This paper describes the preparation and characterization of a self-assembled monolayer of per(6-deoxy6-thio)-beta-cyclodextrin (beta-CD-SH) on a gold electrode surface and the study of its inclusion interactions with D- and L-phenylalanine (Phe). The beta-CD-SH was self-synthesized and characterized by Fouriertransform infrared (FTIR) and nuclear magnetic resonance (NMR). The modified electrode surface was carefully characterized by cyclic voltammetry (CV) using potassium ferricyanide (Fe(CN)(6)](3-/4-)) and ferrocenecarboxylic acid (Fc-COOH) as redox probes. Phe was labeled with gold nanoparticles (n-Au-Phe), and the chiral recognition between them and beta-CD-SH on the surface of an electrode was carried out. The methods of gold labeling and silver staining was strengthened by SEM. Finally, silver enhancement was monitored by differential pulse voltammetry (DPV). The DPV signal was greatly amplified by the silver atoms coated on the n-Au. The proposed method distinguished D- from L-Phe with an enantioselectivity coefficient of 3.64. The association constants of o-, m- and p-ABA with beta-CD-SH at pH 4.0 were calculated to be 2.84 x 10(4), 1.94 x 10(4), and 3.43 x 10(5) mol(-1) L, respectively. (C) 2015 Elsevier B.V. All rights reserved.