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

• Type: Article in International Scientific Journal
• Date: 2009

Authors

Goreti G Silva (Author) Other; Enrique E Rodriguez Borges (Author) FCUP; Eduardo F Marques (Author) FCUP; Luisa L C do Vale (Author) FCUP

Journal

Title: Tetrahedron

Vol. 65 No. 19

Pages: 4156-4164

ISSN: 0040-4020

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 25 Citations

Scopus - 27 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

CORDIS: Physical sciences > Chemistry > Organic chemistry ; Physical sciences > Chemistry > Physical chemistry

Associated Projects

115212_2009 - Uma nova abordagem à veiculação de fármacos: lipossomas cataniónicos e nanotubos baseados em derivados de aminoácidos

Other information

Authenticus ID: P-003-K1Q

DOI: 10.1016/j.tet.2009.03.043

Abstract (EN): 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 9