Model for hyaluronic acid incorporating four intramolecular hydrogen bonds

Atkins, E. D. T.; Meader, D.; Scott, J. E.

doi:10.1016/0141-8130(80)90053-7

Cited by 58 publications

(38 citation statements)

References 12 publications

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“…6,7,20 This model, while consistent with some experimental data, is at odds with the majority of the X-ray diffraction data, 3 hydrodynamic data for HA, 21 NMR observations 9,11 and results from molecular dynamics simulations in aqueous solution. 15 Crucially, but often over-looked, the diffraction pattern proposed to be a 2-fold helical structure has only been observed at non-physiological pH and the unit cell and chain packing have never been elucidated.…”

Section: Introductionsupporting

confidence: 52%

“…However, the presence and precise nature of intramolecular hydrogen bonds has been difficult to characterize in aqueous solution. [6][7][8][9] Studies using NMR have been largely unsuccessful in unequivocally characterizing the solution conformation 9,10 because the overlap present in NMR spectra severely limits the amount of resolved and specific information that can be obtained. More typically, measurements are averaged over the whole chain length, which are consequently vastly more problematic to interpret.…”

Section: Introductionmentioning

confidence: 99%

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Hyaluronan: The Local Solution Conformation Determined by NMR and Computer Modeling is Close to a Contracted Left-handed 4-Fold Helix

Almond

DeAngelis

Blundell

2006

Journal of Molecular Biology

108

113

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Section: Introductionsupporting

confidence: 52%

Section: Introductionmentioning

confidence: 99%

Hyaluronan: The Local Solution Conformation Determined by NMR and Computer Modeling is Close to a Contracted Left-handed 4-Fold Helix

Almond

DeAngelis

Blundell

2006

Journal of Molecular Biology

108

113

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“…The secondary structure Scott and his associates found early on [35,36] that was also summarized by Scott in a later review [37], involved intra-residue hydrogen bonds. Thus, it was a logical conclusion to ascribe the stiffness of hyaluronan to the presence of these hydrogen bonds.…”

Section: Secondary Structurementioning

confidence: 96%

Molecular structure of hyaluronan: an introduction

Hargittai

2008

Struct Chem

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Hyaluronan is an unbranched polysaccharide of repeating disaccharides consisting of D-glucuronic acid and N-acetyl-D-glucosamine. Its strong water-retaining ability and visco-elastic properties have been broadly utilized in medical applications. Hyaluronan is an important constituent of the extracellular matrix whose physiological functions are manifested both as the substance is by itself as well as when it is being linked to various proteins. Compared with other biopolymers, such as nucleic acids and proteins, the structural chemistry of hyaluronan is much less developed. The scarce information about the metrical aspects of its structure shows no unusual features. Its secondary structure is characterized by intramolecular hydrogen bonding that is hard to distinguish from hydrogen bonding involving water molecules when hyaluronan is in aqueous medium. The tertiary structure of hyaluronan is sensitively dependent on its environment. The relative rigidity of the glycosidic bond and the intramolecular hydrogen bonds would tend to restrict rotational freedom and thus conformational variability. This, however, seems to be overwritten by the impact of molecular environment leading to a great variability of tertiary structure. A large number of conformations are possible and may be present as witnessed by their rather small free energy differences.Of the plethora of physical techniques and computational methods, X-ray crystallography and molecular dynamics calculations have proved to be the most fruitful so far. There are untapped possibilities in NMR spectroscopy for structural studies and quantum chemical calculations are also expected to contribute substantially to the structural chemistry of hyaluronan. There are many basic data as well as structural intricacies of hyaluronan that have so far eluded the researchers of its molecular structure.

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“…Based on the anomalously slow rate of periodate oxidation kinetics for HA, Scott suggested that hydrogen bonds may be present in solution [11]. Further work, including nuclear magnetic resonance (NMR) in dimethyl sulphoxide, led to a conclusion that HA is a twofold helix in solution [12], which was hypothesised to be the basis of tertiary organisation in solution [13]. However, it should be noted that such a structure was only seen in x-ray diffraction patterns at non-physiological pH, and the organisation of the chains in those fibres has never been fully elucidated.…”

Section: Structural and Physical Studiesmentioning

confidence: 97%

Hyaluronan

Almond

2007

Cell. Mol. Life Sci.

181

139

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The polysaccharide hyaluronan is an essential component of the vertebrate extracellular matrix and also produced by viruses, bacteria and fungi. Although the hyaluronan polymer is simply a disaccharide that repeats many thousands of times, it has an amazing array of biological functions and medical uses. For example, it is an efficient space filler that maintains hydration, serves as a substrate for assembly of proteoglycans and cellular locomotion, regulates cellular function and development, and is involved in tumor progression, inflammation and wound healing. Its physical properties and biocompatibility also make it of considerable importance in the development of engineered tissue, biomaterials and in clinical applications.

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Model for hyaluronic acid incorporating four intramolecular hydrogen bonds

Cited by 58 publications

References 12 publications

Hyaluronan: The Local Solution Conformation Determined by NMR and Computer Modeling is Close to a Contracted Left-handed 4-Fold Helix

Hyaluronan: The Local Solution Conformation Determined by NMR and Computer Modeling is Close to a Contracted Left-handed 4-Fold Helix

Molecular structure of hyaluronan: an introduction

Hyaluronan

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