Citation: Jun-Long Niu, Ke-Ke Chai, Mei-Xing Zeng, Tian-Tian Wang, Chun-Yan Zhang, Shuai Chen, Jing-Kun Xu, Xue-Min Duan. Boc-phenylalanine Grafted Poly(3,4-propylenedioxythiophene) Film for Electrochemically Chiral Recognition of 3,4-Dihydroxyphenylalanine Enantiomers[J]. Chinese Journal of Polymer Science, ;2019, 37(5): 451-461. doi: 10.1007/s10118-019-2211-6 shu

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

a.
Jiangxi Provincial Key Laboratory of Drug Design and Evaluation, School of Pharmacy, Jiangxi Science & Technology Normal University, Nanchang 330013, China
b.
School of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China

Corresponding author: Shuai Chen, chenshuai@ms.xjb.ac.cn Jing-Kun Xu, xujingkun@jxstnu.edu.cn Xue-Min Duan, duanxuemin@126.com
Received Date: 15 October 2018
Revised Date: 26 November 2018
Accepted Date: 10 December 2018
Available Online: 14 January 2019

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.
- Chiral conducting polymer,
- Amino acids,
- Chiral sensors,
- 3,4-Dihydroxyphenylalanine,
- Electrochemistry
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