We apply matched molecular pair (MMP) analysis to data from ChirBase, which contains literature reports of chromatographic enantioseparations. For the 19 chiral stationary phases we examined, we were able to identify 289 sets of pairs where there is a statistically significant and consistent difference in enantioseparation due to a small chemical change. In many cases these changes highlight enantioselectivity differences between pairs or small families of closely related molecules that have for many years been used to probe the mechanisms of chromatographic chiral recognition; for example, the comparison of N-H vs. N-Me analytes to determine the criticality of an N-H hydrogen bond in chiral molecular recognition. In other cases, statistically significant MMPs surfaced by the analysis are less familiar or somewhat puzzling, sparking a need to generate and test hypotheses to more fully understand. Consequently, mining of appropriate datasets using MMP analysis provides an important new approach for studying and understanding the process of chromatographic enantioseparation.
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http://dx.doi.org/10.3390/molecules21101297 | DOI Listing |
Biomed Chromatogr
February 2025
Department of Pharmaceutical Chemistry and Analysis, ISF College of Pharmacy, Moga, Punjab, India.
Enantioseparation and enantiorecognition are crucial in the pharmaceutical analysis of chiral substances, impacting safety, efficacy, and regulatory compliance. Enantioseparation refers to the process of separating enantiomers from a mixture, typically achieved through chromatography techniques like HPLC and SFC. In contrast, enantiorecognition involves the identification of enantiomers based on their interaction with a chiral selector without the need for separation.
View Article and Find Full Text PDFJ Sep Sci
December 2024
College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming, China.
Chiral macrocycles have emerged as attractive media for chromatographic enantioseparation due to their excellent host-guest recognition properties. In this study, a new chiral stationary phase (CSP) based on 1,1'-binaphthyl chiral polyimine macrocycle (CPM) was reported. The CPM was synthesized by one-step aldehyde-amine condensation of (S)-2,2'-dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxaldehyde with 1,2-phenylenediamine and bonded on thiolated silica via the thiol-ene click reaction to afford the CSP.
View Article and Find Full Text PDFBiomed Chromatogr
January 2025
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, India.
Biomed Chromatogr
January 2025
Univ. Lille, Inserm, Lille, France.
Anal Chim Acta
November 2024
Department of Chemistry and Biochemistry, The University of Texas at Arlington, USA. Electronic address:
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