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

Autor:	Eduardo F. Marques, S. Goreti Silva, J. Enrique Rodríguez-Borges, M. Luísa C. Vale
Rok vydání:	2009
Předmět:	chemistry.chemical_classification Organic Chemistry Cationic polymerization Biochemistry Reductive amination Aldehyde Chemical synthesis Serine chemistry Drug Discovery Organic chemistry Amination Saponification Alkyl
Zdroj:	Tetrahedron. 65:4156-4164
ISSN:	0040-4020
DOI:	10.1016/j.tet.2009.03.043
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::5b4721194fae301b956ef4dc6435ce8d https://doi.org/10.1016/j.tet.2009.03.043 Zobrazit plný text záznamu Full Text from ScienceDirect