Phosphonic Acids, Phosphonates, and Phosphonolipids

The occurrence of organophosphonic acids and their derivatives has recently been reported in a wide variety of biological material. Their presence in lipids (phosphonolipids, as analogs of phospholipids) suggests participation in cell membrane structure. Alam and Bishop (1968) have reported the presence of derived aminoethyl-phosphonate in the phospholipid of human aortas. Choline phosphonate was detected in some of the aorta samples with atherosclerotic plaques and not detected in the other samples. No aminoethylphosphonate was found in the samples. 

Baer and Stanacev (1964) have reported the synthesis of dipalmitoyl L-a-glyceryl (2-aminoethyl) phosphonate, the first synthesis of a complex lipid containing phosphonic acid, and have shown spectra of L-a-(dipalmitoyl)cephalin and of dipalmitoyl L-a-phosphono(deoxy)cephalin. 

This report described the synthesis of diether phosphonolipids which resemble cephalins structurally. Infrared spectra were given for dihexadecanoyl L-a-glyceryl-(-2-aminoethyl) phosphonate and dihexadecanoyl L-a-glycerylphosphorylethanola-mine. 

The possibility of the natural existence of phosphonic acid analogs of lecithins prompted Baer and Stanacev (1965b) to synthesize such compounds, which they felt 

The occurrence of the phosphonic acid analogs of ethanolamine phosphate, serine phosphate, and choline phosphate, the three major constituents of phospholipids, has been established by Kittredge et al. (1967) in the sea anemone, Anthopleura xanthogrammica. They isolated and characterized 2-methylaminoethylphosphonic acid (XXXVII) and 2-trimethylaminoethylphosphonic acid (XXXVIII). 

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