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At least 19 recordsLinked to original sources
PubMed1997

[Synthesis of terminal disaccharide of Forssman antigen and its analogs as spacer glycosides and free disaccharides].

Spacered terminal disaccharide of Forssman's antigen GalNAc alpha 1-3GalNAc beta 1-Osp, its analog GalNAc alpha 1-3GalNAc alpha 1-Osp, and disaccharides Gal beta 1-3GalNAc beta 1-Osp and Gal alpha 1-3GalNAc alpha 1-Osp [where sp denotes the (CH2)3NHCOCF3 spacer] were synthesized. Spacered disaccharides were obtained from the (3-trifluoroacetamidopropyl)-2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D- galactopyranoside and its alpha- and beta-analogs in which the 2-azido group was substituted for the 2-acetamido group. The azide glycosyl acceptors gave higher yields of the disaccharides. Azide glycosyl acceptors were prepared by the stereoselective glycosylation of 3-trifluoroacetamidopropanol with a mixture of 1-O-acetates of the 2-azido-3,4,6-tri-O-acetyl-2-deoxy-D-galactopyranose anomers in the presence of Lewis acids. Disaccharides Gal alpha 1-3GalNAc and GalNAc alpha 1-3GalNAc were obtained from the benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranoside.

Carbohydrate Sequence↗
PubMed2002

High-performance capillary electrophoretic analysis of hyaluronan and galactosaminoglycan-disaccharides in gastrointestinal carcinomas. Differential disaccharide composition as a possible tool-indicator for malignancies.

The glycosaminoglycans (GAGs) have documented implications for the growth and progression of malignant tumors. Gastrointestinal carcinomas (gastric, colon, rectum and pancreatic) are the most frequent malignancies occurring in human. GAGs, isolated from the tissues after digestion with papain, were analyzed by high-performance capillary electrophoresis (HPCE) following treatment with chondroitinase ABC. The composition of GAGs in disaccharides derived from the various gastrointestinal carcinomas was compared with those of normal tissues. We report that human gastrointestinal carcinomas are characterized by increased concentrations of GAGs, which have quite different disaccharide composition which, in turn, is associated with marked increase of non-sulfated (Delta(di)-nonS) and 6-sulfated (Delta(di)-mono6S) Delta-disaccharides. Particularly, a 12-51-fold increase in Delta(di)-nonS and a 3-42-fold increase in Delta(di)-mono6S content characterize these carcinomas, while the 4-sulfated units (Delta(di)-mono4S) showed a lower increase, about 0.5-1.5-fold. Moreover, the quantitation of hyaluronan (HA)-derived Delta-disaccharides (Delta(di)-nonS(HA)) also revealed a marked increase (1-12-fold) in the malignant tissues. On the other hand, the content of the chondroitinase ABC-resistant GAGs showed a low decrease, about 0.2-0.7-fold. The high amounts of hyaluronan (HA) produced by these carcinomas and the ectopic production of chondroitin sulphate (CS) proteoglycans, in which (Delta(di)-nonS) and (Delta(di)-mono6S) predominated, suggest a close relation between the content of these GAGs and the malignant phenotype, the metastatic ability and the survival time.

Disaccharides↗
PubMed2004

Search for serum protein-binding disaccharides and disaccharide-binding serum proteins by affinity capillary electrophoresis.

The potential use of affinity capillary electrophoresis in a microscale search for mutually interacting substances in biological fluid is demonstrated. Some disaccharides, especially gentiobiose (Gen), derivatized with 1-phenyl-3-methyl-5-pyrazolone, caused peak retardation when electrophoresed in a neutral running buffer, containing human serum. Gen, the most significantly retarded disaccharide, was converted to its negatively charged bis-mercaptoethanesulfonate derivative (MerESGen), and a serum sample was analyzed in a neutral buffer containing the derivatized disaccharide. Two peaks, belonging to the beta-globulin fraction, were found to be remarkably retarded in the buffer containing MerES-Gen in a concentration-dependent way. These findings prove an interaction between disaccharides and serum proteins.

Beta-Globulins↗
PubMed1978

Micro determination of unsaturated disaccharide formed by the action of acidic glycosaminoglycan-endoeliminases. An application of the thiobarbituric acid method to the assay of D-gluco-4-enepyranosyluronic acid-containing disaccharides.

An improved method is described for the micro determination of acidic glycosaminoglycans after digestion with chondroitinase-ABC and -AC. The determination is based on the color production of D-gluco-4-enepyranosyluronic acid-containing disaccharides produced by the action of chondroitinase-ABC and -AC (acidic glycosaminoglycans-endoeliminase) when the periodate-thiobarbituric acid method is applied to the alpha,beta-unsaturated disaccharides. Suitable conditions for the quantitative assay are described.

Chondroitin Sulfates↗
PubMed1984

Chemical synthesis and serology of disaccharides and trisaccharides of phenolic glycolipid antigens from the leprosy bacillus and preparation of a disaccharide protein conjugate for serodiagnosis of leprosy.

We examined the structural requirements within the species-specific 3,6-di-O-methyl-beta-D-glucopyranosyl-(1 leads to 4)-2,3-di-O-methyl- alpha-L-rhamnopyranosyl-(1 leads to 2)-3-O-methyl-alpha-L-rhamnopyranose unit of the phenolic glycolipid I antigen of Mycobacterium leprae for binding to anti-glycolipid immunoglobulin M from human leprosy sera. We used chemically defined, partially deglycosylated fragments of phenolic glycolipid I, two other minor M. leprae-specific phenolic glycolipids (those containing 6-O-methyl-beta-D-glucopyranosyl-(1 leads to 4)-2,3-di-O-methyl-alpha- L-rhamnopyranosyl-(1 leads to 2)-3-O-methyl-alpha-L-rhamnopyranose and 3,6-di-O-methyl-beta-D-glucopyranosyl-(1 leads to 4)-3-O-methyl-alpha- L-rhamnopyranosyl-(1 leads to 2)-3-O-methyl-alpha-rhamnopyranose units), and phenolic glycolipids from other mycobacteria. Additionally, the trisaccharide of phenolic glycolipid I, the 3,6-di-O-methyl-beta-D-glucopyranosyl-(1 leads to 4)-2, 3-di-O-methyl-alpha-L-rhamnopyranose, the 6-O-methyl-beta-D-glucopyranosyl-(1 leads to 4)-2,3-di-O-methyl-alpha- L-rhamnopyranose, and the beta-D-glucopyranosyl-(1 leads to 4)-2,3-di-O-methyl-alpha- L-rhamnopyranose disaccharides were synthesized and characterized, and their activities were examined. Only the phenolic glycolipids containing 3,6-di-O-methyl-beta-D-glucopyranosyl at the nonreducing terminus were efficient in binding the anti-glycolipid immunoglobulin M, and the 3,6-di-O-methyl-beta-D-glucopyranosyl-containing di- and trisaccharides were the most effective in inhibiting this binding. Thus, the 3,6-di-O-methyl-beta-D-glucopyranosyl substituent was recognized as the primary antigen determinant in phenolic glycolipid I. With this information, bovine serum albumin containing reductively aminated 3,6-di-O-methyl-beta-D-glucopyranosyl-(1 leads to 4)-2,3-di-O-methyl- L-rhamnose was prepared and shown to be highly active in the serodiagnosis of leprosy.

Antigens, Bacterial↗
PubMedDate not supplied

[Features of the effects of disaccharide structure of saccharose on kinetic parameters of hepatic lipid synthesis from glucose (mechanism of disaccharide effect)].

Effects of saccharose or invert sugar on kinetics of lipid synthesis in the rat liver were investigated using 1-14C-glucose as a precursor. The diet containing 30% of saccharose (of the total energy value) for 40 days was found to be sufficient to increase the radioactive carbon flux through total liver lipids more than twice, and through rapidly metabolized neutral lipids and phospholipids more than 4 and 3 times, consequently. On the contrary, when the invert sugar diet was used the radioactive carbon flux through total lipids in the liver was reduced up to 54% of the control level, the lowest radioactive carbon flux was observed through the rapidly metabolized fraction of phospholipids--6% of the control level, only. These changes were caused by the corresponding alterations in lipid synthesis constants.

Animals↗
PubMed1979

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

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 non- and 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-O-(beta-D-glucopyranosyluronic acid)-2,5-anhydro-D-mannitol and 4-O-(alpha-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 of the corresponding unlabelled disaccharides, permitted the allocation of O-sulphate groups to various positions in the disaccharides. These were thus identified as 4-O-(beta-D-glucopyranosyl-uronic acid)-2,5-anhydro-D-mannitol 6-sulphate, 4-O-(alpha-L-idopyranosyluronic acid)-2,5-anhydro-D-mannitol 6-sulphate and 4-O-(alpha-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-O-(alpha-L-idopyranosyluronic acid 2-sulphate)-2,5-anhydro-D-mannitol 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 heparin 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 O-sulphate substituents.

Chemical Phenomena↗
PubMed1994

Determination of 24 variously sulfated galactosaminoglycan- and hyaluronan-derived disaccharides by high-performance liquid chromatography.

In this report we describe a very sensitive high-performance liquid chromatographic method for the determination of 24 nonsulfated and variously sulfated disaccharides present in chondroitin sulfates, dermatan sulfates, and hyaluronic acid. The method is superior to others in that monosulfated disaccharides at either C-2 or C-3 of the uronic acid moieties and mono-, di-, and trisulfated disaccharides containing N-sulfated galactosamine as well as non-, mono-, and oversulfated disaccharides derived from iduronic acid can be determined. Following chondroitinase digestions of tissue extracts or purified hyaluronic acid, chondroitin sulfate, and dermatan sulfate, the non-, di-, and trisulfate delta-disaccharides, are separated by direct injections into HPLC, whereas the monosulfated delta-disaccharides are chromatographed after a simple reduction of the galactosamine carbonyl group with sodium borohydride. The various sulfated delta-disaccharides are separated on an amino column (Econosphere NH2) and recorded at 231 nm. The column is eluted isocratically with 5 mM sodium dihydrogen orthophosphate, pH 2.55, for nonsulfated delta-disaccharides; 50 mM sodium dihydrogen orthophosphate, pH 2.50, for reduced monosulfated; and 50 mM sodium sulfate-10 mM sodium acetate, pH 5.0, for the separation of di- and trisulfated delta-disaccharides. A linear detector response was obtained for injections up to 50 micrograms of delta-disaccharides. As little as 5-8 ng of nonsulfated, 8-11 ng of monosulfated, 12-15 ng of disulfated, and 25-30 ng of trisulfated delta-disaccharides can be reliably detected. Application of this HPLC method to the analysis of various glycosaminoglycans in conjunction with chondroitinase AC, ABC, or B digestions and sulfatase hydrolysis adds to the knowledge of the structural spectrum of the galactosaminoglycans. It was thus possible to identify 24 different disaccharides in chondroitinase-susceptible glycosaminoglycans, including all C-5 epimeric disaccharides and those sulfated at C-2 or C-3 of the uronic acids and at the amino group of the galactosamine.

Animals↗
PubMed1997

Ion-pair high-performance liquid chromatography for determining disaccharide composition in heparin and heparan sulphate.

In this report we describe a convenient and sensitive HPLC method for separating and determining the non- and variously sulphated delta-disaccharides derived from heparan sulphate, heparin and Fragmin, using heparin- and heparan sulphate lyases. This method is superior to others since it can separate and determine twelve different non-, mono-, di- and trisulphated delta-disaccharides containing either N-sulphated, N-acetylated or unsubstituted glucosamine in a single HPLC run. The various types of delta-disaccharides are separated by an ion-pair reversed-phase chromatographic procedure on a Supelcosil LC-18 column, using a binary acetonitrile gradient system with tetrabutylammonium as the ion-pairing reagent. The eluted peaks were recorded by dual wavelength at 232 and 226 nm and a linear detector response was obtained over the entire interval tested, i.e., to 50 micrograms of delta-disaccharides. As little as 0.8-5 ng of delta-disaccharides can be reliably detected and accurately determined. Following separate digestion with the heparin- and heparan sulphate lyases (heparin lyases I, II and III), the characteristic heparin delta-disaccharides in the heparan sulphate chain, as well as the heparan sulphate delta-disaccharides in the heparin polymer, can be identified. Using combined digestions with these three lyases, the glycosaminoglycan chains are degraded almost completely (> 90%) to delta-disaccharides, which are then determined by direct injections into the HPLC system and thus an almost complete spectrum of disaccharide composition can be obtained. By this method, it is possible to analyse and confirm that the heparan sulphate chain is defined as a glycosaminoglycan dominated by GlcNAc(+/- 6S)-GlcA disaccharides and by some copolymeric disaccharides, such as GlcNS-IdoA2S and GlcNS6S-IdoA2S, otherwise most common in heparin. Fragmin, which is a controlled cepolymerized heparin fragment of M(r) 5000, is made up mainly of trisulphated disaccharides of the GlcNS6S-IdoA2S type (88.8%). Using separate digestions with the specific heparin lyases, one can also distinguish between heparin and heparan sulphate.

Acetonitriles↗
PubMed2001

Disaccharides derived from heparin or heparan sulfate regulate IL-8 and IL-1 beta secretion by intestinal epithelial cells.

BACKGROUND & AIMS: Intestinal epithelial cells can produce cytokines and chemokines that play an important role in the mucosal immune response. Regulation of this secretion is important to prevent inflammatory tissue damage. Disaccharides derived from heparan sulfate and heparin have been shown to down-regulate inflammation in vivo. We tested the effect of such disaccharides on cytokine secretion by intestinal epithelial cells. METHODS: Spontaneous and tumor necrosis factor (TNF)-alpha-stimulated interleukin (IL)-8 and IL-1 beta secretion and mRNA expression were assessed in HT-29 and Caco-2 intestinal epithelial cell lines in the presence of a panel of heparin and heparan sulfate disaccharides. RESULTS: Specific disaccharides suppressed spontaneous and TNF-alpha-induced mediator secretion in a dose-dependent manner. Disaccharide activity was structurally restricted. Preincubation of cells with nonsuppressing disaccharides blocked the activity of suppressing disaccharides. The number of sulfate moieties determined the ability of nonsuppressing disaccharides to block the effect of suppressive disaccharides. No suppression of mRNA expression was noted, and intracellular mediator levels were not reduced. CONCLUSIONS: Disaccharides derived from heparin and heparan sulfate regulate proinflammatory mediator secretion from intestinal epithelial cells. Dose dependence and competition by structurally diverging disaccharides suggest a receptor-mediated mechanism. Unchanged mRNA and intracellular mediator levels suggest that the disaccharides act at posttranscriptional stages.

Adjuvants, Immunologic↗