An electrochemical chiral sensor for tryptophan enantiomers based on reduced graphene oxide/1,10-phenanthroline copper(II) functional composites

An electrochemical chiral sensor based on reduced graphene oxide (RGO) non-covalently functionalized with 1,10-phenanthroline copper(II) (PhenCu) complex has been developed for electrochemical discrimination of tryptophan (Trp) enantiomers. The formation and morphology of reduced graphene oxide/1,10-phenanthroline copper(II) (RGO/PhenCu) composites were confirmed by Fourier-transform infrared spectroscopy (FT-IR) and scanning electron microscopy (SEM). Cyclic voltammetry (CV) was employed to monitor the electrochemical behavior of RGO/PhenCu immobilized on glassy carbon electrode (RGO/PhenCu/GCE). The reduction in peak current was significantly different when the chiral sensor interacted with L-Trp and D-Trp. This suggested that RGO/PhenCu/GCE could be used as an electrochemical chiral sensor for the discrimination of Trp enantiomers. Further studies showed that the peak current decreased linearly along with an increasing percentage of L-Trp in the Trp mixture. The RGO/PhenCu/GCE electrochemical chiral sensor, with rapid recognition, good sensitivity and high stability, provided an efficient method to recognize and discriminate Trp enantiomers.

[1]  Baoxin Li,et al.  Visual chiral recognition of tryptophan enantiomers using unmodified gold nanoparticles as colorimetric probes. , 2014, Analytica chimica acta.

[2]  S. Yao,et al.  Self-assembled oligo(phenylene ethynylene)s/graphene nanocomposite with improved electrochemical performances for dopamine determination. , 2013, Analytica chimica acta.

[3]  M. Trojanowicz.  Enantioselective electrochemical sensors and biosensors: A mini-review , 2014 .

[4]  Yingzi Fu,et al.  The application of thionine-graphene nanocomposite in chiral sensing for Tryptophan enantiomers. , 2013, Bioelectrochemistry.

[5]  Yingzi Fu,et al.  Electrochemical enantioselective recognition of tryptophane enantiomers based on chiral ligand exchange. , 2012, Colloids and surfaces. B, Biointerfaces.

[6]  Chia-Liang Sun,et al.  The simultaneous electrochemical detection of ascorbic acid, dopamine, and uric acid using graphene/size-selected Pt nanocomposites. , 2011, Biosensors & bioelectronics.

[7]  A. Padarauskas,et al.  Enantioselective determination of protein amino acids in fertilizers by liquid chromatography-tandem mass spectrometry on chiral teicoplanin stationary phase. , 2014, Journal of agricultural and food chemistry.

[8]  Zhidong Chen,et al.  Separation of tryptophan enantiomers with polypyrrole electrode column by potential-induced technique , 2011 .

[9]  Jichang Wang,et al.  Self-assembly of osmium complexes on reduced graphene oxide: A case study toward electrochemical chiral sensing , 2012 .

[10]  A. I. Zad,et al.  In-situ electro-polymerization of graphene nanoribbon/polyaniline composite film: Application to sensitive electrochemical detection of dobutamine , 2014 .

[11]  J. Hernández-Ferrer,et al.  Multi-walled carbon nanotubes/graphene nanoribbons hybrid materials with superior electrochemical performance , 2014 .

[12]  Yingzi Fu,et al.  A reagentless enantioselective sensor for tryptophan enantiomers via nanohybrid matrices , 2013 .

[13]  Huan Wang,et al.  Chiral electrochemical sensing for tyrosine enantiomers on glassy carbon electrode modified with cysteic acid , 2013 .

[14]  M. Ersoz,et al.  An electrochemical biosensor based on human serum albumin/graphene oxide/3-aminopropyltriethoxysilane modified ITO electrode for the enantioselective discrimination of D- and L-tryptophan. , 2013, Biosensors & bioelectronics.

[15]  Xiaogang Qu,et al.  Electrochemical detection of dopamine using porphyrin-functionalized graphene. , 2012, Biosensors & bioelectronics.

[16]  C. Feng,et al.  Controllable synthesis of functional nanocomposites: Covalently functionalize graphene sheets with biocompatible L-lysine , 2012 .

[17]  Y. Sha,et al.  Temperature-sensitive electrochemical recognition of tryptophan enantiomers based on β-cyclodextrin self-assembled on poly(L-glutamic acid). , 2014, Analytical chemistry.

[18]  Jingquan Liu,et al.  Non-covalent interactions for synthesis of new graphene based composites , 2015 .

[19]  Kenneth A Johnson,et al.  The second enzyme in pyrrolnitrin biosynthetic pathway is related to the heme-dependent dioxygenase superfamily. , 2007, Biochemistry.

[20]  J. Goossens,et al.  NMR investigation of the complexation and chiral discrimination of pyrazole sulfonamide derivatives with cyclodextrins. , 2015, Carbohydrate polymers.

[21]  Zhimin Li,et al.  Non-covalently functionalizing a graphene framework by anthraquinone for high-rate electrochemical energy storage , 2015 .

[22]  C. Dong,et al.  Chiral discrimination between D- and L-tryptophan based on the alteration of the fluorescence lifetimes by the chiral additives. , 2010, Talanta.

[23]  Li Yang,et al.  Enantioselective open-tubular capillary electrochromatography using cyclodextrin-modified gold nanoparticles as stationary phase. , 2011, Journal of chromatography. A.

[24]  Nannan Liu,et al.  Regulation of DNA self-assembly and DNA hybridization by chiral molecules with corresponding biosensor applications. , 2015, Analytical chemistry.