A diphytanyl ether analog of phosphatidylserine from a methanogenic bacterium, Methanobrevibacter arboriphilus.

Abstract

Several ninhydrin-positive lipids were found in methanogenic bacteria and the structure of one of them, designated as PNL2 from Methanobrevibacter arboriphilus, was identified as a diphytanyl ether analog of phosphatidylserine. The chromatographic behavior of the lipid on thin-layer plates and on a DEAE-cellulose column was identical to the ester form of phosphatidylserine. The infrared spectra showed the presence of amino, carboxyl, ether, and phosphate groups, and the absence of an ester linkage. The hydrophobic portion of the lipid was identified as diphytanyl glycerol diether on the basis of the mass spectrum of the acetolysis product and gas-liquid chromatography of the iodinated alkyl chain prepared by hydroiodic acid cleavage of PNL2. The fast atom bombardment-ionization and field desorption mass spectrum provided a molecular weight of 819 and several fragment ions consistent with the proposed structure. Hydrofluoric acid hydrolysis resulted in water-soluble products including serine, phosphoserine, and ammonia, which accounted for 95% of hydrolyzed PNL2. The lipid product of the hydrolysis was mainly the diether form of phosphatidic acid. This is the first report on the structural characterization of an amino-containing phospholipid in archaebacteria. Amino lipids have been found in many other methanogenic bacteria.