[NMR paper] Weak Intermolecular Hydrogen Bonds with Fluorine: Detection and Implications for Enzymatic/Chemical Reactions, Chemical Properties, and Ligand/Protein Fluorine NMR Screening.
Weak Intermolecular Hydrogen Bonds with Fluorine: Detection and Implications for Enzymatic/Chemical Reactions, Chemical Properties, and Ligand/Protein Fluorine NMR Screening.
Related ArticlesWeak Intermolecular Hydrogen Bonds with Fluorine: Detection and Implications for Enzymatic/Chemical Reactions, Chemical Properties, and Ligand/Protein Fluorine NMR Screening.
Chemistry. 2016 Apr 26;
Authors: Dalvit C, Vulpetti A
Abstract
It is known that strong hydrogen-bonding interactions play an important role in many chemical and biological systems. However, weak or very weak hydrogen bonds, which are often difficult to detect and characterize, may also be relevant in many recognition and reaction processes. Fluorine serving as a hydrogen-bond acceptor has been the subject of many controversial discussions and there are different opinions about it. It now appears that there is compelling experimental evidence for the involvement of fluorine in weak intramolecular or intermolecular hydrogen bonds. Using established NMR methods, we have previously characterized and measured the strengths of intermolecular hydrogen-bond complexes involving the fluorine moieties CH2 F, CHF2 , and CF3 , and have compared them with the well-known hydrogen-bond complex formed between acetophenone and the strong hydrogen-bond donor p-fluorophenol. We now report evidence for the formation of hydrogen bonds involving fluorine with significantly weaker donors, namely 5-fluoroindole and water. A simple NMR method is proposed for the simultaneous measurement of the strengths of hydrogen bonds between an acceptor and a donor or water. Important implications of these results for enzymatic/chemical reactions involving fluorine, for chemical and physical properties, and for ligand/protein (19) F NMR screening are analyzed through experiments and theoretical simulations.
PMID: 27112430 [PubMed - as supplied by publisher]
Affinity screening using competitive binding with fluorine-19 hyperpolarized ligands
From The DNP-NMR Blog:
Affinity screening using competitive binding with fluorine-19 hyperpolarized ligands
Kim, Y. and C. Hilty, Affinity screening using competitive binding with fluorine-19 hyperpolarized ligands. Angew Chem Int Ed Engl, 2015. 54(16): p. 4941-4.
http://www.ncbi.nlm.nih.gov/pubmed/25703090
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[NMR paper] Dual screening of BPTF and Brd4 using protein-observed fluorine NMR uncovers new bromodomain probe molecules.
Dual screening of BPTF and Brd4 using protein-observed fluorine NMR uncovers new bromodomain probe molecules.
Dual screening of BPTF and Brd4 using protein-observed fluorine NMR uncovers new bromodomain probe molecules.
ACS Chem Biol. 2015 Jul 9;
Authors: Urick AK, Hawk LM, Cassel MK, Mishra NK, Liu S, Adhikari N, Zhang W, Dos Santos CO, Hall JL, Pomerantz WC
Abstract
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[NMR paper] Exploring Weak Ligand-Protein Interactions by Long-Lived NMR States : Improved Contrast in Fragment-Based Drug Screening.
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Abstract
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[NMR paper] Fast-pulsing NMR techniques for the detection of weak interactions: successful natural abundance probe of hydrogen bonds in peptides.
Fast-pulsing NMR techniques for the detection of weak interactions: successful natural abundance probe of hydrogen bonds in peptides.
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Org Biomol Chem. 2013 Nov 21;11(43):7611-5
Authors: Altmayer-Henzien A, Declerck V, Aitken DJ, Lescop E, Merlet D, Farjon J
Abstract
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[NMR paper] (19)F NMR spectroscopy monitors ligand binding to recombinantly fluorine-labelled b'x from human protein disulphide isomerase (hPDI).
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Org Biomol Chem. 2014 May 6;
Authors: Curtis-Marof R, Doko D, Rowe ML, Richards KL, Williamson RA, Howard MJ
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[NMR paper] Fluorine NMR-Based Screening on Cell Membrane Extracts.
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ChemMedChem. 2013 Dec 11;
Authors: Veronesi M, Romeo E, Lambruschini C, Piomelli D, Bandiera T, Scarpelli R, Garau G, Dalvit C
Abstract
The possibility of measuring the action of inhibitors of specific enzymatic reactions in intact cells, cell lysates or membrane preparations represents a major advance in the lead discovery process. Despite the relevance of assaying in physiological conditions, only a small...
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Fluorine-Protein Interactions and (19)F NMR Isotropic Chemical Shifts: An Empirical Correlation with Implications for Drug Design.
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ChemMedChem. 2010 Nov 29;
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[NMR paper] Fluorine-NMR experiments for high-throughput screening: theoretical aspects, practica
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Competition ligand-based NMR screening experiments have recently been introduced to overcome most of the problems associated with traditional ligand-based NMR...
Weak Intermolecular Hydrogen Bonds with Fluorine: Detection and Implications for Enzymatic/Chemical Reactions, Chemical Properties, and Ligand/Protein Fluorine NMR Screening.
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