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Chiral encoded metals for enantioselective synthesis of pharmaceuticals and recognition of chiral amino acids

Authors
  • Suwankaisorn, Banyong
Publication Date
Dec 04, 2023
Source
HAL
Keywords
Language
English
License
Unknown
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Abstract

Food and medicine are essential for maintaining a healthy life of organisms, in particular, humans. It is well-known that most of them contain chiral molecules, which are stereoisomers that are non-superimposable with each other. Due to this specific characteristic, the two forms of chiral molecules can either be biologically active or even toxic. In a typical process to synthesize chiral compounds, a racemate of the two chiral molecules are produced. To allow the production of enantiopure pharmaceutical compounds (EPC), chiral catalysts have to be developed to perform enantioselective synthesis or recognition of these compounds or to understand the functions of each chiral molecule. Chiral homogeneous catalysts are classically used for enantioselective synthesis but suffer from a difficult separation once the reaction is completed. Thus, chiral heterogeneous catalysts were proposed as an alternative, including chiral imprinted mesoporous metal (CIMM) electrodes. These CIMMs have been successfully elaborated by electroreduction of metal salts in the simultaneous presence of non-ionic surfactants to create mesoporous structures, and chiral molecules, to encode chiral information, respectively. The designer materials exhibit excellent efficiencies in both, enantioselective synthesis and recognition of various chiral molecules such as phenyl ethanol, mandelic acid, and 3,4-dihydroxy phenylalanine. Several metal compositions, such as Pt, Ni, and PtIr, were tested along with these chiral molecules.This thesis proposes several strategies to circumvent some limitations that are yet to be solved for CIMMs, for example, the use of cheap metals to design chiral encoded matrices, the synthesis of real pharmaceutical molecules, and the selective recognition of various types of chiral amino acids. Transition metals such as Cu and CuNi have been employed for the design of CIMMs with enantioselective features in a first part of the work.The second aspect is focused on imprinting a pharmaceutical molecule, epinephrine (EP), into PtIr CIMMs supported on Ni foam as heterogeneous catalysts, and an %ee of over 95% could be obtained.Finally, the concept of CIMMs was applied to the imprinting of chiral amino acids such as tyrosine and tryptophan. It could be shown that chiral metals imprinted with one amino acid enantiomer allow recognition of other amino acids with the same chiral configuration. Overall, these studies open up promising perspectives for the development of CIMMs as potential candidates for industrial pharmaceutical synthesis and as chiral sensors.

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