Portal de Periódicos da CAPES

A facile synthesis of 1-acyl ethylene glycol-2-phosphoryl-cholines

1973; Elsevier BV; Volume: 296; Issue: 3 Linguagem: Inglês

10.1016/0005-2760(73)90114-8

1879-145X

Kenichi K. Yabusaki, Michael A. Wells,

Synthetic Organic Chemistry Methods

A facile synthesis of ethylene glycol analogs of lecithins is described. The procedure involves direct acylation of ethylene glycol phosphorylcholine, prepared from sn-glycero-3-phosphorylcholine by periodate oxidation followed by reduction with NaBH4. The pure glycol lecithins are isolated in high yield after chromatography on silicic acid. The utility of the procedure is illustrated by the preparation of glycol lecithins with the following acyl chains: acetyl, butyryl, hexanoyl, octanoyl, and oleoyl. The availability of methods for the preparation of synthetic lecithins1, 2 make feasible studies of the physical, chemical and biological properties of lecithins to an extent heretofore impractical. In many instances a comparison of the properties of the ethylene glycol analogs, which contain only one fatty acyl chain, may provide additional information and insights into the properties of lecithins. However, the methods available for the synthesis of ethylene glycol analogs require total synthesis based on well established procedures for the total synthesis of lecithins3–5. While these methods are capable of yielding the desired products in a high degree of purity, they require several steps and are not readily adapted for the synthesis of analogs with short chain fatty acyl residues. We report here a generally applicable procedure involving the acylation of ethylene glycol phosphorylcholine, which is readily prepared from sn-glycero-3-phosphorylcholine.