19F NMR chemical shift prediction with fluorine fingerprint descriptor

Vulpetti, Anna; Landrum, Gregory A.; Rüdisser, Simon; Erbel, P.; Dalvit, Claudio

doi:10.1016/j.jfluchem.2009.12.024

Cited by 22 publications

(24 citation statements)

References 31 publications

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“…Firstly, the 19 F chemical shifts were predicted with the recently reported algorithm based on a fluorine fingerprint descriptor. [17] This method relies on a representative set of known chemical shifts measured for different fluorine local chemical environments (the LEF library). When the exact or similar fluorine fingerprint descriptor of the ligand is contained in the training set, its chemical shift can be predicted quite accurately.…”

Section: Methodsmentioning

confidence: 99%

Fluorine–Protein Interactions and ¹⁹F NMR Isotropic Chemical Shifts: An Empirical Correlation with Implications for Drug Design

2010

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An empirical correlation between the fluorine isotropic chemical shifts, measured by ¹⁹F NMR spectroscopy, and the type of fluorine-protein interactions observed in crystal structures is presented. The CF, CF₂, and CF₃ groups present in fluorinated ligands found in the Protein Data Bank were classified according to their ¹⁹F NMR chemical shifts and their close intermolecular contacts with the protein atoms. Shielded fluorine atoms, i.e., those with increased electron density, are observed primarily in close contact to hydrogen bond donors within the protein structure, suggesting the possibility of intermolecular hydrogen bond formation. Deshielded fluorines are predominantly found in close contact with hydrophobic side chains and with the carbon of carbonyl groups of the protein backbone. Correlation between the ¹⁹F NMR chemical shift and hydrogen bond distance, both derived experimentally and computed through quantum chemical methods, is also presented. The proposed "rule of shielding" provides some insight into and guidelines for the judicious selection of appropriate fluorinated moieties to be inserted into a molecule for making the most favorable interactions with the receptor.

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Section: Methodsmentioning

confidence: 99%

Fluorine–Protein Interactions and ¹⁹F NMR Isotropic Chemical Shifts: An Empirical Correlation with Implications for Drug Design

2010

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“…In order to overcome these difficulties, a combined strategy entirely based on NMR spectroscopy is proposed for rapid deconvolution of complex mixtures of fluorinated molecules, without the use of additional separation procedures. The first approach uses the 19 F chemical shift prediction based on the fingerprint descriptor, as previously reported . This method is useful for those chemical mixtures containing fluorine atoms that have different fingerprints.…”

Section: Resultsmentioning

confidence: 99%

“…The first approach uses the 19 F chemical shift prediction based on the fingerprint descriptor, as previously reported. [21] This method is useful for those chemical mixtures containing fluorine atoms that have different fingerprints. It relies on a representative set of known chemical shifts measured for different fluorine local chemical environments.…”

Section: Resultsmentioning

confidence: 99%

Technical and practical aspects of ¹⁹F NMR‐based screening: toward sensitive high‐throughput screening with rapid deconvolution

Dalvit

Vulpetti

2012

Magnetic Reson in Chemistry

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The technical and practical aspects of (19) F NMR-based screening against a macromolecular target are analyzed in detail. A novel method utilizing the relaxation of (19) F homonuclear double quantum coherence is proposed for performing NMR-based binding assays in a direct- or competition-mode format. A combined strategy based on (19) F NMR chemical shift prediction, 2D (19) F NMR DOSY, and 2D (19) F-(1) H NMR long-range COSY experiments is presented for the deconvolution of complex mixtures of fluorinated molecules generated by either addition of single compounds or by chemical synthesis. The approaches presented here allow the screening of complex mixtures, even in the case where the exact composition is not known, and the rapid identification of the binders contained in the mixtures.

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“…Such a difference in chemical shift arises from the different chemical groups attached to the F atoms in the compounds (Fig. 1) because the chemical shifts of F atoms are sensitive to the chemical environment (23). In the presence of eParE, chemical shift changes were observed for 2 (Fig.…”

Section: Relaxation Analysis and H-d Exchange Experiments For Epare Anmentioning

confidence: 98%

Escherichia coli Topoisomerase IV E Subunit and an Inhibitor Binding Mode Revealed by NMR Spectroscopy

Wong

et al. 2016

Journal of Biological Chemistry

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19F NMR chemical shift prediction with fluorine fingerprint descriptor

Cited by 22 publications

References 31 publications

Fluorine–Protein Interactions and ¹⁹F NMR Isotropic Chemical Shifts: An Empirical Correlation with Implications for Drug Design

Fluorine–Protein Interactions and ¹⁹F NMR Isotropic Chemical Shifts: An Empirical Correlation with Implications for Drug Design

Technical and practical aspects of ¹⁹F NMR‐based screening: toward sensitive high‐throughput screening with rapid deconvolution

Escherichia coli Topoisomerase IV E Subunit and an Inhibitor Binding Mode Revealed by NMR Spectroscopy

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19F NMR chemical shift prediction with fluorine fingerprint descriptor

Cited by 22 publications

References 31 publications

Fluorine–Protein Interactions and 19F NMR Isotropic Chemical Shifts: An Empirical Correlation with Implications for Drug Design

Fluorine–Protein Interactions and 19F NMR Isotropic Chemical Shifts: An Empirical Correlation with Implications for Drug Design

Technical and practical aspects of 19F NMR‐based screening: toward sensitive high‐throughput screening with rapid deconvolution

Escherichia coli Topoisomerase IV E Subunit and an Inhibitor Binding Mode Revealed by NMR Spectroscopy

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Fluorine–Protein Interactions and ¹⁹F NMR Isotropic Chemical Shifts: An Empirical Correlation with Implications for Drug Design

Fluorine–Protein Interactions and ¹⁹F NMR Isotropic Chemical Shifts: An Empirical Correlation with Implications for Drug Design

Technical and practical aspects of ¹⁹F NMR‐based screening: toward sensitive high‐throughput screening with rapid deconvolution