Synthesis and characterization of D-/L-methionine grafted PEDOTs for selective recognition of 3,4-dihydroxyphenylalanine enantiomers

Dong, Liqi; Hu, Dufen; Duan, Xuemin; Wang, Zhi peng; Zhang, Kai Xin; Zhu, Xiaoxiao; Sun, Hui; Zhang, You shan; Xu, Jing

doi:10.1007/s10118-016-1772-x

Cited by 6 publications

(3 citation statements)

References 51 publications

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“…Poly(3,4-ethylenedioxythiophene) (PEDOT), one of the most stable and promising conducting polymers (CPs) available, has been employed for chemo/biosensors because of its high electrical conductivity, low bandgap, and outstanding environmental stability. − Therefore, chiral PEDOT is a promising electrode modification material for electrochemical chiral recognition. We previously reported the syntheses of various chiral substituted PEDOT species, such as chloromethyl-, l -leucine-, ( R )-/( S )-2-phenylpropionic acid-, and d -/ l -methionine-substituted PEDOT, by grafting a chiral moiety to a side-chain functionalized PEDOT (Scheme ). This common and effective synthesis strategy counterbalances the achirality of PEDOT.…”

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confidence: 99%

“…29−31 Therefore, chiral PEDOT is a promising electrode modification material for electrochemical chiral recognition. We previously reported the syntheses of various chiral substituted PEDOT species, such as chloromethyl-, 32 L-leucine-, 33 (R)-/(S)-2-phenylpropionic acid-, 34 and D-/ L-methionine-substituted PEDOT, 35 by grafting a chiral moiety to a side-chain functionalized PEDOT (Scheme 1). This common and effective synthesis strategy counterbalances the achirality of PEDOT.…”

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confidence: 99%

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Chiral PEDOT-Based Enantioselective Electrode Modification Material for Chiral Electrochemical Sensing: Mechanism and Model of Chiral Recognition

et al. 2017

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The development of electrochemical methods for enantioselective recognition is a focus of research in pharmaceuticals and biotechnology. In this study, a pair of water-soluble chiral 3,4-ethylenedioxythiophene (EDOT) derivatives, (R)-2'-hydroxymethyl-3,4-ethylenedioxythiophene ((R)-EDTM) and (S)-2'-hydroxymethyl-3,4-ethylenedioxythiophene ((S)-EDTM), were synthesized and electrodeposited on the surface of a glassy carbon electrode (GCE) via current-time (I-t) polymerization in an aqueous LiClO electrolyte. These chiral PEDOT polymers were used to fabricate chiral sensors and to investigate the enantioselective recognition of d-/l-3,4-dihydroxyphenylalanine, d-/l-tryptophan, and (R)-/(S)-propranolol enantiomers, respectively. The results indicated that the (R)-PEDTM/GCE sensor showed a higher peak current response toward the levo or (S) forms of the tested enantiomers, while the opposite phenomenon occurred for (S)-PEDTM/GCE. The mechanism of the stereospecific interaction between these enantiomers and the chiral polymers was determined. Therefore, a model of the chiral recognition by the chiral conducting polymer electrodes and an electrochemical method was proposed. The chirality of the enantiomers was confirmed by two parameters: the chirality of the electrode and the peak current response. These findings pave the way for the application of chiral PEDOT as electrode modification material in the electrochemical chiral recognition field.

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Chiral PEDOT-Based Enantioselective Electrode Modification Material for Chiral Electrochemical Sensing: Mechanism and Model of Chiral Recognition

et al. 2017

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“…Following the discovery of CPs, Alan J. Heeger, Alan G. MacDiarmid, and Hideki Shirakawa received the Nobel Prize for Chemistry in 2000 [96]. The CPs most frequently encountered in scientific research are PPy [97][98][99][100][101], PANI [102][103][104][105], PEDOT [46,[106][107][108][109], PT [110][111][112][113], and polyacetylene [114][115][116], the chemical structures of which are shown in Figure 3. This type of polymer is usually obtained by electrochemical polymerization, a process that takes place in a solution that includes the solvent, the polymerizable monomer, and the electrolyte.…”

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A Review of Sensors and Biosensors Modified with Conducting Polymers and Molecularly Imprinted Polymers Used in Electrochemical Detection of Amino Acids: Phenylalanine, Tyrosine, and Tryptophan

Dinu

Apetrei

2022

IJMS

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Recently, the studies on developing sensors and biosensors—with an obvious interdisciplinary character—have drawn the attention of many researchers specializing in various fundamental, but also complex domains such as chemistry, biochemistry, physics, biophysics, biology, bio-pharma-medicine, and bioengineering. Along these lines, the present paper is structured into three parts, and is aimed at synthesizing the most relevant studies on the construction and functioning of versatile devices, of electrochemical sensors and biosensors, respectively. The first part presents examples of the most representative scientific research focusing on the role and the importance of the phenylalanine, tyrosine, and tryptophan amino acids, selected depending on their chemical structure and their impact on the central nervous system. The second part is dedicated to presenting and exemplifying conductor polymers and molecularly imprinted polymers used as sensitive materials in achieving electrochemical sensors and biosensors. The last part of the review analyzes the sensors and biosensors developed so far to detect amino acids with the aid of conductor polymers and molecularly imprinted polymers from the point of view of the performances obtained, with emphasis on the detection methods, on the electrochemical reactions that take place upon detection, and on the electroanalytical performances. The present study was carried out with a view to highlighting, for the benefit of specialists in medicine and pharmacy, the possibility of achieving and purchasing efficient devices that might be used in the quality control of medicines, as well as in studying and monitoring diseases associated with these amino acids.

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Optically active helical polyisocyanides bearing chiral phosphine pendants: Facile synthesis and application in enantioselective Rauhut-Currier reaction

et al. 2017

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Synthesis and characterization of D-/L-methionine grafted PEDOTs for selective recognition of 3,4-dihydroxyphenylalanine enantiomers

Cited by 6 publications

References 51 publications

Chiral PEDOT-Based Enantioselective Electrode Modification Material for Chiral Electrochemical Sensing: Mechanism and Model of Chiral Recognition

Chiral PEDOT-Based Enantioselective Electrode Modification Material for Chiral Electrochemical Sensing: Mechanism and Model of Chiral Recognition

A Review of Sensors and Biosensors Modified with Conducting Polymers and Molecularly Imprinted Polymers Used in Electrochemical Detection of Amino Acids: Phenylalanine, Tyrosine, and Tryptophan

Optically active helical polyisocyanides bearing chiral phosphine pendants: Facile synthesis and application in enantioselective Rauhut-Currier reaction

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