Synthesis of propylene glycol phospholipids: analogues of α-lecithins and α-cephalins

Abstract

The synthesis of phospholipids derived from propylene glycol, structurally the least complex polyhydric alcohol to possess an asymmetric center, is described. Representatives of two types of propylene glycol phospholipids were prepared. They are analogues of α-(dipalmitoyl)lecithin and α-(dipalmitoyl)cephalin, and were obtained from D-propylene glycol via the following two series of intermediates: (A) α-trityl D-propylene glycol (I) → α-trityl, β-palmitoyl D-propylene glycol (II) → β-palmitoyl D-propylene glycol (III) → β-palmitoyl D-propylene glycol-α-(phenyl)phosphorylcholine chloride (IV) → β-palmitoyl D-propylene glycol-α-phosphorylcholine (V); and (B) I → II → III → β-palmitoyl D-propylene glycol-α-(phenyl)phosphoryl-N-carbobenzoxyethanolamine (VI) → β-palmitoyl D-propylene glycol-α-phosphorylethanolamine (VII). The palmitoyl D-propylene glycol-α-phosphorylcholine, a highly water-soluble compound, possesses strong hemolytic activity, whereas the palmitoyl D-propylene glycol-α-phosphorylethanolamine has no hemolytic properties whatsoever.