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

DOI: 10.1002/chem.202100899 DOI Help

Authors: Lee Cronin (University of Glasgow) , Robert Pow (University of Glasgow) , Zoe Sinclair (University of Glasgow) , Nicola Bell (University of Glasgow) , Nancy Watfa (University of Glasgow) , Yousef Abul-Haija (University of Glasgow) , Deliang Long (University of Glasgow)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Chemistry – A European Journal

State: Published (Approved)
Published: July 2021
Diamond Proposal Number(s): 18953

Open Access Open Access

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.

Journal Keywords: Host-Guest Systems; Polyoxometalates; Chiral Recognition; NMR Spectroscopy; Amino Alcohols

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction


Discipline Tags:

Organic Chemistry Chemistry

Technical Tags:

Diffraction Single Crystal X-ray Diffraction (SXRD)