l-Pyroglutamic Acid-Modified CdSe/ZnS Quantum Dots: A New Fluorescence-Responsive Chiral Sensing Platform for Stereospecific Molecular Recognition

Stereoselective recognition of amino acids is extremely important due to its high chirality-dependent interactions and physiological activities in life activities. We herein report a novel functionalized chiral fluorescent nanosensor prepared from surface modification of CdSe/ZnS quantum dots (QDs)...

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Bibliographic Details
Published in:Analytical chemistry (Washington) 2020-09, Vol.92 (17), p.12040-12048
Main Authors: Zhu, Fawei, Wang, Jing, Xie, Siqi, Zhu, Yuqiu, Wang, Lumin, Xu, Jinju, Liao, Sen, Ren, Jiwei, Liu, Qi, Yang, Hua, Chen, Xiaoqing
Format: Article
Language:English
Subjects:
Amino acids
Analytical chemistry
Cadmium selenides
Chemistry
Chirality
Density functional theory
Dihydroxyphenylalanine
Enantiomers
Fluorescence
Histidine
Hydrogen bonding
Modules
Pyroglutamic acid
Quantum dots
Recognition
Stereoselectivity
Zinc sulfide
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Summary:Stereoselective recognition of amino acids is extremely important due to its high chirality-dependent interactions and physiological activities in life activities. We herein report a novel functionalized chiral fluorescent nanosensor prepared from surface modification of CdSe/ZnS quantum dots (QDs) with pyroglutamic acid derivatives, which could serve as a chiral recognition module for fluorescence detection of chiral molecules. The sensor exhibited a unique stereoselective fluorescence response to histidine (His), glutamate (Glu), and dihydroxyphenylalanine (Dopa) and had preferable response performance to l-enantiomers. The enantiomeric fluorescence difference ratios of His, Glu, and Dopa enantiomers were 3.90, 3.40, and 2.49, respectively. The mechanism for the enantiomeric fluorescence recognition was systematically studied through a fluorescence spectrum, fluorescence life, and density functional theory (DFT) calculation. Presumably, the different hydrogen bonding capacity of the chiral recognition module with two enantiomers mainly contributed to the difference in fluorescence signals. As a result, a broader application of the pyroglutamic acid derivative-coated QDs as a fluorescence-responsive chiral sensing platform for enantiomeric detection would be expected.
ISSN:0003-2700
1520-6882
DOI:10.1021/acs.analchem.0c02668