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

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

doi:10.1007/s10118-019-2211-6

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

ARTICLE | Updated：2021-02-18

- Boc-phenylalanine Grafted Poly(3,4-propylenedioxythiophene) Film for Electrochemically Chiral Recognition of 3,4-Dihydroxyphenylalanine Enantiomers
- Boc-phenylalanine Grafted Poly(3,4-propylenedioxythiophene) Film for Electrochemically Chiral Recognition of 3,4-Dihydroxyphenylalanine Enantiomers
- Chinese Journal of Polymer Science 2019年37卷第5期页码：451-461
- Affiliations：
  
  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
- Author bio：
  
  chenshuai@ms.xjb.ac.cn (S.C.)
  xujingkun@jxstnu.edu.cn (J.K.X.)
  duanxuemin@126.com (X.M.D.)
- Funds：
  
  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.
- DOI：10.1007/s10118-019-2211-6
  中图分类号：
- 收稿：2018-10-15，
  
  修回：2018-11-26，
  
  录用：2018-12-11，
  
  网络首发：2019-01-14，
  
  纸质出版：2019-05
- Accepted：
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Citation: Niu, J. L.; Chai, K. K.; Zeng, M. X.; Wang, T. T.; Zhang, C. Y.; Chen, S.; Xu, J. K.; Duan, X. M. Boc-phenylalanine grafted poly(3,4-propylenedioxythiophene) film for electrochemically chiral recognition of 3,4-dihydroxyphenylalanine enantiomers. Chinese J. Polym. Sci. 2019, 37, 451–461

Jun-Long Niu, Ke-Ke Chai, Mei-Xing Zeng, et al. 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.
Citation: Niu, J. L.; Chai, K. K.; Zeng, M. X.; Wang, T. T.; Zhang, C. Y.; Chen, S.; Xu, J. K.; Duan, X. M. Boc-phenylalanine grafted poly(3,4-propylenedioxythiophene) film for electrochemically chiral recognition of 3,4-dihydroxyphenylalanine enantiomers. Chinese J. Polym. Sci. 2019, 37, 451–461 DOI： 10.1007/s10118-019-2211-6.

Jun-Long Niu, Ke-Ke Chai, Mei-Xing Zeng, et al. 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.

摘要

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-2

-thieno[3

][1

dioxepin-3-yl)methyl 2-[(

tert

-butoxycarbonyl)amino]-3-phenylpropanoate (ProDOT-Boc-Phe)

were synthesized. Chiral poly[(3

4-dihydro-2

-thieno[3

][1

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.

关键词

Keywords

references

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