Enantiomeric recognition of amino acids by amphiphilic crown ethers in Langmuir monolayers.
Four new chiral, amphiphilic crown ethers differing by the hydrophobic tailgroups were synthesized, and their capacity to recognize enantiomeric amino acids was examined using Langmuir films. Surface pressure and surface potential measurements performed on the subphases containing L or D enantiomers of alanine, valine, phenylglycine, and tryptophane indicate that the crown ethers forming the monolayer interact with the amino acids. The effects observed are ascribed to the formation of host-guest complexes. The differences in the magnitude of the effects measured show that the crown ethers are capable of discriminating between different amino acids as well as the enantiomers. Our results demonstrate that the structure of the monolayer plays a decisive role in the molecular recognition process including chiral recognition.
Badis
Mounia
M
Equipe de Physico-chimie des Colloïdes, UMR 7565 CNRS/Université Henri Poincaré Nancy 1, Faculté des Sciences, BP 239, 54506 Vandoeuvre-lès-Nancy Cedex, France.
Tomaszkiewicz
Iwona
I
Joly
Jean-Pierre
JP
Rogalska
Ewa
E
D000596:Amino Acids / Q000737:chemistry*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D043844:Crown Ethers / Q000138:chemical synthesis / Q000737:chemistry*; D008567:Membranes, Artificial; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013499:Surface Properties
D000596:Amino Acids; D043844:Crown Ethers; D008567:Membranes, Artificial