Enantioselective recognition of racemic amino alcohols in aqueous solution by chiral metal-oxide keplerate {Mo132} cluster capsules

Pow, R. W., Sinclair, Z. L., Bell, N. L. , Watfa, N., Abul-Haija, Y. M. , Long, D.-L. and Cronin, L. (2021) Enantioselective recognition of racemic amino alcohols in aqueous solution by chiral metal-oxide keplerate {Mo132} cluster capsules. Chemistry: A European Journal, 27(48), pp. 12327-12334. (doi: 10.1002/chem.202100899) (PMID:34196438)

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Abstract

Determining the relative configuration or enantiomeric excess of a substance may be achieved using NMR spectroscopy by employing chiral shift reagents (CSRs). Such reagents non-covalently interact with the chiral solute, resulting in each chiral form experiencing different magnetic anisotropy, which is reflected in their NMR spectra. The Keplerate polyoxometalate (POM) is a molybdenum-based, water-soluble, discrete inorganic structure with a pore-accessible inner cavity, decorated by differentiable ligands. Through ligand exchange from the self-assembled nanostructure we have synthesized a set of chiral Keplerate host molecules. By exploiting interactions of analyte molecules at the surface pores we establish the relative configuration of chiral amino alcohol guests (phenylalaninol and 2-amino-1-phenylethanol) in aqueous solvent and determine their enantiomeric excess by 1 H NMR. The use of POMs as chiral shift reagents represents an application of the class that is yet to be well established and opens avenues into aqueous host-guest chemistry with self-assembled recognition agents.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Long, Dr Deliang and Watfa, Dr Nancy and Sinclair, Ms Zoe and Pow, Mr Robert William and Abul-Haija, Yousef and Bell, Dr Nicola and Cronin, Professor Lee
Authors: Pow, R. W., Sinclair, Z. L., Bell, N. L., Watfa, N., Abul-Haija, Y. M., Long, D.-L., and Cronin, L.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Chemistry: A European Journal
Publisher:Wiley
ISSN:0947-6539
ISSN (Online):1521-3765
Published Online:01 July 2021
Copyright Holders:Copyright © 2021 The Authors
First Published:First published in Chemistry - A European Journal 27(48): 12327-12334
Publisher Policy:Reproduced under a Creative Commons License

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