′-sn-glycerol (diphytanyl ether analog) with an equimolar amount of SO3–pyridine complex at room temperature; with excess sulfation reagent at 60°C, the 1′,2′-disulfate ester was obtained. The phosphatidylglycero-2-sulfate isomer was synthesized by an unambiguous route starting from the bacterial 2,3-di-O-phytanyl-sn-glycerol. The synthetic phosphatidylglycerosulfates were characterized by analytical, chromatographic, optical rotatory, and spectral (infrared and NMR) data and compared with the phosphatidylglycerosulfate isolated from Halobacterium cutirubrum.

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