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Amperometric sensing of L-phenylalanine using a gold electrode modified with a metal organic framework, a molecularly imprinted polymer, and β-cyclodextrin-functionalized gold nanoparticles

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Abstract

The authors describe the construction of a molecularly imprinted electrochemical sensor for enantiomeric recognition of L-phenylalanine (L-Phe). Firstly, thiolated β-cyclodextrin (β-CD) and L-cysteine were used to functionalize gold nanoparticles via gold-thiol chemistry and to act as a basis for the formation of a microporous metal-organic framework (MOF). A MOF imprinted polymer was deposited on the functionalized gold nanoparticles by electropolymerization in the presence of the template L-Phe and the functional monomer 4-aminothiophenol. The modified electrode was characterized by cyclic voltammetry and electrochemical impedance spectroscopy in the presence of hexacyanoferrate acting as the redox probe. The electrode, operated best at 0.2 V vs. Ag/AgCl, exhibits excellent selectivity for L-Phe, with an enantioselectivity coefficient of 2.12 over D-Phe. In addition to its good enantiomeric selectivity, the sensor has a 0.33 pM detection limit which is much lower than that reported for other electrodes. The sensor has been successfully applied to the analysis of urine spiked with L-Phe.

Schematic of a microporous metal organic framework imprinting sensor for the analysis of enantiomers. Combined with MOF and β-CD, the sensor exhibits excellent selectivity and sensitivity for chiral assay of L-phenylalanine.

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Acknowledgements

The authors gratefully acknowledge the financial support from National Natural Science Foundation of China (No. 21375031), the Natural Science Foundation of Guangxi Province of China (No. 2015GXNSFAA139029, 2015GXNSFFA139005), Guangxi Colleges and Universities Key Laboratory of Food Safety and Detection, High Level Innovation Teams of Guangxi Colleges & Universities and Outstanding Scholars Program (Guijiaoren[2014] 49) for this research project.

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  1. Guangxi Key Laboratory of Electrochemical and Magnetochemical Function Materials, College of Chemistry and Bioengineering, Guilin University of Technology, Guilin, 541004, China

    Ting Wu, Xiaoping Wei, Xionghui Ma & Jianping Li

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  1. Ting Wu
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  2. Xiaoping Wei
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  3. Xionghui Ma
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Correspondence to Xiaoping Wei or Jianping Li.

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Wu, T., Wei, X., Ma, X. et al. Amperometric sensing of L-phenylalanine using a gold electrode modified with a metal organic framework, a molecularly imprinted polymer, and β-cyclodextrin-functionalized gold nanoparticles. Microchim Acta 184, 2901–2907 (2017). https://doi.org/10.1007/s00604-017-2281-5

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