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Chemical Communications (Cambridge,... Nov 2015We reported a three-component smart polymer, which could discriminate disaccharide homologues and translate the recognition signals into distinct differences in the...
We reported a three-component smart polymer, which could discriminate disaccharide homologues and translate the recognition signals into distinct differences in the macroscopic properties (i.e. wettability and adhesion force) of materials. With these features, we further showed its application in glycopeptide enrichment.
Topics: Disaccharides; Glycopeptides; Molecular Structure; Quantum Theory; Spectrometry, Mass, Electrospray Ionization; Surface Properties; Wettability
PubMed: 26394215
DOI: 10.1039/c5cc06279a -
Bioscience, Biotechnology, and... Sep 2000D-Galactosyl-alpha-1,3-D-galactopyranose (1) was chemically prepared in a good yield by coupling phenyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside (5) or...
Practical synthesis of the disaccharide epitope, D-galactopyranosyl-alpha-1,3-D-galactopyranose, by using 1,2;5,6-di-O-cyclohexylidene-alpha-D-galactofuranose as the glycosyl acceptor.
D-Galactosyl-alpha-1,3-D-galactopyranose (1) was chemically prepared in a good yield by coupling phenyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside (5) or 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl bromide (8) with 1,2:5,6-di-O-cyclohexylidene-alpha-D-galactofuranose (3) with subsequent de-O-benzylation and de-O-cyclohexylidenation of the resulting protected alpha1,3-disaccharide.
Topics: Carbohydrate Conformation; Disaccharides; Epitopes; Galactose; Indicators and Reagents; Models, Molecular
PubMed: 11055406
DOI: 10.1271/bbb.64.1974 -
Cell and Tissue Research Feb 1999Carbohydrate residues contained in the zona pellucida play a key role in the process of sperm-egg interaction. In vitro fertilization experiments have shown that a...
Carbohydrate residues contained in the zona pellucida play a key role in the process of sperm-egg interaction. In vitro fertilization experiments have shown that a specific monoclonal antibody against GalNAcbeta1,4Galbeta1,4 disaccharide inhibits fertilization in mice. In the present study, the ultrastructural cytochemical localization of GalNAc residues and the GalNAcbeta1,4Galbeta1,4 disaccharide was carried out in ovarian and postovulatory oocytes by using lectin-gold cytochemistry and immunocytochemistry. Plant lectins SBA and DBA showed an affinity for the entire zona pellucida matrix of ovarian oocytes throughout the follicular maturation; however, immunoreactivity for GalNAcbeta1,4Galbeta1,4 disaccharide was not detected in ovarian oocytes at the earliest stages of follicular development but was found to be associated with the inner region of the zona matrix at the trilaminar primary follicle stage. The Golgi apparatus, vesicular aggregates, and cortical granules of the oocyte were intensely labeled by SBA and DBA throughout follicular development. Immunoreactivity to GalNAcbeta1,4Galbeta1,4 disaccharide was first observed in the Golgi apparatus and vesicular aggregates in trilaminar primary follicles. No immunoreactivity was observed in the cortical granules. In postovulatory oocytes, results were similar to those observed in ovarian oocytes. Our results thus suggest that (1) GalNAcbeta1,4Galbeta1,4 disaccharide residues are present only in the inner region of the zona pellucida and, therefore, might be involved in sperm penetration through the zona pellucida, (2) the inner and outer regions of the zona pellucida contain different oligosaccharide chains, (3) the vesicular aggregates detected in the oocyte could represent an intermediate step in the secretory pathway of zona pellucida glycoproteins and might be involved in the formation of cortical granules.
Topics: Animals; Disaccharides; Female; Histocytochemistry; Mice; Microscopy, Electron; N-Acetylgalactosaminyltransferases; Zona Pellucida
PubMed: 9931373
DOI: 10.1007/s004410051233 -
Glycoconjugate Journal Apr 2017The development of an immuno-PCR assay for quantitation of low amounts of anti-glycan human antibodies is described. The sensitivity of the assay for determination of...
The development of an immuno-PCR assay for quantitation of low amounts of anti-glycan human antibodies is described. The sensitivity of the assay for determination of low-affinity anti-Le IgM has been found to be 4 ng/ml (~100 pg per sample), thus being two orders of magnitude higher compared to the conventional ELISA with the same antigen.
Topics: Disaccharides; Humans; Immunoglobulin M; Polymerase Chain Reaction
PubMed: 28091939
DOI: 10.1007/s10719-016-9751-6 -
Carbohydrate Research Oct 1993Methyl 2,6-dideoxy-4-O-[2,6-dideoxy-4-O-(3,5-dichloro-4-hydroxy-2-methoxy-6- methylbenzoyl)-beta-D-arabino-hexopyranosyl]-alpha-D-arabino-he xopyranoside (25)...
Methyl 2,6-dideoxy-4-O-[2,6-dideoxy-4-O-(3,5-dichloro-4-hydroxy-2-methoxy-6- methylbenzoyl)-beta-D-arabino-hexopyranosyl]-alpha-D-arabino-he xopyranoside (25) corresponds to an A-B-C disaccharide subunit of the title antibiotics. It was synthesized from suitably protected monosaccharide and aromatic precursors. The readily available 4,6-O-benzylidene-1,2-O-(R)-propylidene-alpha-D-glucopyranose was converted in six steps into 2-O-acetyl-4-O-benzoyl-3-O-benzyl-6-deoxy-alpha-D-glucopyranosyl bromide, which was condensed with methyl 3-O-benzyl-2,6-dideoxy-alpha-D-arabino-hexopyranoside in the presence of mercury(II) cyanide. Methyl 4-O-(2-O-acetyl-4-O-benzoyl-3-O-benzyl-6-deoxy-beta- D-glucopyranosyl)-3-O-benzyl-2,6-dideoxy-alpha-D-arabino-hexopyranosi de was converted either into methyl 2,6-dideoxy-4-O-(6-deoxy-beta-D- glucopyranosyl)-alpha-D-arabino-hexopyranoside by removal of the protective groups or into methyl 3-O-benzyl-4-O-(3-O-benzyl-2,6-dideoxy-beta-D-arabino-hexopyranosyl)-2,6 - dideoxy-alpha-D-arabino-hexopyranoside (22) by selective deacetylation, Barton deoxygenation, and Zemplén debenzoylation. Disaccharide 22 was deprotonated with butyllithium and treated with 4-benzyloxy-3,5-dichloro-2-methoxy-6-methylbenzoyl chloride to give the title compound 25 after hydrogenolysis.
Topics: Anti-Bacterial Agents; Carbohydrate Conformation; Carbohydrate Sequence; Disaccharides; Indicators and Reagents; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Sequence Data; Oligosaccharides; Optical Rotation
PubMed: 8252527
DOI: 10.1016/0008-6215(93)84119-q -
Drugs Jun 1997Lactulose is one of the most frequently utilised agents in the treatment of constipation and hepatic encephalopathy because of its efficacy and good safety profile. The... (Review)
Review
Lactulose is one of the most frequently utilised agents in the treatment of constipation and hepatic encephalopathy because of its efficacy and good safety profile. The key to understanding the possible modes of action by which lactulose achieves its therapeutic effects in these disorders lies in certain pharmacological phenomena: (a) lactulose is a synthetic disaccharide that does not occur naturally; (b) there is no disaccharidase on the microvillus membrane of enterocytes in the human small intestine that hydrolyses lactulose; and (c) lactulose is not absorbed from the small intestine. Thus, the primary site of action is the colon in which lactulose is readily fermented by the colonic bacterial flora with the production of short-chain fatty acids and various gases. The purpose of this review is to focus on some pertinent basic aspects of the clinical pharmacology of lactulose and to discuss the possible mechanisms by which lactulose benefits patients with constipation and hepatic encephalopathy.
Topics: Animals; Cathartics; Colon; Constipation; Disaccharides; Gastrointestinal Agents; Hepatic Encephalopathy; Humans; Lactulose
PubMed: 9179525
DOI: 10.2165/00003495-199753060-00003 -
Journal of Enzyme Inhibition and... Dec 2018A new class of tyrosyl-DNA phosphodiesterase 1 (TDP1) inhibitors based on disaccharide nucleosides was identified. TDP1 plays an essential role in the resistance of...
A new class of tyrosyl-DNA phosphodiesterase 1 (TDP1) inhibitors based on disaccharide nucleosides was identified. TDP1 plays an essential role in the resistance of cancer cells to currently used antitumour drugs based on Top1 inhibitors such as topotecan and irinotecan. The most effective inhibitors investigated in this study have IC values (half-maximal inhibitory concentration) in 0.4-18.5 µM range and demonstrate relatively low own cytotoxicity along with significant synergistic effect in combination with anti-cancer drug topotecan. Moreover, kinetic parameters of the enzymatic reaction and fluorescence anisotropy were measured using different types of DNA-biosensors to give a sufficient insight into the mechanism of inhibitor's action.
Topics: Antineoplastic Agents; Cell Proliferation; Cells, Cultured; Disaccharides; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Humans; Molecular Structure; Nucleosides; Phosphodiesterase Inhibitors; Phosphoric Diester Hydrolases; Structure-Activity Relationship; Topotecan
PubMed: 30191738
DOI: 10.1080/14756366.2018.1509210 -
Bioseparation 2001The selectivity of carbohydrate-imprinted polymers for several disaccharides, namely cellobiose, maltose, lactose and gentiobiose, is investigated. An ternary...
The selectivity of carbohydrate-imprinted polymers for several disaccharides, namely cellobiose, maltose, lactose and gentiobiose, is investigated. An ternary ligand-Cu(II)-carbohydrate complex was formed in alkaline solution and captured afterwards in the polymer. The accessibility of the polymer matrix for disaccharides was investigated by HPLC analysis, refractometry and 1H NMR spectroscopy applying excess of the original template during rebinding experiments under saturation conditions in unbuffered, aqueous solution at neutral pH and 20 degrees C. The selective discrimination of the alpha- and beta-glycosidic linkage of cellobiose and maltose is demonstrated. It is further shown, that the disaccharide-imprinted polymers slightly distinguish between the 1,4-beta- and the 1,6-beta-glycosidic linkage of cellobiose and gentiobiose, while cellobiose and lactose are not selectively recognized. Due to the weak apparent binding constant of the functional Cu(II) monomers with the targeted disaccharides at physiological pH, the recognition process is dominated by the shape of the created imprinted cavity under the applied conditions.
Topics: Carbohydrate Sequence; Chromatography, High Pressure Liquid; Disaccharides; Magnetic Resonance Spectroscopy; Polymers; Refractometry; Spectrophotometry, Ultraviolet
PubMed: 12549874
DOI: 10.1023/a:1021589619501 -
Carbohydrate Research Dec 2020The indium-mediated allylation followed by ozonolysis has been applied for the elongation of different disaccharides such as cellobiose, lactose and maltose. This...
The indium-mediated allylation followed by ozonolysis has been applied for the elongation of different disaccharides such as cellobiose, lactose and maltose. This reaction sequence and per-O-acetylation produced the expected mixture of α/β-pyranoid as well as α/β-furanoid isomers. The main product in all cases adopted the β-pyranose form and could be isolated and fully characterized with the help of NMR-spin simulations. Thorough investigation of the side products throughout optimization of the conditions for the ozonolysis resulted in the discovery of a novel 12 membered bridged disaccharide.
Topics: Alkenes; Catalysis; Disaccharides; Indium; Isomerism; Ozone
PubMed: 33068775
DOI: 10.1016/j.carres.2020.108170 -
Carbohydrate Research Jul 2012An orthogonally protected disaccharide (GlcN(α1→4)Glc) with a β-linked 2'-aminoethyl linker was used to generate a series of sulfated derivatives (sulfoforms), with...
An orthogonally protected disaccharide (GlcN(α1→4)Glc) with a β-linked 2'-aminoethyl linker was used to generate a series of sulfated derivatives (sulfoforms), with a 6-O-sulfate on the glucose residue and one or more sulfate esters on the terminal glucosamine. Deprotection and sulfonation steps were performed in solution and in variable order, with isolated yields of 36-54% (85-90% per operation) after HPLC purification. The modular deprotection-sulfonation sequences can be performed with efficient recovery of the polysulfate products, and avoids complications associated with heterogeneous reactivity in solid-phase synthesis.
Topics: Chromatography, High Pressure Liquid; Disaccharides; Molecular Conformation; Sulfur Compounds
PubMed: 22624867
DOI: 10.1016/j.carres.2012.04.010