Efficient monitoring of chiral information of bioactive compounds has gained considerable attention, due to their involvement in different biochemical processes. In this work, we propose a novel dynamic system for the easy and straightforward recognition of chiral redox active molecules and its possible use for the efficient measurement of enantiomeric excess in solution. The approach is based on the synergy between the localized enantioselective oxidation of only one of the two antipodes of a chiral molecule and the produced charge-compensating asymmetric proton flux along a bipolar electrode. The resulting clockwise or anticlockwise rotation is triggered only when the probe with the right chirality is present in solution. The angle of rotation shows a linear correlation with the analyte concentration, enabling the quantification of enantiomeric ratios in mixtures where the two antipodes are present in solution. This device was successfully used to simultaneously measure different ratios of the enantiomers of 3,4-dihydroxyphenylalanine and tryptophan. The versatility of the proposed approach opens up the possibility to use such a dynamic system as a straightforward (bio)analytical tool for the qualitative and quantitative discrimination of different redox active chiral probes.

Bipolar electrochemical rotors for the direct transduction of molecular chiral information / S. Arnaboldi, G. Salinas, G. Bonetti, R. Cirilli, T. Benincori, A. Kuhn. - In: BIOSENSORS & BIOELECTRONICS. - ISSN 0956-5663. - 218:(2022 Dec 15), pp. 114740.1-114740.6. [10.1016/j.bios.2022.114740]

Bipolar electrochemical rotors for the direct transduction of molecular chiral information

S. Arnaboldi
Primo
;
2022

Abstract

Efficient monitoring of chiral information of bioactive compounds has gained considerable attention, due to their involvement in different biochemical processes. In this work, we propose a novel dynamic system for the easy and straightforward recognition of chiral redox active molecules and its possible use for the efficient measurement of enantiomeric excess in solution. The approach is based on the synergy between the localized enantioselective oxidation of only one of the two antipodes of a chiral molecule and the produced charge-compensating asymmetric proton flux along a bipolar electrode. The resulting clockwise or anticlockwise rotation is triggered only when the probe with the right chirality is present in solution. The angle of rotation shows a linear correlation with the analyte concentration, enabling the quantification of enantiomeric ratios in mixtures where the two antipodes are present in solution. This device was successfully used to simultaneously measure different ratios of the enantiomers of 3,4-dihydroxyphenylalanine and tryptophan. The versatility of the proposed approach opens up the possibility to use such a dynamic system as a straightforward (bio)analytical tool for the qualitative and quantitative discrimination of different redox active chiral probes.
Bipolar electrochemistry; Chiral recognition; Inherently chiral oligomers; Rotors;
Settore CHIM/01 - Chimica Analitica
HE_ERC22SARNA_01 - Cargo-towing Highly enantioselective Electro-pumps: unconventional asymmetrIc Readout and transmission of chiral information (CHEIR) - ARNABOLDI, SERENA - Horizon Europe - European Research Council (ERC) - 2022
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/945192
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