The disaccharide repeating-units of heparan sulfate

Hovingh, Peter; Linker, Alfred

doi:10.1016/s0008-6215(00)87073-1

Cited by 74 publications

(22 citation statements)

References 28 publications

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“…These values may underestimate the proportion of N-sulphated disaccharide units in the intact polysaccharides, because of (a) the deaminative ring-contraction reaction that converts N-sulphated D-glucosamine residues to 2-aldehYdo-D-pentofuranoside units without cleavage of glycosidic linkages (Shively & Conrad, 1976a,b), and (b) the presence in the polysaccharides of-GIcNAc-uronic acid-GIcNSO3-sequences, in which the Al-acetylglucosaminidic linkage is resistant towards deaminative cleavage. Hovingh & Linker, 1974;Cifonelli & King, 1977). Interestingly, the same disaccharide units appear to prevail in so-called co-heparin from whale tissues (Kosakai et al, 1978).…”

Section: Identification Of Monosulphated Disaccharides; Sugar Moietiesmentioning

confidence: 91%

Identification of N-sulphated disaccharide units in heparin-like polysaccharides

Jacobsson¹,

Höök

Pettersson³

et al. 1979

Biochemical Journal

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1. Preparations of heparin and heparan sulphate were degraded with HNO2. The resulting disaccharides were isolated by gel chromatography, reduced with either NaBH4 or NaB3H4 and were then fractionated into non-sulphated, monosulphated and disulphated species by ion-exchange chromatography or by paper electrophoresis. The non-sulphated disaccharides were separated into two, and the monosulphated disaccharides into three, components by paper chromatography. 2. The uronic acid moieties of the various nonand mono-sulphated disaccharides were identified by means of radioactive labels selectively introduced into uronic acid residues (3H and 14C in D-glucuronic acid, 14C only in L-iduronic acid units) during biosynthesis of the polysaccharide starting material. Labelled uronic acids were also identified by paper chromatography, after liberation from disaccharides by acid hydrolysis or by glucuronidase digestion. Similar procedures, applied to disaccharides treated with NaB3H4, indicated 2,5-anhydro-D-mannitol as reducing terminal unit. On the basis of these results, and the known positions and configurations of the glycosidic linkages in heparin, the two non-sulphated disaccharides were identified as 4-0-(fi-D-glucopyranosyluronic acid)-2,5-anhydro-D-mannitol and 4-0-(a-L-idopyranosyluronic acid)-2,5-anhydro-D-mannitol. 3. The three monosulphated [1-3H]anhydromannitol-labelled disaccharides were subjected to Smith degradation or to digestion with homogenates of human skin fibroblasts, and the products were analysed by paper electrophoresis. The results, along with the 1H n.m.r. spectra ofthe corresponding unlabelled disaccharides, permitted the allocation of 0-sulphate groups to various positions in the disaccharides. These were thus identified as 4-0-(fl-D-glucopyranosyluronic acid)-2,5-anhydro-D-mannitol 6-sulphate, 4-0-(a-L-idopyranosyluronic acid)-2,5-anhydro-D-mannitol 6-sulphate and 4-0-(a-L-idopyranosyluronic acid 2-sulphate)-2,5-anhydro-D-mannitol. The last-mentioned disaccharide was found to be a poor substrate for the iduronate sulphatase of human skin fibroblasts, as compared with the disulphated species, 4-0-(a-L-idopyranosyluronic acid 2-sulphate)-2,5-anhydro-Dmannitol 6-sulphate. 4. The identified [1 -3H]anhydromannitol-labelled disaccharides were used as reference standards in a study of the disaccharide composition of heparins and heparan sulphates. Low N-sulphate contents, most pronounced in the heparan sulphates, were associated with high ratios of mono-O-sulphated/di-O-sulphated (N-sulphated) disaccharide units, and in addition, with relatively large amounts of 2-sulphated L-iduronic acid residues bound to C-4 of N-sulpho-D-glucosamine units lacking 0-sulphate substituents.

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Section: Identification Of Monosulphated Disaccharides; Sugar Moietiesmentioning

confidence: 91%

Identification of N-sulphated disaccharide units in heparin-like polysaccharides

Jacobsson¹,

Höök

Pettersson³

et al. 1979

Biochemical Journal

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“…Nitrous acid treatment of PG was carried out as described by Shively and Conrad (21). Heparitinase digestion was carried out as described by Hovingh and Linker (22). All digests were chromatographed on Sepharose CL-4B in 0.5 M sodium acetate, pH 5.8.…”

Section: Enzyme-linked Immunosorbent Assay (Elisa) Elisa Was Performmentioning

confidence: 99%

Sera from patients with poststreptococcal glomerulonephritis contain antibodies to glomerular heparan sulfate proteoglycan.

Fillit¹,

Damle²,

Gregory³

et al. 1985

The Journal of Experimental Medicine

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Proteoglycans (PG) ~ are important tissue components,both in the extracellular matrix (1) and as cell membrane-associated components (2). They are composed of protein and glycosaminoglycans (GAG), containing glucosamine or galactosamine and (generally) uronic acid. About fifty years ago, Goebel (3) demonstrated the antigenicity of protein-bound uronic acid and, further, showed that rabbit antisera could distinguish protein-bound glucuronic from galacturonic acid (4). More recently, the presence of immunity to heparan sulfate and chondroitin sulfate PG has been demonstrated in animals (5-7). Both protein core and GAG determinants are antigenic. Studies of systemic lupus erythematosus (SLE) sera (8) suggest that antibodies to DNA may cross-react with hyaluronate and chondroitin sulfate on a nonspecific charge basis because of the repeating anionic sites that DNA and GAG have in common.Previous studies (9-13) suggest that autoimmunity to a number of kidney antigens may exist in acute and chronic giomerulonephritis (GN). Our own work (13,14) suggests that the carbohydrate antigens of the giomerular basement membrane (GBM) may be antigenic. Since one of the major carbohydratecontaining antigens of the GBM is heparan sulfate PG (1), we studied the sera of patients with acute poststreptococcal glomerulonephritis (PSGN) for the presence of antibodies to glomerular PG. These studies demonstrate the presence, in PSGN sera, of antibodies to glomerular PG. Heparan sulfate is the primary target of immune reactivity. Mammalian hyaluronate and streptococcal hyaluronate inhibited the observed reactivity, suggesting cross-reactivity in the immune response to heparan sulfate, mammalian, and streptococcal hyaluronate. A second site of immunoreactivity contains N-acetylgalactosamine, possibly representing autoimmunity to chondroitin or dermatan sulfate PG.

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“…It has been well established that heparinase (4,5,13,32) exhibits an absolute substrate specificity for heparin in histochemical and biochemical systems, whereas chondroitinase ABC (30, 31) shows a relative substrate specificity for chondroitin sulfate A, B, C, D and E, chondroitin and hyaluronic acid in the same systems.…”

Section: Discussionmentioning

confidence: 99%

Electron microscopic cytochemical studies on sulfated glycosaminoglycans in rat mast cell granules.

Kida

1993

Acta Histochem. Cytochem

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Electron microscopic cytochemical studies have been made on sulfated glycosaminoglycans in mast cell granules from the rat peritoneal cavity by means of combined alcian blue (AB) pH 1.0-phosphotungstic acid (PTA) staining and enzyme (heparinase or chondroitinase ABC) digestion or chemical modification (nitrous acid) procedures. The results obtained revealed that the mast cell populations from the rat peritoneal cavity are grouped into at least three cell types on the basis of the molecular species of sulfated glycosaminoglycans contained in the cytoplasmic granules, the first cell type occupying the majority of the cell population with cytoplasmic granules containing primarily heparin, the second cell type being of an exceedingly small proportion with cytoplasmic granules containing primarily isomeric chondroitin sulfate (D and/or E), and the third cell type (intermediates between the first and second types) constituting a relatively small proportion with cytoplasmic granules containing two kinds of cytoplasmic granules containing heparin and isomeric chondroitin sulfate (D and/or E) respectively. In addition, unique substructures of cytoplasmic granules containing different sulfated glycosaminoglycans were disclosed such as tubular or thin thread-like elements, interstitial vesicles and surface spine-like figures.The present results are taken to represent the first electron microscopic cytochemical evidence that mast cell populations are heterogeneous in terms of molecular species of sulfated glycosaminoglycans contained in the cytoplasmic granules in mammals.

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The disaccharide repeating-units of heparan sulfate

Cited by 74 publications

References 28 publications

Identification of N-sulphated disaccharide units in heparin-like polysaccharides

Identification of N-sulphated disaccharide units in heparin-like polysaccharides

Sera from patients with poststreptococcal glomerulonephritis contain antibodies to glomerular heparan sulfate proteoglycan.

Electron microscopic cytochemical studies on sulfated glycosaminoglycans in rat mast cell granules.

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