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Investigation of Temperature Cycling with Coupled Vessels for Efficient Deracemization of NMPA

[Image: see text] Chiral compounds can exist as pairs of nonsuperimposable stereoisomers (enantiomers) possessing the same physical properties but interacting differently with biological systems. This makes them interesting materials to be explored by the pharmaceutical and food industries. In this...

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Autores principales: Rehman, Ghufran ur, Vetter, Thomas, Martin, Philip A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10402294/
https://www.ncbi.nlm.nih.gov/pubmed/37547885
http://dx.doi.org/10.1021/acs.cgd.2c01138
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author Rehman, Ghufran ur
Vetter, Thomas
Martin, Philip A.
author_facet Rehman, Ghufran ur
Vetter, Thomas
Martin, Philip A.
author_sort Rehman, Ghufran ur
collection PubMed
description [Image: see text] Chiral compounds can exist as pairs of nonsuperimposable stereoisomers (enantiomers) possessing the same physical properties but interacting differently with biological systems. This makes them interesting materials to be explored by the pharmaceutical and food industries. In this study, to obtain pure enantiomers from their conglomerates, a method that involves using a two-vessel system for deracemization of N-(2-methylbenzylidene) phenylglycine amide (NMPA) was developed. In this method, a suspension was transferred with a pulsating pumping profile between two inter-connected stirred vessels that were set at constant temperatures. As the suspension was exposed to more rapid changes in temperature, it resulted in the speeding up of the process and thus enhancing productivity in comparison to a single vessel system. The results confirmed successful deracemization of NMPA. A modified pumping profile and tubing design eliminated the issue of clogging of the transfer tubes and ensured effective suspension transfer for longer durations. Operating parameters, such as initial enantiomeric excess, vessel residence time, and suspension density were also investigated. In this method, optimization of residence time was necessary to enhance the efficiency of the process further. Results confirmed that this methodology has the potential to be more adaptable and scalable as it involved no mechanical attrition.
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spelling pubmed-104022942023-08-05 Investigation of Temperature Cycling with Coupled Vessels for Efficient Deracemization of NMPA Rehman, Ghufran ur Vetter, Thomas Martin, Philip A. Cryst Growth Des [Image: see text] Chiral compounds can exist as pairs of nonsuperimposable stereoisomers (enantiomers) possessing the same physical properties but interacting differently with biological systems. This makes them interesting materials to be explored by the pharmaceutical and food industries. In this study, to obtain pure enantiomers from their conglomerates, a method that involves using a two-vessel system for deracemization of N-(2-methylbenzylidene) phenylglycine amide (NMPA) was developed. In this method, a suspension was transferred with a pulsating pumping profile between two inter-connected stirred vessels that were set at constant temperatures. As the suspension was exposed to more rapid changes in temperature, it resulted in the speeding up of the process and thus enhancing productivity in comparison to a single vessel system. The results confirmed successful deracemization of NMPA. A modified pumping profile and tubing design eliminated the issue of clogging of the transfer tubes and ensured effective suspension transfer for longer durations. Operating parameters, such as initial enantiomeric excess, vessel residence time, and suspension density were also investigated. In this method, optimization of residence time was necessary to enhance the efficiency of the process further. Results confirmed that this methodology has the potential to be more adaptable and scalable as it involved no mechanical attrition. American Chemical Society 2023-07-10 /pmc/articles/PMC10402294/ /pubmed/37547885 http://dx.doi.org/10.1021/acs.cgd.2c01138 Text en © 2023 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 Rehman, Ghufran ur
Vetter, Thomas
Martin, Philip A.
Investigation of Temperature Cycling with Coupled Vessels for Efficient Deracemization of NMPA
title Investigation of Temperature Cycling with Coupled Vessels for Efficient Deracemization of NMPA
title_full Investigation of Temperature Cycling with Coupled Vessels for Efficient Deracemization of NMPA
title_fullStr Investigation of Temperature Cycling with Coupled Vessels for Efficient Deracemization of NMPA
title_full_unstemmed Investigation of Temperature Cycling with Coupled Vessels for Efficient Deracemization of NMPA
title_short Investigation of Temperature Cycling with Coupled Vessels for Efficient Deracemization of NMPA
title_sort investigation of temperature cycling with coupled vessels for efficient deracemization of nmpa
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10402294/
https://www.ncbi.nlm.nih.gov/pubmed/37547885
http://dx.doi.org/10.1021/acs.cgd.2c01138
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