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Kinetic Resolution of Racemic Mixtures via Enantioselective Photocatalysis

[Image: see text] Despite the increasing demand for enantiopure drugs in the pharmaceutical industry, currently available chiral separation technologies are still lagging behind, whether due to throughput or to operability considerations. This paper presents a new kinetic resolution method, based on...

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Autores principales: Arbell, Nitai, Bauer, Kesem, Paz, Yaron
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8397234/
https://www.ncbi.nlm.nih.gov/pubmed/34378379
http://dx.doi.org/10.1021/acsami.1c12216
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author Arbell, Nitai
Bauer, Kesem
Paz, Yaron
author_facet Arbell, Nitai
Bauer, Kesem
Paz, Yaron
author_sort Arbell, Nitai
collection PubMed
description [Image: see text] Despite the increasing demand for enantiopure drugs in the pharmaceutical industry, currently available chiral separation technologies are still lagging behind, whether due to throughput or to operability considerations. This paper presents a new kinetic resolution method, based on the specific adsorption of a target enantiomer onto a molecularly imprinted surface of a photocatalyst and its subsequent degradation through a photocatalytic mechanism. The current model system is composed of an active TiO(2) layer, on which the target enantiomer is adsorbed. A photocatalytic suppression layer of Al(2)O(3) is then grown around the adsorbed target molecules by atomic layer deposition. Following the removal of the templating molecules, molecularly imprinted cavities that correspond to the adsorbed species are formed. The stereospecific nature of these pores encourages enantioselective degradation of the undesired species through its enhanced adsorption on the photocatalyst surface, while dampening nonselective photocatalytic activity around the imprinted sites. The method, demonstrated with the dipeptide leucylglycine as a model system, revealed a selectivity factor of up to 7 and an enrichment of a single enantiomer to 85% from an initially racemic mixture. The wide range of parameters that can be optimized (photocatalyst, concentration of imprinted sites, type of passivating layer, etc.) points to the great potential of this method for obtaining enantiomerically pure compounds, beginning from racemic mixtures.
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spelling pubmed-83972342021-08-31 Kinetic Resolution of Racemic Mixtures via Enantioselective Photocatalysis Arbell, Nitai Bauer, Kesem Paz, Yaron ACS Appl Mater Interfaces [Image: see text] Despite the increasing demand for enantiopure drugs in the pharmaceutical industry, currently available chiral separation technologies are still lagging behind, whether due to throughput or to operability considerations. This paper presents a new kinetic resolution method, based on the specific adsorption of a target enantiomer onto a molecularly imprinted surface of a photocatalyst and its subsequent degradation through a photocatalytic mechanism. The current model system is composed of an active TiO(2) layer, on which the target enantiomer is adsorbed. A photocatalytic suppression layer of Al(2)O(3) is then grown around the adsorbed target molecules by atomic layer deposition. Following the removal of the templating molecules, molecularly imprinted cavities that correspond to the adsorbed species are formed. The stereospecific nature of these pores encourages enantioselective degradation of the undesired species through its enhanced adsorption on the photocatalyst surface, while dampening nonselective photocatalytic activity around the imprinted sites. The method, demonstrated with the dipeptide leucylglycine as a model system, revealed a selectivity factor of up to 7 and an enrichment of a single enantiomer to 85% from an initially racemic mixture. The wide range of parameters that can be optimized (photocatalyst, concentration of imprinted sites, type of passivating layer, etc.) points to the great potential of this method for obtaining enantiomerically pure compounds, beginning from racemic mixtures. American Chemical Society 2021-08-11 2021-08-25 /pmc/articles/PMC8397234/ /pubmed/34378379 http://dx.doi.org/10.1021/acsami.1c12216 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Arbell, Nitai
Bauer, Kesem
Paz, Yaron
Kinetic Resolution of Racemic Mixtures via Enantioselective Photocatalysis
title Kinetic Resolution of Racemic Mixtures via Enantioselective Photocatalysis
title_full Kinetic Resolution of Racemic Mixtures via Enantioselective Photocatalysis
title_fullStr Kinetic Resolution of Racemic Mixtures via Enantioselective Photocatalysis
title_full_unstemmed Kinetic Resolution of Racemic Mixtures via Enantioselective Photocatalysis
title_short Kinetic Resolution of Racemic Mixtures via Enantioselective Photocatalysis
title_sort kinetic resolution of racemic mixtures via enantioselective photocatalysis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8397234/
https://www.ncbi.nlm.nih.gov/pubmed/34378379
http://dx.doi.org/10.1021/acsami.1c12216
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