Synthesis and Characterization of <italic style="font-style: italic">D</italic>-/<italic style="font-style: italic">L</italic>-methionine Grafted PEDOTs for Selective Recognition of 3,4-Dihydroxyphenylalanine Enantiomers

Li-qi Dong; Du-fen Hu; Xue-min Duan; Zhi-peng Wang; Kai-xin Zhang; Xiao-fei Zhu; Hui Sun; You-shan Zhang; Jing-kun Xu

doi:10.1007/s10118-016-1772-x

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Synthesis and Characterization of D-/L-methionine Grafted PEDOTs for Selective Recognition of 3,4-Dihydroxyphenylalanine Enantiomers

PAPERS | Updated：2021-05-12

- Synthesis and Characterization of D-/L-methionine Grafted PEDOTs for Selective Recognition of 3,4-Dihydroxyphenylalanine Enantiomers
- Synthesis and Characterization of D-/L-methionine Grafted PEDOTs for Selective Recognition of 3,4-Dihydroxyphenylalanine Enantiomers
- Chinese Journal of Polymer Science 2016年34卷第5期页码：563-577
- Affiliations：
  
  School of Pharmacy, Jiangxi Science & Technology Normal University, Nanchang 330013, China
- Author bio：
  
  Xue-min Duan (段学民), E-mail: duanxuemin@126.com
  Jing-kun Xu (徐景坤), E-mail: xujingkun@tsinghua.org.cn
- Funds：
  
  This work was financially supported by the National Natural Science Foundation of China(51263010);This work was financially supported by the National Natural Science Foundation of China(51303073);This work was financially supported by the National Natural Science Foundation of China(51272096);Natural Science Foundation of Jiangxi Province(20142BAB206028);the Science and Technology Landing Plan of Universities in Jiangxi Province(KJLD14069);Provincial Project for Postgraduate Innoviation in Jiangxi Science and Technology Normal University(YC2014-X27)
- DOI：10.1007/s10118-016-1772-x
  中图分类号：
- 收稿：2015-10-31，
  
  修回：2015-12-5，
  
  录用：2015-12-5，
  
  纸质出版：2016-05
- Accepted：
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Li-qi Dong, Du-fen Hu, Xue-min Duan, 等. Synthesis and Characterization of D-/L-methionine Grafted PEDOTs for Selective Recognition of 3,4-Dihydroxyphenylalanine Enantiomers[J]. Chinese Journal of Polymer Science, 2016,34(5):563-577. DOI: 10.1007/s10118-016-1772-x.

Li-qi Dong, Du-fen Hu, Xue-min Duan, et al. Synthesis and Characterization of D-/L-methionine Grafted PEDOTs for Selective Recognition of 3,4-Dihydroxyphenylalanine Enantiomers[J]. Chinese Journal of Polymer Science, 2016, 34(5): 563-577. DOI: 10.1007/s10118-016-1772-x.
Li-qi Dong, Du-fen Hu, Xue-min Duan, 等. Synthesis and Characterization of D-/L-methionine Grafted PEDOTs for Selective Recognition of 3,4-Dihydroxyphenylalanine Enantiomers[J]. Chinese Journal of Polymer Science, 2016,34(5):563-577. DOI: 10.1007/s10118-016-1772-x. DOI：

Li-qi Dong, Du-fen Hu, Xue-min Duan, et al. Synthesis and Characterization of D-/L-methionine Grafted PEDOTs for Selective Recognition of 3,4-Dihydroxyphenylalanine Enantiomers[J]. Chinese Journal of Polymer Science, 2016, 34(5): 563-577. DOI: 10.1007/s10118-016-1772-x. DOI：

摘要

Abstract

Two pairs of amino-acid functionalized poly(3

4-ethylenedioxythiophene) (PEDOT) derivatives

namely

poly(

tert

-butoxycarbonyl)-

-methionyl (3

4-ethylenedioxythiophene-2'-yl)methylamide) (

-PEDOT-Boc-Met) and poly(

tert

-butoxycarbonyl)-

-methionyl (3

4-ethylenedioxythiophene-2'-yl)methylamide) (

-PEDOT-Boc-Met); poly(

-methionyl (3

4-ethylenedioxythiophene-2'-yl)methylamide) (

-PEDOT-Met) and poly(

-methionyl (3

4-ethylenedioxythiophene-2'-yl)methylamide) (

-PEDOT-Met) were synthesized

via

chemical oxidative polymerization of corresponding monomers. The structural characterization

spectroscopic properties and thermal stability of these monomers and polymers were systematically explored by FTIR spectra

Raman spectra

XRD spectra

UV-Vis spectra and thermogravimetric analysis. As chiral electrode materials

these polymers were employed to successfully recognize 3

4-dihydroxyphenylalanine (DOPA) enantiomers by cyclic voltammetry (CV) in sulphuric acid solution. The measurement results reveal that the tendency was hetero-chiral interaction between

-PEDOT-Met/PVA/GCE and

-DOPA

-PEDOT-Met/PVA/GCE and

-DOPA

respectively. Also

the mechanism of chiral discrimination was discussed. All the results implied that the combination of electrochemical molecular recognition technology and chiral PEDOT materials can be a promising approach for chiral recognition and may open new opportunities for facile

biocompatible

sensitive and robust chiral assays in biochemical applications.

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Keywords

references

Gal, J., “Chirality in drug research”, Wiley-VCH, Weinheim, 2006, p.3

B. Testa , W. Trager . Chirality , 1990 . 2 129 DOI: 10.1002/(ISSN)1520-636X http://doi.org/10.1002/(ISSN)1520-636X .

T. Ikai , Y. Okamoto . Chem. Rev. , 2009 . 109 6077 DOI: 10.1021/cr8005558 http://doi.org/10.1021/cr8005558 .

M. Islam , J. Mahdi , I. Bowen . Drug Safety , 1997 . 17 149 DOI: 10.2165/00002018-199717030-00002 http://doi.org/10.2165/00002018-199717030-00002 .

Y. Okamoto , E. Yashima . Angew. Chem. Int. Ed. , 1998 . 37 1020 DOI: 10.1002/(ISSN)1521-3773 http://doi.org/10.1002/(ISSN)1521-3773 .

K. J. Rentsch . Biochem. Bioph. Meth. , 2002 . 54 1 DOI: 10.1016/S0165-022X(02)00124-0 http://doi.org/10.1016/S0165-022X(02)00124-0 .

W. Walther , T. Netscher . Chirality , 1996 . 8 397 DOI: 10.1002/(ISSN)1520-636X http://doi.org/10.1002/(ISSN)1520-636X .

W. Poewe , A. Antonini , J. Zijlmans , P. Burkhard , F. Vingerhoets . Clin. Interv. Aging. , 2010 . 5 229 .

G. Pezzoli , M. Zini . Expert. Opin. Pharmaco. , 2010 . 11 627 DOI: 10.1517/14656561003598919 http://doi.org/10.1517/14656561003598919 .

T. Alexander , C. Sortwell , C. Sladek , R. Roth , K. Steece-Collier . Cell Transplant. , 1997 . 6 309 DOI: 10.1016/S0963-6897(97)00031-6 http://doi.org/10.1016/S0963-6897(97)00031-6 .

W. Chen , R. Duan , Q. Fan , Z. Bai , S. Huang . Chinese J. Polym. Sci. , 2014 . 32 ( 4 ): 458 DOI: 10.1007/s10118-014-1409-x http://doi.org/10.1007/s10118-014-1409-x .

W. Chen , Q. Bin , Z. Bai , X. Zhou , X. Xie . Chinese J. Polym. Sci. , 2013 . 31 ( 12 ): 1725 DOI: 10.1007/s10118-013-1312-x http://doi.org/10.1007/s10118-013-1312-x .

K. Bodenhöfer , A. Hierlemann , J. Seemann , G. Gauglitz , B. Koppenhoefer , W. Gpel . Nature , 1997 . 387 577 DOI: 10.1038/42426 http://doi.org/10.1038/42426 .

V. Schurig , W. Buerkle . J. Am. Chem. Soc. , 1982 . 104 7573 DOI: 10.1021/ja00390a031 http://doi.org/10.1021/ja00390a031 .

V. Schurig . J. Chromatogr. A , 2001 . 906 275 DOI: 10.1016/S0021-9673(00)00505-7 http://doi.org/10.1016/S0021-9673(00)00505-7 .

R. Kuhn , F. Erni , T. Bereuter , J. Haeusler . Anal. Chem. , 1992 . 64 2815 DOI: 10.1021/ac00046a026 http://doi.org/10.1021/ac00046a026 .

F. Lelievre , P. Gareil . Anal. Chem. , 1997 . 69 385 DOI: 10.1021/ac960606z http://doi.org/10.1021/ac960606z .

L. Sanchez-Hernandez , M. Guijarro-Diez , M. Marina , A. Crego . Electrophoresis , 2014 . 35 12 DOI: 10.1002/elps.v35.1 http://doi.org/10.1002/elps.v35.1 .

Y. Fu , L. Wang , Q. Chen , J. Zhou . Sensor Actuat. B: Chem. , 2011 . 155 140 DOI: 10.1016/j.snb.2010.11.038 http://doi.org/10.1016/j.snb.2010.11.038 .

L. Chen , F. Chang , L. Meng , M. Li , Z. Zhu . Analyst , 2014 . 139 2243 DOI: 10.1039/c4an00098f http://doi.org/10.1039/c4an00098f .

J. Gooding . Electrochim. Acta , 2005 . 50 3049 DOI: 10.1016/j.electacta.2004.08.052 http://doi.org/10.1016/j.electacta.2004.08.052 .

Y. Huang , Q. Han , Q. Zhang , L. Guo , D. Guo , Y. Fu . Electrochim. Acta , 2013 . 113 564 DOI: 10.1016/j.electacta.2013.09.123 http://doi.org/10.1016/j.electacta.2013.09.123 .

G. Mirri , S. Bull , P. Horton , T. James , L. Male , J. Tucker . J. Am. Chem. Soc. , 2010 . 132 8903 DOI: 10.1021/ja103462x http://doi.org/10.1021/ja103462x .

T. Nakanishi , M. Matsunaga , M. Nagasaka , T. Asahi , T. Osaka . J. Am. Chem. Soc. , 2006 . 128 13322 DOI: 10.1021/ja062380f http://doi.org/10.1021/ja062380f .

L. Wu , L. Zhang , L. Lu , X. Duan , J. Xu , T. Nie . Chinese J. Polym. Sci. , 2014 . 32 ( 8 ): 1019 DOI: 10.1007/s10118-014-1484-z http://doi.org/10.1007/s10118-014-1484-z .

Y. Yao , Y. Wen , L. Zhang , Z. Wang , H. Zhang , J. Xu . Anal. Chim. Acta. , 2014 . 831 38 DOI: 10.1016/j.aca.2014.04.059 http://doi.org/10.1016/j.aca.2014.04.059 .

L. Zhang , Y. Wen , Y. Yao , J. Xu , X. Duan , G. Zhang . Electrochim. Acta , 2014 . 116 343 DOI: 10.1016/j.electacta.2013.11.042 http://doi.org/10.1016/j.electacta.2013.11.042 .

S. Matsushita , B. Yan , S. Yamamoto , Y. Jeong , K. Akagi . Angew. Chem. Int. Ed. , 2014 . 53 1659 DOI: 10.1002/anie.201308462 http://doi.org/10.1002/anie.201308462 .

Y. Jeong , H. Goto , S. Iimura , T. Asano , K. Akagi . Curr. Appl. Phys. , 2006 . 6 960 DOI: 10.1016/j.cap.2005.01.047 http://doi.org/10.1016/j.cap.2005.01.047 .

S. Shita , Y. Jeong , K. Akagi . Chem. Commun. , 2013 . 49 1883 DOI: 10.1039/c2cc37116b http://doi.org/10.1039/c2cc37116b .

H. Goto , Y. Yeong , K. Akagi . Macromol. Rapid Commun. , 2005 . 26 164 DOI: 10.1002/(ISSN)1521-3927 http://doi.org/10.1002/(ISSN)1521-3927 .

D. Hu , B. Lu , X. Duan , J. Xu , L. Zhang , K. Zhang , S. Zhang , S. Zhen . RSC Adv. , 2014 . 4 35597 DOI: 10.1039/C4RA05075D http://doi.org/10.1039/C4RA05075D .

B. Lu , Y. Lu , Y. Wen , X. Duan , J. Xu , S. Chen , L. Zhang . Int. J. Electrochem. Sci. , 2013 . 8 2826 .

L. Dong , B. Lu , X. Duan , J. Xu , D. Hu , K. Zhang , X. Zhu , H. Sun , S. Ming , Z. Wang , S. Zhe , Polym. Sci. J. . Part A: Polym. Chem. , 2015 . 53 2238 DOI: 10.1002/pola.v53.19 http://doi.org/10.1002/pola.v53.19 .

Y. Jeong , K. Akagi . J. Mater. Chem. , 2011 . 21 10472 DOI: 10.1039/c0jm04183a http://doi.org/10.1039/c0jm04183a .

Y. Nishizuka . Nature , 1988 . 334 661 DOI: 10.1038/334661a0 http://doi.org/10.1038/334661a0 .

M. Gómez-Mingot , J. Iniesta , V. Montiel , R. Kadara , C. Banks . Sensor Actuat. B Chem. , 2011 . 155 831 DOI: 10.1016/j.snb.2011.01.056 http://doi.org/10.1016/j.snb.2011.01.056 .

Y. Lu , Y. Wen , B. Lu , X. Duan , J. Xu , L. Zhang , Y. Huang . Chinese J. Polym. Sci. , 2012 . 30 ( 6 ): 824 DOI: 10.1007/s10118-012-1195-2 http://doi.org/10.1007/s10118-012-1195-2 .

H. Sun , B. Lu , D. Hu , X. Duan , J. Xu , S. Zhen , K. Zhang , X. Zhu , L. Dong , D. Mo . Chinese J. Polym. Sci. , 2015 . 33 ( 11 ): 1527 DOI: 10.1007/s10118-015-1693-0 http://doi.org/10.1007/s10118-015-1693-0 .

L. Zhang , Y. Wen , Y. Yao , Z. Wang , X. Duan , J. Xu . Chinese Chem. Lett. , 2014 . 25 517 DOI: 10.1016/j.cclet.2013.12.020 http://doi.org/10.1016/j.cclet.2013.12.020 .

M. Baker , S. Walsh , Z. Schwartz , B. Boyan . J. Biomed. Mater. Res. Part B: Appl. Biomater. , 2012 . 100 1451 .

B. Lu , S. Zhen , S. Zhang , J. Xu , G. Zhao . Polym, Chem. , 2014 . 5 4896 DOI: 10.1039/C4PY00529E http://doi.org/10.1039/C4PY00529E .

S. Ming , S. Zhen , K. Lin , L. Zhao , J. Xu , B. Lu . ACS Appl. Mater. Inter. , 2015 . 7 11089 DOI: 10.1021/acsami.5b01188 http://doi.org/10.1021/acsami.5b01188 .

S. Garreau , G. Louarn , J. Buisson , G. Froyer , S. Lefrant . Macromolecules , 1999 . 32 6807 DOI: 10.1021/ma9905674 http://doi.org/10.1021/ma9905674 .

W. Chiu , J. Travaš-Sejdić , R. Cooney , G. Bowmaker . Synth. Met. , 2005 . 155 80 DOI: 10.1016/j.synthmet.2005.06.012 http://doi.org/10.1016/j.synthmet.2005.06.012 .

J. Xiong , F. Jiang , H. Shi , J. Xu , C. Liu , W. Zhou , Q. Jiang , Z. Zhu , Y. Hu . ACS Appl. Mater. Interfaces , 2015 . 7 14917 DOI: 10.1021/acsami.5b03692 http://doi.org/10.1021/acsami.5b03692 .

K. Aasmundtveit , E. Samuelsen , O. Inganas , L. Petterson , T. Johansson , S. Ferrer . Synth. Met. , 2000 . 113 93 DOI: 10.1016/S0379-6779(00)00181-8 http://doi.org/10.1016/S0379-6779(00)00181-8 .

K. Lin , S. Ming , S. Zhen , Y. Zhao , B. Lu , J. Xu . Polym. Chem. , 2015 . 6 4575 DOI: 10.1039/C5PY00410A http://doi.org/10.1039/C5PY00410A .

Y. Kang , J. Oh , Y. Kim , J. Kim , H. Kim . Chem. Commun. , 2010 . 46 5665 DOI: 10.1039/c0cc01071e http://doi.org/10.1039/c0cc01071e .

Q. Han , Q. Chen , Y. Wang , J. Zhou , Y. Fu . Electroanalysis , 2012 . 24 332 DOI: 10.1002/elan.v24.2 http://doi.org/10.1002/elan.v24.2 .

M. Eslami , M. Namazian , H. Zare . Electrochim. Acta , 2013 . 88 543 DOI: 10.1016/j.electacta.2012.10.086 http://doi.org/10.1016/j.electacta.2012.10.086 .

A. Brun , R. Rosset . J. Electroanal. Chem. , 1974 . 49 287 DOI: 10.1016/S0022-0728(74)80236-6 http://doi.org/10.1016/S0022-0728(74)80236-6 .

F. Allen , J. Howard , V. Hoy , G. Desiraju , D. Reddy , C. Wilson . J. Am. Chem. Soc. , 1996 . 118 4081 DOI: 10.1021/ja954057a http://doi.org/10.1021/ja954057a .

Jeffrey, G., “An introduction to hydrogen bonding”, Oxford University Press, 1977

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Synthesis and Characterization of D-/L-methionine Grafted PEDOTs for Selective Recognition of 3,4-Dihydroxyphenylalanine Enantiomers

DOI：10.1007/s10118-016-1772-x

摘要

Abstract

关键词

Keywords

references