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

Authors
  • Niu, Jun-Long1
  • Chai, Ke-Ke1
  • Zeng, Mei-Xing1
  • Wang, Tian-Tian1
  • Zhang, Chun-Yan1
  • Chen, Shuai1
  • Xu, Jing-Kun1, 2
  • Duan, Xue-Min1
  • 1 Jiangxi Science & Technology Normal University, Jiangxi Provincial Key Laboratory of Drug Design and Evaluation, School of Pharmacy, Nanchang, 330013, China , Nanchang (China)
  • 2 Qingdao University of Science and Technology, School of Chemistry and Molecular Engineering, Qingdao, 266042, China , Qingdao (China)
Type
Published Article
Journal
Chinese Journal of Polymer Science
Publisher
Chinese Chemical Society and Institute of Chemistry, CAS
Publication Date
Jan 14, 2019
Volume
37
Issue
5
Pages
451–461
Identifiers
DOI: 10.1007/s10118-019-2211-6
Source
Springer Nature
Keywords
License
Yellow

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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