The value of amino acids and vegetable oil derivatives as raw materials for the preparation of surfactants was recognized as soon as they were discovered early in the last century. Amino acid-based surfactants, which have an amino acid residue as a hydrophilic moiety, are reviewed with respect to their synthesis, properties and some applications. The review covers three main categories of amino acid-based surfactants: Nα-acyl, N-alkyl amide and O-alkyl ester derivatives among the linear or single chain amino acid-based surfactants; Nα, Nω-bis(Nα-acylarginine)α,ω-alkylendiamides, which are gemini amino acid-based surfactants; and 1-monoacyl-rac-glycero-3-O-(Nα-acetyl-L-amino acid) and 1,2-diacyl-rac-glycero-3-O-(Nα-acetyl-L-amino acid), both amino acid-based surfactants with glycerolipid-like structures.
1 April 2010 in Current Opinion in Chemical Biology
There is a pressing need for developing efficiently surfactants that are biodegradable and biocompatible. Surfactant molecules from renewable raw materials that mimic natural lipoamino acids are one of the preferred choices for food, pharmaceutical and cosmetic applications. Given their natural and simple structure they show low toxicity and quick biodegradation. The value of amino acids and vegetable oil derivatives as raw materials for the preparation of surfactants was recognized as soon as they were discovered early in the last century. The combination of polar amino acids/peptides (hydrophilic moiety) and non-polar long-chain compounds (hydrophobic moiety) for building up the amphiphilic structure has produced molecules with high surface activity. Our group has a wide experience in synthesis (chemical, enzymatic or, usually, by a combination of both methodologies) of amino acid-based surfactants obtained from the combination of natural saturated fatty acids, alcohols and amines with different amino acid head groups through ester and amide linkages. Thus, saturated single-chain, double-chain, and gemini surfactants of different ionic character have been found to be in all cases highly biodegradable, with low toxicity, ecotoxicity and irritation effects. Water solubility and self-aggregation properties were directly associated with the chemical structure of the molecule and only cationic lipoamino acids possessed antimicrobial activity. .