Abstract
In this work, an electrochemical chiral sensor of a nanowire-like chiral metal-organic framework/multiwalled carbon nanotube-chitosan/glassy carbon electrode(D-MOF/MWCNTs-CS/GCE) was proposed for the enantiorecognition of L/D-tryptophan(L/D-Trp). The asymmetrical spatial structure of D-MOF provides the feasibility for the enantiorecognition of Trp enantiomers. Moreover, differential pulse voltammetry(DPV) was carried out to be the detection method and the DPV peak potential difference(ΔEp) between L-Trp and D-Trp was referred as the index of the enantiorecognition performance. Several parameters, such as mass ratios and drop-coated volume of MWCNTs-CS, drop-coated volume and concentration of D-MOF, pH and detection temperature of D-MOF/MWCNTs-CS/GCE were optimized for the largest ΔEp value. And the molecular dynamics(MD) simulation was used to elucidate the enantiorecognition mechanism. Furthermore, the proportions of D-Trp(D-Trp%) in Trp mixtures were detected in a good linear relationship with the DPV peak potentials(Ep), and the proposed electrochemical chiral sensor exhibited good reproducibility, stability and enantiorecognition ability. Additionally, the proposed electrochemical chiral sensor(D-MOF/MWCNTs-CS/GCE) has a good application prospect in the fields of biomedicine, clinical diagnosis, chemical production, pharmaceuticals safety and so on.
Similar content being viewed by others
References
Eda G., Haluk B., Erhan Z., J. Pharmaceut. Biomed., 2022, 221, 115031
Zhao Y., Zhang Y., Liu H. L., Sun B. G., Anal. Bioanal. Chem., 2022, 414, 4885
Hamase K., Morikawa A., Zaitsu K., J. Chromatogr. B, 2002, 781, 73
Fuchs S., Berger R., Klomp L., Koning T., Mol. Genet. Metab., 2005, 85, 168
Zhou H., Ran G., Masson J., Wang C., Zhao Y., Song Q., Anal. Chem., 2018, 90, 3374
Hou H. P., Tang S. S., Liu Y. Q., Wang W., Liang A. X., Sun L. Q., Luo A. Q., J. Electroanal. Chem., 2022, 904, 115921
Guo L. J., Zhang Q., Huang Y. H., Han Q., Wang Y. H., Fu Y. Z., Bioelectrochemistry, 2013, 94, 87
Niu X. H., Yang X., Mo Z. L., Wang J., Pan Z., Liu Z. Y., Shui C., Liu G. G., Liu N. J., Guo R. B., Bioelectrochemistry, 2020, 131, 107396
Chinta J. P., Sensors Actuat. B: Chem., 2017, 248, 733
Wang C., Zhang L., Li X., Yu A., Zhang S., Talanta, 2020, 218, 121155
Chi Z. M., Li M. M., Xu J., Yang L., Anal. Bioanal. Chem., 2022, 414, 1641
Zou J., Zhao G. Q., Zhao G. L., Yu J. G., Coordin. Chem. Rev., 2022, 471, 214732
Guo J. L., Wei X. F., Lian H. T., Li L. S., Sun X. Y., Liu B., ACS Appl. Nano Mater., 2020, 3, 3675
Sun X. Z., Fu Z. B., Zhang M., Fu H., Lin C. H., Kuang J. J., Zhang H. Y., Hu P., Microchem. J., 2022, 183, 108074
Niu X. H., Yan S., Chen J. L., Li H. X., Wang K. J., Electrochim. Acta, 2020, 405, 139809
Dong L. Q., Zhang Y. S., Duan X. M., Zhu X. F., Sun H., Xu J. K., Anal. Chem., 2017, 89, 9695
Sun Y. X., Zhang D. D., Sheng Y., Xu D., Zhang R., Bradley M., Anal. Methods, 2021, 13, 2011
Liu N., Liu J., Niu X. H., Wang J., Guo R., Mo Z., Microchim. Acta, 2021, 188
He S., Shang X., Lu W., Tian Y., Xu Z., Zhang W., Anal. Chim. Acta, 2021, 1147, 155
Niu X., Yang X., Mo Z., Wang J., Pan Z., Liu Z., Shui C., Liu G., Liu N., Guo R., Bioelectrochemistry, 2020, 131, 107396
Yang X., Niu X., Mo Z., Guo R., Liu N., Zhao P., Liu Z., Microchim. Acta, 2019, 186, 333
Niu X., Yang X., Mo Z., Liu N., Guo R., Pan Z., Liu Z., Microchim. Acta, 2019, 186, 557
Bao L., Chen X., Yang B., Tao Y., Kong Y., ACS Appl. Mater. Inter., 2016, 8, 21710
Gong L., Zhao Q., Wu S., Yin Z., Wu D., Cai W., Kong Y., Langmuir, 2021, 37, 14454
Gong T., Zhu S., Huang S., Gu P., Xiong Y., Zhang J., Jiang X., Anal. Chim. Acta, 2022, 1191, 339276
Tao Y., Gu X., Yang B., Deng L., Bao L., Kong Y., Chu F., Qin Y., Anal. Chem., 2017, 89, 1900
Niu X., Yang X., Li H., Shi Q., Wang K., Chirality, 2021, 33, 248
Zou J., Yu J. G., Materials Science and Engineering: C, 2020, 112, 110910
Kuppler R. J., Timmons D. J., Fang Q. R., Li J. R., Makal T., Young M., Yuan D. Q., Zhao D., Zhuang W. J., Zhou H. C., Coord Chem Rev, 2009, 252, 3042
Liu Y. L., Zhao X. J., Yang X. X., Li Y. F., Analyst, 2013, 138, 4526
Yu L. Q., Yan X. P, Chem. Commun, 2013, 49, 2142
José N. S., Ana A. G., Yolanda M. M., Daniel R. S., Dmytro A., Pilar C. F., Matthew J. R., Carlos M. G., J. Am. Chem. Soc, 2017, 139, 4294
Bagheri N., Khataee A., Habibi B., Javad H., Talanta, 2018, 179, 710
Lee E., Ju H., Jung J. H., Ikeda M., Habata Y., Lee S. S., Inorg. Chem, 2019, 58, 1177
Bard A. J., Faulkne L. R., Electrochemical Methods Fundamentals and Application, John Wiley& Sons, New York, 2001
Patel B. R., Imran S., Ye W. Y., Weng H. Y., Noroozifar M., Kerman K, Electrochim. Acta, 2020, 362, 137094
Ou J., Tao Y. X., Xue J. J., Kong Y., Dai J. Y., Deng L. H., Electrochem. Commun., 2015, 57, 5
Yu Y., Tao Y. X., Yang B. Z., Wu D. T., Qin Y., Kong Y., Anal. Chem., 2017, 89, 12930
Hou H. P., Tang S. S., Wang W., Liu M., Liang A. X., Sun L. Q., Luo A. Q., J. Electrochem. Soc., 2022, 169, 037506
Gong T., Zhu S., Huang S. Q., Gu P. C, Xiong Y., Zhang J., Jiang X. H., Anal. Chim. Acta, 2022, 1191, 339276
He S. Y., Shang X., Lu W., Yang T., Xu Z. A., Zhang W., Anal. Chim. Acta, 2021, 1147, 155e164
Wang L. L., Gong W. C., Wang F., Yu Z. Y., Chen Z. L., Methods, 2016, 8, 3481e3487
Acknowledgements
This work was supported by the National Key R&D Program of China (No. 2019YFA0904104).
The authors thank Biological & Medical Engineering Core Facilities, Beijing Institute of Technology for kindly providing the laboratory facilities for testing. Moreover, the authors thank Chengdu Tianji Technology Co., Ltd. for their technical support in the construction of the molecular dynamics(MD) simulation.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
The authors declare no conflicts of interest.
Electronic Supplementary Material (ESM)
Rights and permissions
About this article
Cite this article
Hou, H., Tang, S., Wang, W. et al. Electrochemical Chiral Recognizing Tryptophan Enantiomers Based on Chiral Metal-Organic Framework D-MOF. Chem. Res. Chin. Univ. 39, 976–984 (2023). https://doi.org/10.1007/s40242-023-3004-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s40242-023-3004-6