Exploring long-range fluorine-carbon J-coupling for conformational analysis of deoxyfluorinated disaccharides: A combined computational and NMR study
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
38678775
DOI
10.1016/j.bioorg.2024.107388
PII: S0045-2068(24)00293-1
Knihovny.cz E-resources
- Keywords
- Conformation, DFT calculations, Fluorine, NMR spectroscopy, Saccharides,
- MeSH
- Disaccharides * chemistry MeSH
- Fluorine * chemistry MeSH
- Carbohydrate Conformation MeSH
- Magnetic Resonance Spectroscopy * MeSH
- Molecular Conformation MeSH
- Density Functional Theory * MeSH
- Carbon chemistry MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
In this study, we investigated the potential of long-range fluorine-carbon J-coupling for determining the structures of deoxyfluorinated disaccharides. Three disaccharides, previously synthesized as potential galectin inhibitors, exhibited through-space fluorine-carbon J-couplings. In our independent conformational analysis of these disaccharide derivatives, we employed a combination of density functional theory (DFT) calculations and nuclear magnetic resonance (NMR) experiments. By comparing the calculated nuclear shieldings with the experimental carbon chemical shifts, we were able to identify the most probable conformers for each compound. A model comprising fluoromethane and methane molecules was used to study the relationship between molecular arrangements and intermolecular through-space J-coupling. Our study demonstrates the important effect of internuclear distance and molecular orientation on the magnitude of fluorine-carbon coupling. The experimental values for the fluorine-carbon through-space couplings (TSCs) of the disaccharides corresponded with values calculated for the most probable conformers identified by the conformational analysis. These results unlock the broader application of fluorine-carbon TSCs as powerful tools for conformational analysis of flexible molecules, offering valuable insights for future structural investigations.
References provided by Crossref.org
Influence of Selective Deoxyfluorination on the Molecular Structure of Type-2 N-Acetyllactosamine
