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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↗
PubMed2006

A novel glycoside hydrolase family 105: the structure of family 105 unsaturated rhamnogalacturonyl hydrolase complexed with a disaccharide in comparison with family 88 enzyme complexed with the disaccharide.

YteR, a hypothetical protein with unknown functions, is derived from Bacillus subtilis strain 168 and has an overall structure similar to that of bacterial unsaturated glucuronyl hydrolase (UGL), although it exhibits little amino acid sequence identity with UGL. UGL releases unsaturated glucuronic acid from glycosaminoglycan treated with glycosaminoglycan lyases. The amino acid sequence of YteR shows a significant homology (26% identity) with the hypothetical protein YesR also from B. subtilis strain 168. To clarify the intrinsic functions of YteR and YesR, both proteins were overexpressed in Escherichia coli, purified, and characterized. Based on their gene arrangements in genome and enzyme properties, YteR and YesR were found to constitute a novel enzyme activity, "unsaturated rhamnogalacturonyl hydrolase," classified as new glycoside hydrolase family 105. This enzyme acts specifically on unsaturated rhamnogalacturonan (RG) obtained from RG type-I treated with RG lyases and releases an unsaturated galacturonic acid. The crystal structure of YteR complexed with unsaturated chondroitin disaccharide (UGL substrate) was obtained and compared to the structure of UGL complexed with the same disaccharide. The UGL substrate is sterically hindered with the active pocket of YteR. The protruding loop of YteR prevents the UGL substrate from being bound effectively. The most likely candidate catalytic residues for general acid/base are Asp143 in YteR and Asp135 in YesR. This is supported by three-dimensional structural and site-directed mutagenesis studies. These findings provide molecular insights into novel enzyme catalysis and sequential reaction mechanisms involved in RG-I depolymerization by bacteria.

Acetylglucosamine↗
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↗
PubMed2000

Enzymatic synthesis of novel disaccharides using disaccharide phosphorylases.

A method for the synthesis of novel disaccharides was developed. It involved the following two steps. The first step consisted of two continuous reactions: the conversion of maltose to beta-D-glucose-1-phosphate and D-glucose by the phosphorolytic activity of maltose phosphorylase and the specific consumption of only D-glucose by incubation with glucose-consuming yeast cells. The second step involved the addition of an appropriate carbohydrate and its condensation with the remaining beta-D-glucose-1-phosphate by the synthetic activity of maltose phosphorylase or trehalose phosphorylase. Several factors affecting the yields of disaccharides were optimized. Using this method, five maltose-like derivatives and two trehalose-like derivatives were synthesized from maltose and the corresponding carbohydrates. Among these, 4-O-alpha-D-glucopyranosyl-L-fucopyranose (Glc(alpha1-4)Fuc) and alpha-d-glucopyranosyl alpha-D-fucopyranoside (Glc(alpha1-1alpha)Fuc) were purified, and identified by 1H NMR and 13C NMR.

Journal Article↗
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↗