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Engineering Cyclodextrin Clicked Chiral Stationary Phase for High-Efficiency Enantiomer Separation

The separation of racemic molecules is of crucial significance not only for fundamental research but also for technical application. Enantiomers remain challenging to be separated owing to their identical physical and chemical properties in achiral environments. Chromatographic techniques employing...

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Autores principales: Tang, Jian, Zhang, Shapopeng, Lin, Yuzhou, Zhou, Jie, Pang, Limin, Nie, Xuemei, Zhou, Baojing, Tang, Weihua
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4530664/
https://www.ncbi.nlm.nih.gov/pubmed/26235204
http://dx.doi.org/10.1038/srep11523
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author Tang, Jian
Zhang, Shapopeng
Lin, Yuzhou
Zhou, Jie
Pang, Limin
Nie, Xuemei
Zhou, Baojing
Tang, Weihua
author_facet Tang, Jian
Zhang, Shapopeng
Lin, Yuzhou
Zhou, Jie
Pang, Limin
Nie, Xuemei
Zhou, Baojing
Tang, Weihua
author_sort Tang, Jian
collection PubMed
description The separation of racemic molecules is of crucial significance not only for fundamental research but also for technical application. Enantiomers remain challenging to be separated owing to their identical physical and chemical properties in achiral environments. Chromatographic techniques employing chiral stationary phases (CSPs) have been developed as powerful tools for the chiral analysis and preparation of pure enantiomers, most of which are of biological and pharmaceutical interests. Here we report our efforts in developing high-performance phenylcarbamated cyclodextrin (CD) clicked CSPs. Insights on the impact of CD functionalities in structure design are provided. High-efficiency enantioseparation of a range of aryl alcohols and flavanoids with resolution values (R(s)) over 10 were demonstrated by per(3-chloro-4-methyl)phenylcarbamated CD clicked CSP. Comparison study and molecular simulations suggest the improved enantioselectivity was attributed to higher interactions energy difference between the complexes of enantiomers and CSPs with phenylcarbamated CD bearing 3-chloro and 4-methyl functionalities.
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spelling pubmed-45306642015-08-11 Engineering Cyclodextrin Clicked Chiral Stationary Phase for High-Efficiency Enantiomer Separation Tang, Jian Zhang, Shapopeng Lin, Yuzhou Zhou, Jie Pang, Limin Nie, Xuemei Zhou, Baojing Tang, Weihua Sci Rep Article The separation of racemic molecules is of crucial significance not only for fundamental research but also for technical application. Enantiomers remain challenging to be separated owing to their identical physical and chemical properties in achiral environments. Chromatographic techniques employing chiral stationary phases (CSPs) have been developed as powerful tools for the chiral analysis and preparation of pure enantiomers, most of which are of biological and pharmaceutical interests. Here we report our efforts in developing high-performance phenylcarbamated cyclodextrin (CD) clicked CSPs. Insights on the impact of CD functionalities in structure design are provided. High-efficiency enantioseparation of a range of aryl alcohols and flavanoids with resolution values (R(s)) over 10 were demonstrated by per(3-chloro-4-methyl)phenylcarbamated CD clicked CSP. Comparison study and molecular simulations suggest the improved enantioselectivity was attributed to higher interactions energy difference between the complexes of enantiomers and CSPs with phenylcarbamated CD bearing 3-chloro and 4-methyl functionalities. Nature Publishing Group 2015-08-03 /pmc/articles/PMC4530664/ /pubmed/26235204 http://dx.doi.org/10.1038/srep11523 Text en Copyright © 2015, Macmillan Publishers Limited http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Tang, Jian
Zhang, Shapopeng
Lin, Yuzhou
Zhou, Jie
Pang, Limin
Nie, Xuemei
Zhou, Baojing
Tang, Weihua
Engineering Cyclodextrin Clicked Chiral Stationary Phase for High-Efficiency Enantiomer Separation
title Engineering Cyclodextrin Clicked Chiral Stationary Phase for High-Efficiency Enantiomer Separation
title_full Engineering Cyclodextrin Clicked Chiral Stationary Phase for High-Efficiency Enantiomer Separation
title_fullStr Engineering Cyclodextrin Clicked Chiral Stationary Phase for High-Efficiency Enantiomer Separation
title_full_unstemmed Engineering Cyclodextrin Clicked Chiral Stationary Phase for High-Efficiency Enantiomer Separation
title_short Engineering Cyclodextrin Clicked Chiral Stationary Phase for High-Efficiency Enantiomer Separation
title_sort engineering cyclodextrin clicked chiral stationary phase for high-efficiency enantiomer separation
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4530664/
https://www.ncbi.nlm.nih.gov/pubmed/26235204
http://dx.doi.org/10.1038/srep11523
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