SYNTHESIS OF NATURALLY OCCURRING PHYTANYL DIETHER ANALOGS OF PHOSPHATIDYL GLYCEROPHOSPHATE AND PHOSPHATIDYL GLYCEROL

The diastereomers of the diphytanyl glycerol ether analogs of phosphatidyl glycerophosphate and phosphatidyl glycerol have been synthesized chemically and compared with the respective natural isomer isolated from the extremely halophilic bacterium, Halobacterium cutirubrum. The structure and configuration of the natural isomer of the phosphatidyl glycerophosphate was thus shown to be 2,3-di-O-(3′R,7′R, 11′R,15-tetramethylhexadecyl)-sn-glycero-1-phosphoryl-3″-sn- glycero-1″-phosphate (XVb); the natural phosphatidyl glycerol was shown to have the structure and configuration, 2,3-di-O-(3′R,7′R,11′R,15-tetramethylhexadecyl)-sn-gly cero-1-phosphoryl-3″-sn-glycerol(XVIIIb). The implications of these findings on the biosynthetic mechanisms for these unusual phosphatides are discussed. © 1969.