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Boc-phenylalanine Grafted Poly(3,4-propylenedioxythiophene) Film for Electrochemically Chiral Recognition of 3,4-Dihydroxyphenylalanine Enantiomers

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Abstract

To prepare chiral monomer with single chiral center and higher stereospecificity, a pair of amino-functionalized chiral 3,4-propylenedioxythiophene (ProDOT) derivatives, chiral (3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepin-3-yl)methyl 2-[(tert-butoxycarbonyl) amino]-3-phenylpropanoate (ProDOT-Boc-Phe), were synthesized. Chiral poly[(3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepin-3-yl)methyl 2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoate] (PProDOT-Boc-Phe) modified electrodes were synthesized via potentiostatic polymerization of chiral ProDOT-Boc-Phe. Chiral PProDOT-Boc-Phe films displayed good reversible redox activities. The enantioselective recognition between chiral PProDOT-Boc-Phe modified glassy carbon electrodes and DOPA enantiomers was achieved by different electrochemical technologies, including cyclic voltammetry (CV), square wave voltammetry (SWV), and differential pulse voltammetry (DPV). (D)-PProDOT-Boc-Phe and (L)-PProDOT-Boc-Phe showed higher peak current responses toward L-DOPA and D-DOPA, respectively.

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Acknowledgments

The authors are grateful to the National Natural Science Foundation of China (Nos. 51762020 and 51603095), the Natural Science Foundation of Jiangxi Province (Nos. 20171ACB20026 and 20181BAB206015), the Jiangxi Provincial Department of Education (No. GJJ170662), the Innovation Driven "5511" the Natural Science Foundation of Jiangxi Province (No. 20165BCB18016), Students Innovation and Entrepreneurship Training Program (No. 20181204066), Projects for Postgraduate Innovation in Jiangxi (No. YC2017-X19), and the Jiangxi Provincial Key Laboratory of Drug Design and Evaluation (No. 20171BCD40015) for their financial support of this work.

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Authors and Affiliations

  1. Jiangxi Provincial Key Laboratory of Drug Design and Evaluation, School of Pharmacy, Jiangxi Science & Technology Normal University, Nanchang, 330013, China

    Jun-Long Niu, Ke-Ke Chai, Mei-Xing Zeng, Tian-Tian Wang, Chun-Yan Zhang, Shuai Chen, Jing-Kun Xu & Xue-Min Duan

  2. School of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, 266042, China

    Jing-Kun Xu

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  1. Jun-Long Niu
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Correspondence to Shuai Chen, Jing-Kun Xu or Xue-Min Duan.

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Niu, JL., Chai, KK., Zeng, MX. et al. Boc-phenylalanine Grafted Poly(3,4-propylenedioxythiophene) Film for Electrochemically Chiral Recognition of 3,4-Dihydroxyphenylalanine Enantiomers. Chin J Polym Sci 37, 451–461 (2019). https://doi.org/10.1007/s10118-019-2211-6

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