Enantioselective Recognition of Racemic Amino Alcohols in Aqueous Solution by Chiral Metal-Oxide Keplerate {Mo 132 } Cluster Capsules.

Autor: Pow RW; Department of Chemistry, University of Glasgow, University Avenue, Glasgow, G12 8QQ, UK., Sinclair ZL; Department of Chemistry, University of Glasgow, University Avenue, Glasgow, G12 8QQ, UK., Bell NL; Department of Chemistry, University of Glasgow, University Avenue, Glasgow, G12 8QQ, UK., Watfa N; Department of Chemistry, University of Glasgow, University Avenue, Glasgow, G12 8QQ, UK., Abul-Haija YM; Department of Chemistry, University of Glasgow, University Avenue, Glasgow, G12 8QQ, UK., Long DL; Department of Chemistry, University of Glasgow, University Avenue, Glasgow, G12 8QQ, UK., Cronin L; Department of Chemistry, University of Glasgow, University Avenue, Glasgow, G12 8QQ, UK.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2021 Aug 25; Vol. 27 (48), pp. 12327-12334. Date of Electronic Publication: 2021 Jul 30.
DOI: 10.1002/chem.202100899
Abstrakt: Determining the relative configuration or enantiomeric excess of a substance may be achieved using NMR spectroscopy by employing chiral shift reagents (CSRs). Such reagents interact noncovalently with the chiral solute, resulting in each chiral form experiencing different magnetic anisotropy; this is then 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, a set of chiral Keplerate host molecules has been synthesised. By exploiting the interactions of analyte molecules at the surface pores, the relative configuration of chiral amino alcohol guests (phenylalaninol and 2-amino-1-phenylethanol) in aqueous solvent was establish and their enantiomeric excess was determined by 1 H NMR using shifts of ΔΔδ=0.06 ppm. The use of POMs as chiral shift reagents represents an application of a class that is yet to be well established and opens avenues into aqueous host-guest chemistry with self-assembled recognition agents.
(© 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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