Voltammetric enantiomeric differentiation of tryptophan by using multiwalled carbon nanotubes functionalized with ferrocene and β-cyclodextrin

被引:72
作者
Niu, Xiaohui [1 ]
Yang, Xing [1 ]
Mo, Zunli [1 ]
Guo, Ruibin [1 ]
Liu, Nijuan [1 ]
Zhao, Pan [1 ]
Liu, Zhenyu [1 ]
Ouyang, Meixuan [1 ]
机构
[1] Northwest Normal Univ, Coll Chem & Chem Engn, Res Ctr Gansu Mil & Civilian Integrat Adv Struct, Minist Educ China,Key Lab Ecoenvironm Related Pol, Lanzhou 730070, Gansu, Peoples R China
基金
中国国家自然科学基金;
关键词
Electrochemical recognition; Chiral sensor; pi-pi stacking; Covalent crosslinking; Tryptophan enantiomers; ELECTROCHEMICAL ENANTIOSELECTIVE RECOGNITION; CHIRAL RECOGNITION; TETRACARBOXYLIC ACID; COMPOSITE; GRAPHENE; SENSOR; ENANTIORECOGNITION;
D O I
10.1016/j.electacta.2018.12.041
中图分类号
O646 [电化学、电解、磁化学];
学科分类号
081704 ;
摘要
Two types of ferrocene-functionalized multiwalled carbon nanotubes (MWCNTs) are described. The first was obtained by adsorption of ferrocene (Fc) on MWCNTs via pi-pi stacking and is referred to as Fc/MWCNTs. The second was prepared via a conjugation reaction between ferrocenecarboxylic acid and aminated MWCNTs to result on covalently modified MWCNTs referred to as MWCNT-Fc. MWCNT/Fc has a better conductivity than MWCNT-Fc. But electrochemical recognition results clearly showed the MWCNTs-Fc/beta-CD/GCE can exhibit better chiral recognition ability to tryptophan enantiomers than beta-CD/Fc/MWCNTs/GCE. By combining the merits of beta-cyclodextrin (beta-CD) and MWCNTs-Fc, an electrochemical sensor for L-tryptophan was obtained. Its characterizations by SEM, TEM, TGA, Raman spectroscopy and XPS showed that the Fc/MWCNTs and MWCNTs-Fc have successfully been synthesized. Enantioselective recognition was accomplished by differential pulse voltammetry. Tryptophan enantiomers can be differentiated with an enantioselectivity coefficient (I-D-T-rp/IL-Trp) of 5.78. Moreover, the chiral recognition mechanism of beta-CD recognition tryptophan enantiomers was proposed. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:650 / 659
页数:10
相关论文
共 39 条
[1]  
Alam A. U., 2018, Sensors and Actuators, B: Chemical, V254, P896, DOI DOI 10.1016/J.SNB.2017.07.127
[2]   Enhanced host-guest electrochemical recognition of dopamine using cyclodextrin in the presence of carbon nanotubes [J].
Alarcon-Angeles, G. ;
Perez-Lopez, B. ;
Palomar-Pardave, M. ;
Ramirez-Silva, M. T. ;
Alegret, S. ;
Merkoci, A. .
CARBON, 2008, 46 (06) :898-906
[3]   Chiral recognition mechanisms [J].
Berthod, A .
ANALYTICAL CHEMISTRY, 2006, 78 (07) :2093-2099
[4]   Enantioseparation by ultra-high-performance liquid chromatography [J].
Cavazzini, Alberto ;
Marchetti, Nicola ;
Guzzinati, Roberta ;
Pierini, Marco ;
Ciogli, Alessia ;
Kotoni, Dorina ;
D'Acquarica, Ilaria ;
Villani, Claudio ;
Gasparrini, Francesco .
TRAC-TRENDS IN ANALYTICAL CHEMISTRY, 2014, 63 :95-103
[5]   Electrochemical enantioselective recognition of tryptophane enantiomers based on chiral ligand exchange [J].
Chen, Qiao ;
Zhou, Juan ;
Han, Qian ;
Wang, Yonghua ;
Fu, Yingzi .
COLLOIDS AND SURFACES B-BIOINTERFACES, 2012, 92 :130-135
[6]   Chiral PEDOT-Based Enantioselective Electrode Modification Material for Chiral Electrochemical Sensing: Mechanism and Model of Chiral Recognition [J].
Dong, Liqi ;
Zhang, Youshan ;
Duan, Xuemin ;
Zhu, Xiaofei ;
Sun, Hui ;
Xu, Jingkun .
ANALYTICAL CHEMISTRY, 2017, 89 (18) :9695-9702
[7]   Electrochemical chiral recognition of tryptophan using a glassy carbon electrode modified with β-cyclodextrin and graphene [J].
Feng, Wanlian ;
Liu, Chao ;
Lu, Shaoyou ;
Zhang, Chuyi ;
Zhu, Xiaohua ;
Liang, Yong ;
Nan, Junmin .
MICROCHIMICA ACTA, 2014, 181 (5-6) :501-509
[8]   Chiral recognition of mandelic acid by L-phenylalanine-modified sensor using quartz crystal microbalance [J].
Guo, Hui-Shi ;
Kim, Jong-Min ;
Chang, Sang-Mok ;
Kim, Woo-Sik .
BIOSENSORS & BIOELECTRONICS, 2009, 24 (09) :2931-2934
[9]   Self-Healing Hydrogels of Low Molecular Weight Poly(vinyl alcohol) Assembled by Host-Guest Recognition [J].
Jia, Yong-Guang ;
Jin, Jiahong ;
Liu, Sa ;
Ren, Li ;
Luo, Juntao ;
Zhu, X. X. .
BIOMACROMOLECULES, 2018, 19 (02) :626-632
[10]   Aqueous self-assembly of SDS@2β-CD complexes: lamellae and vesicles [J].
Jiang, Lingxiang ;
Peng, Yu ;
Yan, Yun ;
Huang, Jianbin .
SOFT MATTER, 2011, 7 (05) :1726-1731