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 SO(3)-pyridine complex at room temperature; with excess sulfation reagent at 60 degrees C, the 1',2'-disulfate ester was obtained. The phosphatidyl-glycero-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.
D002855:Chromatography, Thin Layer; D003903:Deuterium; D006217:Halobacterium; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D009904:Optical Rotation; D010743:Phospholipids / Q000138:chemical synthesis*; D010759:Phosphorus Isotopes; D013055:Spectrophotometry, Infrared; D013464:Sulfuric Acids / Q000138:chemical synthesis*
D010743:Phospholipids; D010759:Phosphorus Isotopes; D013464:Sulfuric Acids; D003903:Deuterium