Molecular Recognition of Phenylalanine Enantiomers onto a Solid Surface Modified with Electropolymerized Pyrrole-beta-Cyclodextrin Conjugate

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Date
2019
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WILEY-V C H VERLAG GMBH, POSTFACH 101161, 69451 WEINHEIM, GERMANY
Abstract
We report the electrochemical deposition of a beta-cyclodextrin pyrrole conjugate (Py-beta-CD) on an electrode surface including i) characterization based on surface-enhanced Raman scattering and field-emission scanning electron microscopy; ii) studies of the molecular recognition of enantiomers of phenylalanine methyl ester hydrochlorides (Phe) based on linear sweep voltammetry and a quartz crystal microbalance. The PPy-beta-CD polymeric layer on a metallic substrate is distinguished by its inhomogeneity, in which both highly ordered beta-CD units and highly disordered polymer chains are observed. The voltammetric recognition results showed that PPy-beta-CD exhibited a higher sensitivity for d-Phe (138 +/- 15)x10(3) than for l-Phe (6 +/- 1)x10(3) within the concentration range 0.1-0.75 mM (n=3) despite the differences in the polymer arrangement on the surface. A possible mechanism of molecular recognition of phenylalanine enantiomers is discussed.
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beta-cyclodextrin pyrrole conjugate, electrochemical polymerization, enantiomer recognition, voltammetry, quartz crystal microbalance
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