Synthesis and enzymic hydrolysis of an o-alanyl ester of phosphatidyl glycerol

Abstract

A racemic 0-alanyl ester of phosphatidyl glycerol, containing one saturated and one unsaturated fatty acid, was synthesized by a reaction between silver benzyl- (γ-oleoyl-β-palmitoyl)-Dl-[alpha]-glycerol phosphate and DL-[alpha]-iodo-B-tert.-butyl-y-(N-tert.-butoxycarbonyl)-m-alanyl glycerol. The synthetic substance was hydrolysed by phospholipase A (EC 3.1.1.4), C (EC 3.1.4.3) and D. (EC 3.1.4.4). The results of the enzymic degradation and some other properties of this compound have been compared with those of amino acid derivatives of phosphatidyl glycerol from bacteria.