Synthesis and biological properties of dicationic arginine–diglycerides

Abstract

A novel family of dicationic arginine–diglyceride surfactants, 1,2-diacyl-3-O-(L-arginyl)-rac-glycerol·2HCl (XXR) with alkyl chain lengths in the range of C₈–C₁₄ was prepared. These new surfactants can be regarded as analogues of lecithins. They have two hydrophobic tails of identical fatty acid chains attached to the glycerol through ester bonds and a dicationic polar head from arginine instead of the zwitterionic on the lecithins. These new compounds can be classified as multifunctional surfactants with self-aggregation behaviour comparable to that of short-chain lecithins. They have antimicrobial activity similar to that of the conventional cationic surfactants and are as harmless as amphoteric betaines.