Jump to main content
Jump to site search

Issue 11, 2011
Previous Article Next Article

Langmuir monolayers of a cholesterol-armed cyclen complex that can control enantioselectivity of amino acid recognition by surface pressure

Author affiliations

Abstract

The cholesterol-armed cyclen Na+ complex formed stable Langmuir monolayers at the air–water interface. The πA isotherm displayed a reasonable limiting molecular area of ∼1.57 nm2 and the areas expanded when amino acids were dissolved in water, indicating the efficient accommodation in the monolayers. Brewster angle microscopy (BAM) images exhibited almost no defects of the compressed Langmuir monolayers regardless of the presence of amino acids. Based on the idea that the increase in the limiting molecular areas corresponds to the amount of the adsorbed amino acid, the binding constants of three enantiomeric amino acids, namely valine (Val), leucine (Leu), and phenylalanine (Phe), were calculated at different surface pressures. Remarkably, a surface pressure dependent enantioselectivity of amino acid recognition was observed. Upon compression of the monolayers, the binding constants of amino acids increased accompanying an inversion of chiral selectivity from the D- to L-form in the case of Val and, conversely, from L- to D-form in the case of Phe.

Graphical abstract: Langmuir monolayers of a cholesterol-armed cyclen complex that can control enantioselectivity of amino acid recognition by surface pressure

Back to tab navigation

Publication details

The article was received on 01 Oct 2010, accepted on 07 Dec 2010 and first published on 07 Jan 2011


Article type: Paper
DOI: 10.1039/C0CP01990A
Citation: Phys. Chem. Chem. Phys., 2011,13, 4895-4900
  •   Request permissions

    Langmuir monolayers of a cholesterol-armed cyclen complex that can control enantioselectivity of amino acid recognition by surface pressure

    T. Michinobu, S. Shinoda, T. Nakanishi, J. P. Hill, K. Fujii, T. N. Player, H. Tsukube and K. Ariga, Phys. Chem. Chem. Phys., 2011, 13, 4895
    DOI: 10.1039/C0CP01990A

Search articles by author

Spotlight

Advertisements