S‐Click Reaction for Isotropic Orientation of Oxidases on Electrodes to Promote Electron Transfer at Low Potentials

Electrochemical sensors are essential for point‐of‐care testing (POCT) and wearable sensing devices. Establishing an efficient electron transfer route between redox enzymes and electrodes is key for converting enzyme‐catalyzed reactions into electrochemical signals, and for the development of robust...

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Published in:Angewandte Chemie International Edition 2019-11, Vol.58 (46), p.16480-16484
Main Authors: Xia, Lin, Han, Ming‐Jie, Zhou, Lu, Huang, Aiping, Yang, Zhaoya, Wang, Tianyuan, Li, Fahui, Yu, Lu, Tian, Changlin, Zang, Zhongsheng, Yang, Qing‐Zheng, Liu, Chenli, Hong, Wenxu, Lu, Yi, Alfonta, Lital, Wang, Jiangyun
Format: Article
Language:English
Subjects:
Amino acids
Biosensors
Chemical reactions
Chemical sensors
Electrochemistry
Electrodes
Electron transfer
Electrons
Enzymes
genetic code expansion
Propionic acid
Sensors
Tryptophan
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Summary:Electrochemical sensors are essential for point‐of‐care testing (POCT) and wearable sensing devices. Establishing an efficient electron transfer route between redox enzymes and electrodes is key for converting enzyme‐catalyzed reactions into electrochemical signals, and for the development of robust, sensitive, and selective biosensors. We demonstrate that the site‐specific incorporation of a novel synthetic amino acid (2‐amino‐3‐(4‐mercaptophenyl)propanoic acid) into redox enzymes, followed by an S‐click reaction to wire the enzyme to the electrode, facilitates electron transfer. The fabricated biosensor demonstrated real‐time and selective monitoring of tryptophan (Trp) in blood and sweat samples, with a linear range of 0.02–0.8 mm. Further developments along this route may result in dramatic expansion of portable electrochemical sensors for diverse health‐determination molecules. Blood, sweat & Trp: Electrochemical sensors are essential for point‐of‐care testing and wearable sensing devices. Efficient electron transfer from a redox enzyme to an electrode is established by wiring the two together with S‐click chemistry. These biosensors are sensitive and selective for tryptophan and glycine in blood and sweat. Key: l‐tryptophan oxidase (TrpOx), boron‐dipyrromethene (Bodipy), reduced semiquinone in flavoprotein (FAD⋅).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201909203