Specific Cleavage of Polysaccharides Containing Uronic Acid Residues by the Hoffman–Veerman Reaction

SummaryCommercial porcine heparin can be separated into three distinct subtractions by using DEAE-cellulose chromatography and a stepped salt gradient. Gram quantities of heparin can be fractionated by this technique. All three heparin subtractions can accelerate the inhibition of thrombin by antithrombin III with different efficiency. The specific activities of the high activity heparin, intermediate activity heparin and low activity heparin are 228 units/mg, 142 units/mg and 95 units/mg, respectively. Both the uronic acid content and the quantity of N-SO4 for all three heparin subfractions have been evaluated. The high activity heparin has the lowest uronic acid and N-SO4 content. The successful separation of commercial heparin into three distinct subfractions by means of ion-exchange chromatography suggests that the net charge on these three heparin components will serve as a model system in the elucidation of the structure and activity relationship to the biological function of heparin.

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Extracellular polysaccharides from suspension cultures of Nicotiana plumbaginifolia

10.26686/wgtn.12597827.v1 ◽

2020 ◽

Author(s):

Ian Sims ◽

A Bacic

Keyword(s):

Uronic Acid ◽

Cell Suspension Cultures ◽

Anion Exchange Chromatography ◽

Nicotiana Plumbaginifolia ◽

Suspension Cultures ◽

Exchange Chromatography ◽

Arabinogalactan Protein ◽

Extracellular Polysaccharides ◽

Selective Precipitation ◽

The Individual

The soluble polymers secreted by cell-suspension cultures of Nicotiana plumbaginifolia contained 78% carbohydrate, 6% protein and 4% inorganic material. The extracellular polysaccharides were separated into three fractions by anion-exchange chromatography using a gradient of imidazole-HCl at pH 7 and the individual polysaccharides in each fraction were then isolated by selective precipitation and enzymic treatment. Monosaccharide and linkage compositions were determined for each polysaccharide after reduction of uronic acid residues and the degree of esterification of the various uronic acid residues in each polysaccharide was determined concurrently with the linkage types. Six components were identified: an arabinoxyloglucan (comprising 34% of the total polysaccharide) and a galactoglucomannan (15%) in the unbound neutral fraction, a type II arabinogalactan (an arabinogalactan-protein, 11%) and an acidic xylan (3%) in the first bound fraction, and an arabinoglucuronomannan (11%) and a galacturonan (26%) in the second bound fraction. © 1995.

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Structure of a shear-thickening polysaccharide extracted from the New Zealand black tree fern, Cyathea medullaris

10.26686/wgtn.12597809.v1 ◽

2020 ◽

Author(s):

M Wee ◽

M Mastrangelo ◽

Susan Carnachan ◽

Ian Sims ◽

K Goh

Keyword(s):

New Zealand ◽

Uronic Acid ◽

Average Molecular Weight ◽

Shear Thickening ◽

Water Soluble ◽

Size Exclusion ◽

Resonance Spectroscopy ◽

Tree Fern ◽

13C Nuclear Magnetic Resonance ◽

Exclusion Chromatography

A shear-thickening water-soluble polysaccharide was purified from mucilage extracted from the fronds of the New Zealand black tree fern (Cyathea medullaris or 'mamaku' in Māori) and its structure characterised. Constituent sugar analysis by three complementary methods, combined with linkage analysis (of carboxyl reduced samples) and 1H and 13C nuclear magnetic resonance spectroscopy (NMR) revealed a glucuronomannan comprising a backbone of 4-linked methylesterified glucopyranosyl uronic acid and 2-linked mannopyranosyl residues, branched at O-3 of 45% and at both O-3 and O-4 of 53% of the mannopyranosyl residues with side chains likely comprising terminal xylopyranosyl, terminal galactopyranosyl, non-methylesterified terminal glucopyranosyl uronic acid and 3-linked glucopyranosyl uronic acid residues. The weight-average molecular weight of the purified polysaccharide was ~1.9×106Da as determined by size-exclusion chromatography coupled with multi-angle laser light scattering (SEC-MALLS). The distinctive rheological properties of this polysaccharide are discussed in relation to its structure. © 2014 Elsevier B.V.

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Binding of lead and copper(II) cations to hemicelluloses of rye bran

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19862250 ◽

1986 ◽

Vol 51 (10) ◽

pp. 2250-2258 ◽

Cited By ~ 10

Author(s):

Rudolf Kohn ◽

Zdena Hromádková ◽

Anna Ebringerová

Keyword(s):

Uronic Acid ◽

Equilibrium Solution ◽

Glucuronic Acid ◽

The Other ◽

Carboxyl Groups ◽

Stoichiometric Ratio ◽

Molar Ratios ◽

Free Ions ◽

Uronic Acid Content ◽

The Relationship

Several fractions of acid hemicelluloses isolated from rye bran were characterized by molar ratios of saccharides (D-Xyl, L-Ara, D-Glc, D-Gal) and 4-O-methyl-D-glucuronic acid and protein content. Binding of Pb2+ and Cu2+ ions to these acid polysaccharides was considered according to function (M)b = f([M2+]f), expressing the relationship between the amount of metal (M)b bound to 1 g of the substance and the concentration of free ions [M2+]f in the equilibrium solution and according to the association degree β of these cations with carboxyl groups of uronic acid at a stoichiometric ratio of both components in the system under investigation. Acid hemicelluloses contained only a very small portion of uronic acid ((COOH) 0.05-0.18 mmol g-1); the model polysaccharide, 4-O-methyl-D-glucurono-D-xylan of beech, was substantially richer in uronic acid content ((COOH) 0.73 mmol g-1). Consequently, the amount of lead and copper bound to acid hemicelluloses is very small ((M)b 0.017-0.025 mmol g-1) at [M2+]f = 0.10 mmol l-1. On the other hand, much greater amount of cations ((M)f 0.09-0.10 mmol g-1) was bound to the glucuronoxylan. The association degree β was like with the majority of samples (β = 0.31-0.38). The amount of lead and copper(II) bound to acid hemicelluloses from rye bran is several times lower than that bound to dietary fiber isolated from vegetables (cabbage, carrot), rich in pectic substances.

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CORRESPONDENCE. Noninterference of Pectinous Substances in Aconitic Acid Method and of Aconitic Acid in Uronic Acid Method

Analytical Chemistry ◽

10.1021/ac60021a027 ◽

1948 ◽

Vol 20 (9) ◽

pp. 880-880 ◽

Cited By ~ 1

Author(s):

J A. Ambler ◽

E J. Roberts

Keyword(s):

Uronic Acid ◽

Acid Method ◽

Aconitic Acid

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The antiproliferative activity of arterial heparan sulfate resides in domains enriched with 2-O-sulfated uronic acid residues.

Journal of Biological Chemistry ◽

10.1016/s0021-9258(18)41767-x ◽

1992 ◽

Vol 267 (27) ◽

pp. 19242-19247

Author(s):

A Schmidt ◽

K Yoshida ◽

E Buddecke

Keyword(s):

Heparan Sulfate ◽

Antiproliferative Activity ◽

Uronic Acid

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Ancient origin of fucosylated xyloglucan in charophycean green algae

Communications Biology ◽

10.1038/s42003-021-02277-w ◽

2021 ◽

Vol 4 (1) ◽

Author(s):

Maria Dalgaard Mikkelsen ◽

Jesper Harholt ◽

Bjørge Westereng ◽

David Domozych ◽

Stephen C. Fry ◽

...

Keyword(s):

Green Algae ◽

Structural Component ◽

Cell Walls ◽

Uronic Acid ◽

Structural Elucidation ◽

Land Plants ◽

Evolutionary Significance ◽

Biosynthetic Enzymes ◽

Major Structural Component ◽

Mesotaenium Caldariorum

AbstractThe charophycean green algae (CGA or basal streptophytes) are of particular evolutionary significance because their ancestors gave rise to land plants. One outstanding feature of these algae is that their cell walls exhibit remarkable similarities to those of land plants. Xyloglucan (XyG) is a major structural component of the cell walls of most land plants and was originally thought to be absent in CGA. This study presents evidence that XyG evolved in the CGA. This is based on a) the identification of orthologs of the genetic machinery to produce XyG, b) the identification of XyG in a range of CGA and, c) the structural elucidation of XyG, including uronic acid-containing XyG, in selected CGA. Most notably, XyG fucosylation, a feature considered as a late evolutionary elaboration of the basic XyG structure and orthologs to the corresponding biosynthetic enzymes are shown to be present in Mesotaenium caldariorum.

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Binding of calcium, lead, and copper(II) cations to galactaric and 2,5-furandicarboxylic acids and to D-galacturonic acid and its derivatives

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19861150 ◽

1986 ◽

Vol 51 (5) ◽

pp. 1150-1159 ◽

Cited By ~ 8

Author(s):

Rudolf Kohn ◽

Ján Hirsch

Keyword(s):

Galacturonic Acid ◽

Uronic Acid ◽

Indicator Method ◽

Cu Complex ◽

Carboxylate Groups ◽

Counter Ions ◽

Galactaric Acid ◽

Furandicarboxylic Acid ◽

The Difference ◽

Calcium Lead

The binding of Ca2+, Pb2+, and Cu2+ ions to galactaric and 2,5-furandicarboxylic acids and of Pb2+ and Cu2+ ions to D-galacturonic acid, its α-methylglycoside, and (methyl-4-deoxy-α-D-galactopyranosid)uronic acid was evaluated in terms of the activity coefficients of the counter-ions and the degrees of their association with the carboxylate groups of the acids. The activity of Ca2+ ions was determined by the metallochromic indicator method with tetramethylmurexide, that of Pb2+ and Cu2+ ions, with ion specific electrodes. Galactaric acid bids 89.5% Ca2+ ions, practically all (99.9%) Pb2+ ions and nearly all (98.6% Cu2+ ions, mostly with the formation of insoluble salts. As little as 7.6% Ca2+, 34.0% Pb2+, and 23.9% Cu2+ were bound to 2,5-furandicarboxylic acid in the form of soluble complexes, and slightly more, 4.1% Ca2+, 43.9% Pb2+, and 38.0% Cu2+, to D-galacturonic acid. The difference in the degrees of binding to galactaric acid and 2,5-furandicarboxylic acid is due to the different flexibility of their molecular skeletons. The activities of Pb2+ and Cu2+ ions in solutions of salts of D-galacturonic acid and its derivatives indicate that the OH group at C(4) of D-galacturonic acid takes part in the complexation. For the Pb2+ complex, the OH group at C(1) of the unsubstituted acid in the β-anomeric form also seems to participate in the complexation; this is not the case with the similar Cu complex.

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