Measurement of long-range 1H-19F scalar coupling constants and their glycosidic torsion dependence in 5-fluoropyrimidine-substituted RNA.

Journal of the American Chemical Society
Mirko HennigJames R Williamson

Abstract

Long-range scalar 5J(H1',F) couplings were observed in 5-fluoropyrimidine-substituted RNA. We developed a novel S3E-19F-alpha,beta-edited NOESY experiment for quantitation of these long-range scalar 5J(H1',F) couplings, where the J-couplings can be extracted from inspection of intraresidual (H1',H6) NOE cross-peaks. Quantum chemical calculations were exploited to investigate the relation between scalar couplings and conformations around the glycosidic bond in oligonucleotides. The theoretical dependence of the observed 5J(H1',F) couplings on the torsion angle chi can be described by a generalized Karplus relationship. The corresponding density functional theory (DFT) analysis is outlined. Additional NMR experiments facilitating the resonance assignments of 5-fluoropyrimidine-substituted RNAs are described, and chemical shift changes due to altered shielding in the presence of fluorine-19 (19F) are presented.

References

Sep 11, 1992·Nucleic Acids Research·E P NikonowiczA Pardi
Jan 31, 1968·Journal of the American Chemical Society·R J CushleyJ J Fox
Nov 1, 1995·Journal of Biomolecular NMR·F DelaglioA Bax
Jan 1, 1995·Methods in Enzymology·M A Keniry, R H Shafer
Nov 1, 1996·Journal of Magnetic Resonance. Series B·T Maurer, H R Kalbitzer
Feb 1, 1997·Journal of Biochemical and Biophysical Methods·J J BarchiV E Marquez
May 8, 1998·Journal of Magnetic Resonance·M OttigerA Bax
Sep 15, 1988·Physical Review A: General Physics·A D Becke
Jan 5, 2000·Journal of Magnetic Resonance·J R Arnold, J Fisher
Mar 21, 2002·Journal of Molecular Biology·Kwaku T DayieJames R Williamson
Mar 20, 2003·Journal of the American Chemical Society·Markéta L Munzarová, Vladimír Sklenár
Jul 10, 2004·Journal of Biomolecular NMR·Radovan FialaVladimír Sklenár
Sep 9, 2004·Frontiers in Bioscience : a Journal and Virtual Library·Anila SeelamgariFatah Kashanchi
Sep 24, 2004·Journal of the American Chemical Society·Lincoln G ScottMirko Hennig
Apr 1, 1995·Journal of Biomolecular NMR·G LippensJ M Wieruszeski

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Citations

Jun 7, 2008·Organic Letters·Nivrutti B BarhateSnorri Th Sigurdsson
Mar 20, 2012·Journal of Magnetic Resonance·Denis Courtier-MuriasAndré J Simpson
Mar 15, 2018·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Thaís M BarbosaCláudio F Tormena
Jun 2, 2015·Chemical Communications : Chem Comm·Shigetaka Nakamura, Kenzo Fujimoto
Feb 4, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Nilamoni NathNagarajarao Suryaprakash
Jun 13, 2019·Current Medicinal Chemistry·Cong Bao Kang
Sep 8, 2016·Chemistry : a European Journal·Lotta Granqvist, Pasi Virta
Jul 15, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nadiia V PikunYuriy G Shermolovich
Jan 27, 2011·Physical Chemistry Chemical Physics : PCCP·Ali EbrahimiSophia Bazzi
Dec 13, 2017·Magnetic Resonance in Chemistry : MRC·Sandeep Kumar Mishra, N Suryaprakash
Jun 20, 2020·Angewandte Chemie·Felix NußbaumerChristoph Kreutz
Jul 12, 2020·Journal of Biomolecular NMR·Andras BoeszoermenyiGerhard Wagner
Apr 3, 2009·Inorganic Chemistry·Olena V ZenkinaMilko E van der Boom
Jun 5, 2010·Journal of the American Chemical Society·Anu Kiviniemi, Pasi Virta
Nov 10, 2007·Journal of the American Chemical Society·Mirko HennigJames R Williamson
Jun 8, 2021·Chemical Science·Maximilian HimmelstoßRonald Micura
Feb 19, 2020·Journal of the American Chemical Society·Qiang LiChuanzheng Zhou
Dec 18, 2019·Analytical Chemistry·Thaís M BarbosaClaudio F Tormena

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