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Electrochemical recognition for tryptophan enantiomers based on 3, 4, 9, 10-perylenetetracarboxylic acid–chitosan composite film

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Abstract

A novel and simple chiral sensing platform had been successfully fabricated by means of amidation reaction between 3, 4, 9, 10-perylenetetracarboxylic acid (PTCA) and chitosan (CS) to form 3, 4, 9, 10-perylenetetracarboxylic acid–chitosan (PTCA–CS) composite film. Since CS has chiral center and PTCA has excellent electrical conductivity, the PTCA–CS composite modified glassy carbon electrode (PTCA–CS/GCE) could be treated as an effective electrochemical chiral sensor and applied for chiral discrimination of tryptophan (Trp) enantiomers theoretically. PTCA–CS composite was characterized by Fourier transform infrared (FTIR) spectroscopy and cyclic voltammetry (CV). When the prepared chiral sensing interface interacted with tryptophan isomers, a higher selectivity was received from D-Trp by differential pulse voltammetry (DPV). It indicated that the PTCA–CS/GCE can be treated as an electrochemical chiral sensor for the discrimination of Trp enantiomers. Further study demonstrated that the peak currents were linearly increased with the increasing percentage of L-Trp of Trp racemic mixture. Furthermore, the enantioselective interaction of the PTCA–CS/GCE was systematically studied by other experimental factors, such as the incubation time and acidity.

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Funding

This work was supported by the National Natural Science Foundation of China (51262027), the financial support of the Natural Science Foundation of Gansu Province (1104GKCA019 and 1010RJZA023), the Science and Technology Tackle Key Problem Item of Gansu Province (2GS064-A52-036-08) and the fund of the State Key Laboratory of Solidification Processing in NWPU (SKLSP201011).

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Authors and Affiliations

  1. Key Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education of China, Key Laboratory of Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, 730070, People’s Republic of China

    Zunli Mo, Xiaohui Niu, Huhu Gao, Zhenliang Li, Shujuan Meng & Ruibin Guo

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  1. Zunli Mo
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  2. Xiaohui Niu
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  3. Huhu Gao
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Correspondence to Zunli Mo.

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Mo, Z., Niu, X., Gao, H. et al. Electrochemical recognition for tryptophan enantiomers based on 3, 4, 9, 10-perylenetetracarboxylic acid–chitosan composite film. J Solid State Electrochem 22, 2405–2412 (2018). https://doi.org/10.1007/s10008-018-3960-9

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  • DOI: https://doi.org/10.1007/s10008-018-3960-9

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