Straightforward Method for the Preparation of Lysine-Based Double-Chained Anionic Surfactants

Abstract

Double-chained surfactants with potential biocompatibility have been prepared in high yields by lysine acylation with four natural saturated fatty acids (C₆ to C₁₂) and with cis-undec-5-enoic acid. The surfactants were found to assemble into nanotubules in aqueous medium and, when mixed with a commercial cationic surfactant, to spontaneously form liposomes.

Keywords:

• Carbodiimide
• Coupling
• Fatty acid
• Liposome
• Lysine
• Peptide
• Surfactant

ACKNOWLEDGMENTS

The authors thank Fundação para a Ciência e Tecnologia (FCT, Lisbon-Portugal) for financial support through project POCTI/QUI/44296/2002 and through pluriannual funding to research unit Centro de Investigação em Química da Universidade do Porto (CIQUP, Porto-Portugal). Thanks are due to Cláudia Correia for laboratory assistance.