Mefloquine is an important drug for prevention and treatment of malaria. It is commercially available as a racemic mixture, wherein only one enantiomer is active against malaria, while the other one causes severe psychotropic effects. By converting the drug into a compound that crystallizes as a racemizable racemic conglomerate, the deracemization of mefloquine into the desired enantiomer was achieved.
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http://dx.doi.org/10.1002/anie.201811289 | DOI Listing |
Chemphyschem
September 2023
Laboratoire des IMRCP, UMR au CNRS No. 5623, Université Paul Sabatier 31062, Toulouse Cedex, France.
Attrition-enhanced chiral symmetry breaking in crystals, known as Viedma deracemization, is a promising method for converting racemic solid phases into enantiomerically pure ones under non-equilibrium conditions. However, many aspects of this process remain unclear. In this study, we present a new investigation into Viedma deracemization using a comprehensive kinetic rate equation continuous model based on classical primary nucleation theory, crystal growth, and Ostwald ripening.
View Article and Find Full Text PDFChirality
October 2022
Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, Texas, USA.
Org Process Res Dev
April 2022
Department of Chemical Engineering and Analytical Science, University of Manchester, M13 9PL Manchester, U.K.
Enantiomeric purity is of prime importance for several industries, specifically in the production of pharmaceuticals. Crystallization processes can be used to obtain pure enantiomers in a suitable solid form. However, some process variants inherently rely on kinetic enhancement (preferential crystallization) of the desired enantiomer or on complex interactions of several phenomena (e.
View Article and Find Full Text PDFChemistry
November 2021
Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.
Asymmetric synthesis was performed by combining the photochemical reaction of an achiral substrate followed by crystallization-induced deracemization. The results indicated that a fused indoline produced by photochemical intramolecular δ-hydrogen abstraction and cyclization of N-(5-chloro-2-methylphenyl)phthalimide crystallized as a racemic conglomerate. Since this substrate has an aminal skeleton, racemization involving a ring-opening and ring-closing equilibrium process occurred under suitable conditions.
View Article and Find Full Text PDFJ Am Chem Soc
February 2020
Department of Chemistry , Scripps Research Institute, La Jolla , California 92037 , United States.
The evolution of homochirality via attrition-enhanced deracemization (AED) of enantiomorphic solids is carried out using molecules that differ only in the isotopic composition of a phenyl group positioned remote from the chiral center. Enantioenrichment consistently favors the enantiomorph containing a deuterated phenyl group over the protio or C version, and the protio version is consistently favored over the C version. While these isotopic compounds exhibit identical crystal structures and solubilities, the trend in deracemization correlates with melting points.
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