Enantioselective resolution of two model amino acids using inherently chiral oligomer films with uncorrelated molecular structures

Preferential crystallization induced by chiral surfaces is an interesting alternative to isolate enantiopure antipodes. Herein, we take advantage of the outstanding enantiorecognition capabilities of inherently chiral oligomers to induce an enantioselective crystallization process. We exemplify this...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2023-08, Vol.59 (64), p.9758-9761
Main Authors: Nulek, Thitapond, Arnaboldi, Serena, Salinas, Gerardo, Bonetti, Giorgia, Cirilli, Roberto, Benincori, Tiziana, Wattanakit, Chularat, Flood, Adrian E, Kuhn, Alexander
Format: Article
Language:English
Subjects:
Amino acids
Crystallization
Enantiomers
Glutamic acid
Molecular structure
Oligomers
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Summary:Preferential crystallization induced by chiral surfaces is an interesting alternative to isolate enantiopure antipodes. Herein, we take advantage of the outstanding enantiorecognition capabilities of inherently chiral oligomers to induce an enantioselective crystallization process. We exemplify this strategy with two amino acid model molecules, asparagine and glutamic acid, having a completely uncorrelated structure with respect to the template. This illustrates the versatility of the approach with potential applications in the resolution of pharmaceutical compounds. Chiral oligomers are proposed as templates for the chiral resolution of amino acids. High enantiomeric excess is achieved when they are employed as surfaces with electrochemically tunable hydrophilicity, despite their uncorrelated molecular structure.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc02258g