Hydroxyl-proton hydrogen bonding in the heparin oligosaccharide Arixtra in aqueous solution

The Journal of Physical Chemistry. B
Consuelo N BeecherCynthia K Larive

Abstract

Heparin is best known for its anticoagulant activity, which is mediated by the binding of a specific pentasaccharide sequence to the protease inhibitor antithrombin-III (AT-III). Although heparin oligosaccharides are thought to be flexible in aqueous solution, the recent discovery of a hydrogen bond between the sulfamate (NHSO3(-)) proton and the adjacent 3-O-sulfo group of the 3,6-O-sulfated N-sulfoglucosamine residue of the Arixtra (fondaparinux sodium) pentasaccharide demonstrates that definable elements of local structure are accessed. Molecular dynamics simulations of Arixtra suggest the presence of additional hydrogen bonds involving the C3-OH groups of the glucuronic acid and 2-O-sulfo-iduronic acid residues. NMR measurements of temperature coefficients, chemical shift differences, and solvent exchange rate constants provide experimental confirmation of these hydrogen bonds. We note that the extraction of rate constants from cross-peak buildup curves in 2D exchange spectroscopy is complicated by the presence of radiation damping in aqueous solution. A straightforward model is presented that explicitly takes into account the effects of radiation damping on the water proton relaxation and is sufficiently robust to provide ...Continue Reading

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Citations

May 13, 2014·Progress in Nuclear Magnetic Resonance Spectroscopy·Marcos D BattistelDarón I Freedberg
Jan 14, 2016·Analytical and Bioanalytical Chemistry·Consuelo N BeecherCynthia K Larive
Apr 18, 2014·Environmental and Molecular Mutagenesis·Dennie G A J HebelsJos C S Kleinjans
Sep 5, 2015·The Journal of Physical Chemistry. B·Miloš Hricovíni
Jun 7, 2016·International Journal of Cardiology·Edwin A Yates, Timothy R Rudd
Dec 21, 2016·The Journal of Physical Chemistry. B·Marcos D BattistelDarón I Freedberg
Mar 4, 2017·The Journal of Physical Chemistry. a·Hai XuMartin Saunders
Nov 14, 2018·Chemistry : a European Journal·Kirill Nikitin, Ryan O'Gara
Feb 13, 2019·Magnetic Resonance in Chemistry : MRC·Marc B TarabanYihua Bruce Yu
Sep 4, 2014·Chemical Communications : Chem Comm·David G BelairWilliam L Murphy
May 9, 2019·Chembiochem : a European Journal of Chemical Biology·Jerk RönnolsGöran Widmalm
Nov 25, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Miloš Hricovíni, Michal Hricovíni
May 14, 2019·Wiley Interdisciplinary Reviews. Computational Molecular Science·Balaji NagarajanUmesh R Desai
May 9, 2019·The Journal of Physical Chemistry. B·Andrew R GreenCynthia K Larive

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