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Rapid Measurement of Heteronuclear Coupling Constants in Complex NMR Spectra

[Image: see text] The NMR analysis of fluorine-containing molecules, increasingly widespread due to their importance in pharmaceuticals and biochemistry, poses significant challenges. Severe peak overlap in the proton spectrum often hinders the extraction of critical structural information in the fo...

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Detalles Bibliográficos
Autores principales: Mycroft, Coral, Dal Poggetto, Guilherme, Barbosa, Thaís M., Tormena, Cláudio F., Nilsson, Mathias, Morris, Gareth A., Castañar, Laura
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10510310/
https://www.ncbi.nlm.nih.gov/pubmed/37650656
http://dx.doi.org/10.1021/jacs.3c05515
Descripción
Sumario:[Image: see text] The NMR analysis of fluorine-containing molecules, increasingly widespread due to their importance in pharmaceuticals and biochemistry, poses significant challenges. Severe peak overlap in the proton spectrum often hinders the extraction of critical structural information in the form of heteronuclear scalar coupling constants, which are crucial for determining pharmaceutical properties and biological activity. Here, a new method, IPAP-FESTA, is reported that drastically simplifies measurements of the signs and magnitudes of proton–fluorine couplings. Its usefulness is demonstrated for the structural study of the steroidal drug fluticasone propionate extracted from a commercial formulation and for assessing solvent effects on the conformational equilibrium in a physically inseparable fluorohydrin mixture.