Enzymatic and chemical methods for the generation of pure hyaluronan oligosaccharides with both odd and even numbers of monosaccharide units

Analytical Biochemistry
Charles D Blundell, Andrew Almond

Abstract

Hyaluronan oligosaccharides display physiological activities not associated with the polymer and are widely used to characterize hyaluronan-binding proteins. They can also be used as biocompatible starting blocks for chemical derivatization. Here we present methods for generating milligram quantities of unusual odd- and even-numbered oligosaccharides, greatly increasing the diversity of reagents for use in such studies. These methods are based upon protocols from the 1960s, at which time it was very difficult to assess the stereochemical purity of the products. To address this, products were analyzed with modern high-field nuclear magnetic resonance spectroscopy. Alkaline beta-elimination conditions previously used to remove reducing-terminal N-acetylglucosamine residues in fact introduce a significant ( approximately 30%) level of stereoisomerism in the products by alkali-catalyzed keto-enol tautomerizations. Milder alkaline conditions were used to overcome this problem, reducing the contamination to <5%. The elimination by-products from this reaction were isolated and characterized, allowing the mechanism of alkaline degradation of hyaluronan to be investigated for the first time. beta-Glucuronidase was used to remove nonredu...Continue Reading

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Citations

Mar 30, 2012·Biomacromolecules·Clark J NeedhamAntonios G Mikos
Dec 27, 2011·Applied Microbiology and Biotechnology·Anaïs A E ChavarocheGerrit Eggink
Aug 25, 2007·Biotechnology Advances·Robert SternLadislav Soltés
Mar 15, 2015·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Martin RothenhöferArmin Buschauer
Mar 21, 2007·Magnetic Resonance in Chemistry : MRC·Charles D Blundell, Andrew Almond
Feb 20, 2007·The Journal of Biological Chemistry·Charles D BlundellAnthony J Day
Sep 16, 2019·Carbohydrate Polymers·Jakub SedláčekVladimír Velebný
Oct 15, 2020·Carbohydrate Polymers·Matěj ŠimekVladimír Havlíček

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