Hyaluronan: the absence of amide-carboxylate hydrogen bonds and the chain conformation in aqueous solution are incompatible with stable secondary and tertiary structure models

The Biochemical Journal
Charles D BlundellA Almond

Abstract

Contradictory descriptions for the aqueous solution conformation of the glycosaminoglycan hyaluronan (HA) exist in the literature. According to hydrodynamic and simulation data, HA molecules are stiffened by a rapidly interchanging network of transient hydrogen bonds at the local level and do not significantly associate at the global level. In marked contrast, models derived from NMR data suggest that the secondary structure involves persistent hydrogen bonds and that strong associations between chains can occur to form vast stable tertiary structures. These models require an extended 2-fold helical conformation of the HA chain and specific hydrogen bonds between amide and carboxylate groups. To test these descriptions, we have used 15N-labelled oligosaccharides and high-field NMR to measure pertinent properties of the acetamido group. The amide proton chemical shift perturbation and carboxylate group pK(a) value are inconsistent with a highly populated hydrogen bond between the amide and carboxylate groups. Amide proton temperature coefficients and chemical exchange rates confirm this conclusion. Comparison of oligomer properties with polymeric HA indicates that there is no discernible difference in amide proton environment be...Continue Reading

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Citations

Jul 5, 2007·Organic & Biomolecular Chemistry·Mehdi Mobli, Andrew Almond
Aug 3, 2011·Glycobiology·Benedict M Sattelle, Andrew Almond
Apr 20, 2011·Contrast Media & Molecular Imaging·Wenlian Zhu, Dmitri Artemov
Mar 22, 2014·Frontiers in Immunology·Aaron C Petrey, Carol A de la Motte
Mar 21, 2007·Magnetic Resonance in Chemistry : MRC·Charles D Blundell, Andrew Almond
Dec 18, 2013·Biomedical Materials·Eric AguadoDaniel Chappard
May 9, 2019·Chembiochem : a European Journal of Chemical Biology·Jerk RönnolsGöran Widmalm
Apr 10, 2020·Physical Chemistry Chemical Physics : PCCP·Eliane P van DamHuib J Bakker
Jan 8, 2013·Organic & Biomolecular Chemistry·Vassiliki G KontogianniIoannis P Gerothanassis
Feb 20, 2007·The Journal of Biological Chemistry·Charles D BlundellAnthony J Day
Jul 21, 2013·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Léa MessagerValérie Ravaine
Apr 11, 2009·Biomacromolecules·Paolo MatteiniRoberto Pini
Jun 24, 2021·International Journal of Biological Macromolecules·Biswajoy GhoshJyotirmoy Chatterjee
Aug 5, 2010·Journal of the American Chemical Society·Nicola R YaffeEwan W Blanch
Mar 20, 2019·The Journal of Physical Chemistry. B·Giulia GiubertoniHuib J Bakker
May 9, 2019·The Journal of Physical Chemistry. B·Andrew R GreenCynthia K Larive
Dec 29, 2020·Langmuir : the ACS Journal of Surfaces and Colloids·Lin WangQiang Wang
Aug 25, 2021·International Journal of Biological Macromolecules·Eva KutálkováVladimír Velebný
Mar 13, 2020·Environmental Science & Technology·Benjamin P FrankD Howard Fairbrother
Sep 4, 2019·The Journal of Physical Chemistry. a·Giulia GiubertoniHuib J Bakker

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