A chiral helical self-assembly for electrochemical recognition of tryptophan enantiomers

Jiapei Yang; Datong Wu; Gao-Chao Fan; Linzheng Ma; Yongxin Tao; Yong Qin; Yong Kong

Electrochemistry Communications (Jul 2019)

A chiral helical self-assembly for electrochemical recognition of tryptophan enantiomers

Jiapei Yang,
Datong Wu,
Gao-Chao Fan,
Linzheng Ma,
Yongxin Tao,
Yong Qin,
Yong Kong

Affiliations

Jiapei Yang: Jiangsu Key Laboratory of Advanced Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China
Datong Wu: Jiangsu Key Laboratory of Advanced Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China
Gao-Chao Fan: Key Laboratory of Optic-electric Sensing and Analytical Chemistry for Life Science, MOE, Shandong Key Laboratory of Biochemical Analysis, Qingdao University of Science and Technology, Qingdao 266042, China
Linzheng Ma: College of Chemical and Environmental Engineering, Shandong University of Science and Technology, Qingdao 266590, China
Yongxin Tao: Jiangsu Key Laboratory of Advanced Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China
Yong Qin: Jiangsu Key Laboratory of Advanced Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China
Yong Kong: Jiangsu Key Laboratory of Advanced Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China; Corresponding author.

Journal volume & issue: Vol. 104

Abstract

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Molecular self-assembly has been regarded as a promising strategy for the construction of chiral sensing devices. Here, (1R,2R)-N,N-didodecylcyclohexane-1,2-dicarboxamide (DDC) was synthesized and then self-assembled in alcohol, and a chiral helical structure could be formed owing to the intermolecular hydrogen bond and the polarity effect of solvent. The chirality of the resultant helical self-assembly was confirmed by circular dichroism (CD) spectra, and then the chiral helical self-assembly was used for electrochemical recognition of tryptophan (Trp) enantiomers. Due to the higher affinity of the self-assembly toward L-Trp than D-Trp, which was revealed by hydrophilicity evaluation, efficient recognition of the Trp enantiomers (IL-Trp/ID-Trp = 8.74) was achieved. Keywords: Chirality, Self-assembly, Chiral helical structure, Electrochemical recognition, Tryptophan enantiomers

Published in Electrochemistry Communications

ISSN: 1388-2481 (Print); 1873-1902 (Online)
Publisher: Elsevier
Country of publisher: United States
LCC subjects: Technology: Chemical technology: Industrial electrochemistry; Science: Chemistry
Website: https://www.journals.elsevier.com/electrochemistry-communications

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