Self-assembly properties of some chiral N-palmitoyl amino acid surfactants in aqueous solution

J Colloid Interface Sci. 2008 Mar 15;319(2):526-33. doi: 10.1016/j.jcis.2007.12.004. Epub 2007 Dec 7.

Abstract

Various chiral N-palmitoyl amino acid surfactants (AAS) derived from methionine, proline, leucine, threonine, phenylalanine and phenylglycine were prepared and converted to their sodium salt. The properties of the aggregates formed in aqueous solution were studied for both the optically-active compounds and their racemic mixture. Characterization was made by surface tensiometry, fluorimetry, dynamic light scattering, circular dichroism (CD) and transmission electron microscopy. It appeared that most of the AAS studied in this work spontaneously formed different types of aggregates, including micrometer-sized aggregates. No significant difference could be found between the critical aggregation concentration (cac) value of pure enantiomers and that of the racemic forms. CD spectra did not reveal any aggregation-induced chirality.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Circular Dichroism
  • Microscopy, Electron, Transmission
  • Nuclear Magnetic Resonance, Biomolecular
  • Palmitic Acid / chemistry*
  • Scattering, Radiation
  • Solutions / chemistry
  • Stereoisomerism
  • Surface-Active Agents / chemical synthesis*

Substances

  • Amino Acids
  • Solutions
  • Surface-Active Agents
  • Palmitic Acid