Towards novel efficient monomeric surfactants based on serine, tyrosine and 4-hydroxyproline: synthesis and micellization properties

The synthesis of some novel monomeric serine- and tyrosine-based cationic and 4-hydroxyproline-based anionic surfactants, having a long lipophilic alkyl chain directly attached to the nitrogen atom of the amino acid, is described. The most efficient synthetic methodologies were established: reductive amination of the corresponding ‘fatty’ aldehydes, followed by methylation and deprotection (serine and tyrosine) to obtain the cationic surfactants; or reductive amination followed by saponification (4-hydroxyproline) to obtain the anionic ones. All the compounds were obtained in good to excellent yields. An assessment of their micellization properties and surface activity by tensiometry showed fairly good performance levels.