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 Menu
Issue 10 (October) cover image

Export Article

Open AccessArticle
Molecules 2016, 21(10), 1297; doi:10.3390/molecules21101297

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
View Full-Text   |   Download PDF [9305 KB, uploaded 29 September 2016]   |  

Abstract

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
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

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.

Show more citation formats Show less citations formats

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

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top