Journal of Lipid Research, Vol. 14, 430-437, July 1973
Copyright © 1973 by Lipid Research, Inc.
Synthesis of sulfate esters of phosphatidylglycerol (diphytanyl ether analog)
A. J. Hancock and M. Kates
Department of Biochemistry, University of Ottawa, Ottawa, Ontario, Canada, K1N 6N5
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 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.
Supplementary key words 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 • sulfation of phosphatidylglycerol • 3'-O-benzyl phosphatidyl-glycerol • NMR spectra • infrared spectra • optical rotations • thin-layer chromatography
Submitted on October 24, 1972
Accepted on February 27, 1973
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