Colorimetric Recognition of 3,4-Dihydroxy-D,L-phenylalanine with Tetrapeptide-modified Copper Nanoparticles as Chiral Nanozymes

doi:10.1007/s40242-023-3193-z

高等学校化学研究 ›› 2023, Vol. 39 ›› Issue (6): 1092-1099.doi: 10.1007/s40242-023-3193-z

Colorimetric Recognition of 3,4-Dihydroxy-D,L-phenylalanine with Tetrapeptide-modified Copper Nanoparticles as Chiral Nanozymes

TIAN Lin^1,2, CHENG Cheng^1,3, ZHAO Zhenwen^1,4, LIU Wei², and QI Li^1,4

1. Beijing National Laboratory for Molecular Sciences, Key Laboratory of Analytical Chemistry for Living Biosystems, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P.R. China;
2. School of Pharmacy, Xinxiang Medical University, Xinxiang 453003, P.R. China;
3. College of Chemistry & Environmental Science, Hebei University, Baoding 071002, P.R. China;
4. School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P.R. China

收稿日期:2023-08-15 出版日期:2023-12-01 发布日期:2023-11-18
通讯作者: QI Li, LIU Wei E-mail:qili@iccas.ac.cn;liuwei@xxmu.edu.cn
基金资助:
This work was supported by the National Natural Science Foundation of China (No.22274159).

Colorimetric Recognition of 3,4-Dihydroxy-D,L-phenylalanine with Tetrapeptide-modified Copper Nanoparticles as Chiral Nanozymes

TIAN Lin^1,2, CHENG Cheng^1,3, ZHAO Zhenwen^1,4, LIU Wei², and QI Li^1,4

1. Beijing National Laboratory for Molecular Sciences, Key Laboratory of Analytical Chemistry for Living Biosystems, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P.R. China;
2. School of Pharmacy, Xinxiang Medical University, Xinxiang 453003, P.R. China;
3. College of Chemistry & Environmental Science, Hebei University, Baoding 071002, P.R. China;
4. School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P.R. China

Received:2023-08-15 Online:2023-12-01 Published:2023-11-18
Contact: QI Li, LIU Wei E-mail:qili@iccas.ac.cn;liuwei@xxmu.edu.cn
Supported by:
This work was supported by the National Natural Science Foundation of China (No.22274159).

摘要/Abstract

摘要： The construct of artificial nanocatalyts by simulating natural enzymes and thereby bringing new properties for practical applications is still a challenging task to date. In this study, chiral tetrapeptide (L-phenylalanine-L-phenylalanine-L-cysteine-L-histidine)-engineered copper nanoparticles (FFCH@CuNPs) were fabricated as an artificial peroxidase (POD). More interestingly, the nano-catalysts exhibited chiral identification function. In comparison with other nanocatalysts like L-cysteine-, L-histidine-, chiral dipeptide (L-cysteine-L-histidine)-, or chiral tripeptide (L-phenylalanine-L-cysteine-L-histidine)-modified CuNPs, FFCH@CuNPs demonstrated higher POD-mimetic catalytic activity in the 3,3',5,5'-tetramethylbenzidine (TMB)-H₂O₂ system and stronger enantioselectivity in the recognition of 3,4-dihydroxy-D,L-phenylalanine (D,L-DOPA) enantiomers. Considering the strength difference between the intermolecular hydrogen bonding and the π-π interactions, the principle behind the chiral discrimination of D,L-DOPA was explored. Furthermore, higher contents of surface Cu²⁺ ions and hydroxyl radicals were found in the FFCH@CuNPs-D-DOPA-TMB-H₂O₂ system than in the FFCH@CuNPs-L-DOPA-TMB-H₂O₂ system. Based on these results, a protocol for distinguishing between D,L-DOPA enantiomers through colorimetric recognition was established. This study provides a new insight into the design and fabrication of oligopeptides@CuNPs-based chiral nanozymes with improved catalytic performance and features additional to those of natural enzymes.

关键词: Chiral nanozyme, Copper nanoparticle, 3,4-Dihydroxy-D,L-phenylalanine (D,L-DOPA), Enantioselectivity, Tetrapeptide ligand

Abstract: The construct of artificial nanocatalyts by simulating natural enzymes and thereby bringing new properties for practical applications is still a challenging task to date. In this study, chiral tetrapeptide (L-phenylalanine-L-phenylalanine-L-cysteine-L-histidine)-engineered copper nanoparticles (FFCH@CuNPs) were fabricated as an artificial peroxidase (POD). More interestingly, the nano-catalysts exhibited chiral identification function. In comparison with other nanocatalysts like L-cysteine-, L-histidine-, chiral dipeptide (L-cysteine-L-histidine)-, or chiral tripeptide (L-phenylalanine-L-cysteine-L-histidine)-modified CuNPs, FFCH@CuNPs demonstrated higher POD-mimetic catalytic activity in the 3,3',5,5'-tetramethylbenzidine (TMB)-H₂O₂ system and stronger enantioselectivity in the recognition of 3,4-dihydroxy-D,L-phenylalanine (D,L-DOPA) enantiomers. Considering the strength difference between the intermolecular hydrogen bonding and the π-π interactions, the principle behind the chiral discrimination of D,L-DOPA was explored. Furthermore, higher contents of surface Cu²⁺ ions and hydroxyl radicals were found in the FFCH@CuNPs-D-DOPA-TMB-H₂O₂ system than in the FFCH@CuNPs-L-DOPA-TMB-H₂O₂ system. Based on these results, a protocol for distinguishing between D,L-DOPA enantiomers through colorimetric recognition was established. This study provides a new insight into the design and fabrication of oligopeptides@CuNPs-based chiral nanozymes with improved catalytic performance and features additional to those of natural enzymes.

Key words: Chiral nanozyme, Copper nanoparticle, 3,4-Dihydroxy-D,L-phenylalanine (D,L-DOPA), Enantioselectivity, Tetrapeptide ligand

TIAN Lin, CHENG Cheng, ZHAO Zhenwen, LIU Wei, and QI Li. Colorimetric Recognition of 3,4-Dihydroxy-D,L-phenylalanine with Tetrapeptide-modified Copper Nanoparticles as Chiral Nanozymes[J]. 高等学校化学研究, 2023, 39(6): 1092-1099.

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Colorimetric Recognition of 3,4-Dihydroxy-D,L-phenylalanine with Tetrapeptide-modified Copper Nanoparticles as Chiral Nanozymes

Colorimetric Recognition of 3,4-Dihydroxy-D,L-phenylalanine with Tetrapeptide-modified Copper Nanoparticles as Chiral Nanozymes

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