Synthesis of sulfate esters of phosphatidylglycerol (diphytanyl ether analog)

• Main Authors: A.J. Hancock, M. Kates
• Format: Article
• Language: English
• Published: Elsevier 1973-07-01
• Series: Journal of Lipid Research
• Subjects: phosphosulfolipid; halophilic bacteria; 1-sn-phosphatidyl-3′-sn-glycero-1′-sulfate; 1-sn-phosphatidyl-1′-sn-glycero-2′-sulfate; 1-sn-phosphatidyl-3′-sn-glycero-1′,2′-disulfate; 2-O-myristoyl-3-O-benzyl-sn-glycerol
• Online Access: http://www.sciencedirect.com/science/article/pii/S0022227520368760

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.