Next Article in Journal
Increasing the Level of IRS-1 and Insulin Pathway Sensitivity by Natural Product Carainterol A
Next Article in Special Issue
HPLC Separation of Diastereomers: Chiral Molecular Tools Useful for the Preparation of Enantiopure Compounds and Simultaneous Determination of Their Absolute Configurations
Previous Article in Journal
Antidermatophytic Action of Resorcinol Derivatives: Ultrastructural Evidence of the Activity of Phenylethyl Resorcinol against Microsporum gypseum
Previous Article in Special Issue
Preparation of Two New Diasteromeric Chiral Stationary Phases Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid and (R)- or (S)-1-(1-Naphthyl)ethylamine and Chiral Tethering Group Effect on the Chiral Recognition
Article

Mining Chromatographic Enantioseparation Data Using Matched Molecular Pair Analysis

1
Department of Structural Chemistry, Merck Research Laboratories, Rahway, NJ 07065, USA
2
Aix Marseille Université, Centrale Marseille, CNRS, iSm2, 13397 Marseille CEDEX 20, France
3
Department of Chemistry, University of Illinois, Urbana, IL 61801, USA
4
Department of Process Research & Development, Merck Research Laboratories, Rahway, NJ 07055, USA
*
Authors to whom correspondence should be addressed.
Academic Editor: Yoshio Okamoto
Received: 13 July 2016 / Revised: 14 September 2016 / Accepted: 16 September 2016 / Published: 29 September 2016
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. View Full-Text
Keywords: matched molecular pairs; chiral chromatography; chiral recognition matched molecular pairs; chiral chromatography; chiral recognition
Show Figures

Figure 1

MDPI and ACS Style

Sheridan, R.P.; Piras, P.; Sherer, E.C.; Roussel, C.; Pirkle, W.H.; Welch, C.J. Mining Chromatographic Enantioseparation Data Using Matched Molecular Pair Analysis. Molecules 2016, 21, 1297. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules21101297

AMA Style

Sheridan RP, Piras P, Sherer EC, Roussel C, Pirkle WH, Welch CJ. Mining Chromatographic Enantioseparation Data Using Matched Molecular Pair Analysis. Molecules. 2016; 21(10):1297. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules21101297

Chicago/Turabian Style

Sheridan, Robert P., Patrick Piras, Edward C. Sherer, Christian Roussel, William H. Pirkle, and Christopher J. Welch 2016. "Mining Chromatographic Enantioseparation Data Using Matched Molecular Pair Analysis" Molecules 21, no. 10: 1297. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules21101297

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop