Enantiomeric recognition of amino acids by amphiphilic crown ethers in Langmuir monolayers

Langmuir : the ACS Journal of Surfaces and Colloids
Mounia BadisEwa Rogalska

Abstract

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.

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Citations

Jun 22, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Negar MoridiPatrick Shahgaldian
Mar 12, 2009·Chemical Communications : Chem Comm·Ritu Kataky, Paula Lopes
Jan 25, 2011·Physical Chemistry Chemical Physics : PCCP·D VollhardtS Dutta Banik
Jan 1, 2010·Sensors·Katsuhiko ArigaJonathan P Hill
Jul 1, 2006·Journal of Colloid and Interface Science·J Torrent-BurguésF Sanz
Mar 13, 2008·Science and Technology of Advanced Materials·Katsuhiko ArigaSomobrata Acharya
Aug 14, 2008·The Journal of Physical Chemistry. B·Yohann CorvisEwa Rogalska
Dec 6, 2008·The Journal of Physical Chemistry. a·Jacek KorchowiecEwa Rogalska
Nov 9, 2006·Journal of the American Chemical Society·Tsuyoshi MichinobuKatsuhiko Ariga
Apr 27, 2019·Journal of the American Chemical Society·Jennifer F NealHeather C Allen

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