Labuta, J;
Ishihara, S;
Sikorsky, T;
Futera, Z;
Shundo, A;
Hanykova, L;
Burda, JV;
... Hill, JP; + view all
(2013)
NMR spectroscopic detection of chirality and enantiopurity in referenced systems without formation of diastereomers.
Nature Communications
, 4
, Article 2188 (2013). 10.1038/ncomms3188.
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Abstract
Enantiomeric excess of chiral compounds is a key parameter that determines their activity or therapeutic action. The current paradigm for rapid measurement of enantiomeric excess using NMR is based on the formation of diastereomeric complexes between the chiral analyte and a chiral resolving agent, leading to (at least) two species with no symmetry relationship. Here we report an effective method of enantiomeric excess determination using a symmetrical achiral molecule as the resolving agent, which is based on the complexation with analyte (in the fast exchange regime) without the formation of diastereomers. The use of N,N′-disubstituted oxoporphyrinogen as the resolving agent makes this novel method extremely versatile, and appropriate for various chiral analytes including carboxylic acids, esters, alcohols and protected amino acids using the same achiral molecule. The model of sensing mechanism exhibits a fundamental linear response between enantiomeric excess and the observed magnitude of induced chemical shift non-equivalence in the 1H NMR spectra.
| Type: | Article |
|---|---|
| Title: | NMR spectroscopic detection of chirality and enantiopurity in referenced systems without formation of diastereomers |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1038/ncomms3188 |
| Publisher version: | https://doi.org/10.1038/ncomms3188 |
| Language: | English |
| Additional information: | Copyright © 2013 Macmillan Publishers Limited. All rights reserved. This work is licensed under a Creative Commons AttributionNonCommercial-NoDerivs 3.0 Unported License. To view a copy of this license, visit http://creativecommons.org/licenses/by-nc-nd/3.0/ |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10059862 |
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