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

Tang J, Zhang S, Lin Y, Zhou J, Pang L, Nie X, Zhou B, Tang W - Sci Rep (2015)

Bottom Line: 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 (Rs) 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.

View Article: PubMed Central - PubMed

Affiliation: 1] Key Laboratory of Soft Chemistry and Functional Materials (Ministry of Education), Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China [2] Key Laboratory of Soft Chemistry and Functional Materials (Ministry of Education), Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China.

ABSTRACT
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 (Rs) 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.

No MeSH data available.


Related in: MedlinePlus

Click synthesis of perphenylcarbamated CD mono-clicked CSPs.
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f2: Click synthesis of perphenylcarbamated CD mono-clicked CSPs.

Mentions: The click preparation of CD CSP was conducted according to the reported protocol22. Starting from mono-6A-azido-β-CD 128, mono-6A-azido-per(3-chloro-4-methyl)phenylcarbamated β-CD 2a (or mono-6A-azido-per(3-methyl-4-chloro)phenylcarbamated β-CD 2b) was prepared as a key intermdiate compound, which was further immobilized onto alkynyl functionalized silica gel 322 via “click” chemistry to afford the CCC3M4-CSP (or CCM3C4-CSP) over 90% yield (Fig. 2). CCP-CSP was also prepared as reference12.


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

Tang J, Zhang S, Lin Y, Zhou J, Pang L, Nie X, Zhou B, Tang W - Sci Rep (2015)

Click synthesis of perphenylcarbamated CD mono-clicked CSPs.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4530664&req=5

f2: Click synthesis of perphenylcarbamated CD mono-clicked CSPs.
Mentions: The click preparation of CD CSP was conducted according to the reported protocol22. Starting from mono-6A-azido-β-CD 128, mono-6A-azido-per(3-chloro-4-methyl)phenylcarbamated β-CD 2a (or mono-6A-azido-per(3-methyl-4-chloro)phenylcarbamated β-CD 2b) was prepared as a key intermdiate compound, which was further immobilized onto alkynyl functionalized silica gel 322 via “click” chemistry to afford the CCC3M4-CSP (or CCM3C4-CSP) over 90% yield (Fig. 2). CCP-CSP was also prepared as reference12.

Bottom Line: 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 (Rs) 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.

View Article: PubMed Central - PubMed

Affiliation: 1] Key Laboratory of Soft Chemistry and Functional Materials (Ministry of Education), Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China [2] Key Laboratory of Soft Chemistry and Functional Materials (Ministry of Education), Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China.

ABSTRACT
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 (Rs) 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.

No MeSH data available.


Related in: MedlinePlus