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Search for "oligosaccharides" in Full Text gives 179 result(s) in Beilstein Journal of Organic Chemistry.
Synthesis of multi-lactose-appended β-cyclodextrin and its cholesterol-lowering effects in Niemann–Pick type C disease-like HepG2 cells
Beilstein J. Org. Chem. 2017, 13, 10–18, doi:10.3762/bjoc.13.2
- children, results in severe hepatosplenomegaly and neurodegeneration [3][6]. Hence, the sequestration of cholesterol is an important factor in the development of the NPC disease. Cyclodextrins (CDs) are cyclic glucose oligosaccharides used by the pharmaceutical industry to enhance solubility, stability
Stabilization of nanosized titanium dioxide by cyclodextrin polymers and its photocatalytic effect on the degradation of wastewater pollutants
Beilstein J. Org. Chem. 2016, 12, 2873–2882, doi:10.3762/bjoc.12.286
- oligosaccharides consisting of 6–8 glucose units (α-, β- and γ-CD) primarily used in the pharmaceutical, cosmetic and household chemical industry [8]. They form non-covalent inclusion complexes with a great number of the organic contaminants in soil (petroleum hydrocarbons, polycyclic aromatic hydrocarbons, etc
O-Alkylated heavy atom carbohydrate probes for protein X-ray crystallography: Studies towards the synthesis of methyl 2-O-methyl-L-selenofucopyranoside
Beilstein J. Org. Chem. 2016, 12, 2828–2833, doi:10.3762/bjoc.12.282
- are used as reactive glycosyl donors in the syntheses of oligosaccharides. In addition, such heavy atom analogs of natural glycosides are useful tools for structure determination of their lectin receptors using X-ray crystallography. Some lectins, e.g., members of the tectonin family, only bind to
- derivatives are nowadays used as powerful tools in organic chemistry [6]. Synthetic selenoglycosides are versatile synthons in glycosylation reactions as glycosyl donors for the synthesis of glycosides and oligosaccharides, where their aglycon acts as a leaving group [7][8][9]. They can be selectively
Synthesis and NMR studies of malonyl-linked glycoconjugates of N-(2-aminoethyl)glycine. Building blocks for the construction of combinatorial glycopeptide libraries
Beilstein J. Org. Chem. 2016, 12, 1939–1948, doi:10.3762/bjoc.12.183
- specific glycoconjugates from natural sources remains a difficult, sometimes even an unrealizable task, for naturally occurring saccharides exhibit micro-heterogenity which makes it nearly impossible to obtain pure material from such sources. Chemical or chemoenzymatic syntheses of complex oligosaccharides
- , on the other hand, may provide sufficient amounts of pure material for such studies. Despite the great achievements in oligosaccharide synthesis during the past decades, the preparation of complex oligosaccharides can be tedious, lengthy or circuitous, and the often intrinsic intricacy of a chemical
Cross-linked cyclodextrin-based material for treatment of metals and organic substances present in industrial discharge waters
Beilstein J. Org. Chem. 2016, 12, 1826–1838, doi:10.3762/bjoc.12.172
- properties leading to a host–guest relationship with organic substances [6][7][8][9]. These cyclic oligosaccharides are water soluble in their native form and are often modified to prepare novel insoluble CD-based materials. Two patents published by Martel et al. [10], and Trotta et al. [11] can be consulted
TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
Beilstein J. Org. Chem. 2016, 12, 1758–1764, doi:10.3762/bjoc.12.164
- [4], and were recently observed to inhibit cancer growth [5]. Because of the relevance of 2-deoxyglycosides, great efforts have been made in researching the assembly of oligosaccharides containing these sugars [6][7]. However, the absence of a neighbouring group at C2 causes poor stereoselectivity
- anomeric mixtures [10]. Glycals have been considered as alternative precursors for producing 2-deoxythioglycosides as well as oligosaccharides. Several methods based on the use of glycals in the presence of Lewis acids for S- or O-2-deoxyglycoside preparations have been developed [51][52][53][54][55][56
Automated glycan assembly of a S. pneumoniae serotype 3 CPS antigen
Beilstein J. Org. Chem. 2016, 12, 1440–1446, doi:10.3762/bjoc.12.139
- step with the activator prior to each glycosylation cycle greatly increased the yields by neutralizing any residual base from deprotection steps in the synthetic cycle. This process improvement is applicable to AGA of many other oligosaccharides. Keywords: automation; glycosylation; protecting groups
- ; oligosaccharides; solid-phase synthesis; Streptococcus pneumoniae; Introduction The Gram-positive encapsulated commensal bacterium Streptococcus pneumoniae [1][2][3] can cause serious medical conditions like pneumonia, meningitis, endocarditis and sepsis [4]. S. pneumoniae is the leading cause of vaccine
- containing oligosaccharides of different lengths and frame shifts [19]. Synthetic oligosaccharide antigens enable structure–activity relationship (SAR) studies of bacterial antigens [20] to better understand antibody binding and help to improve existing vaccine formulations. Two synthetic routes to prepare
Mutagenic activity of quaternary ammonium salt derivatives of carbohydrates
Beilstein J. Org. Chem. 2016, 12, 1434–1439, doi:10.3762/bjoc.12.138
- . The polymers (oligosaccharides) of D-glucose found, for example, in wood (cellulose) and D-glucosamine present in shells of crabs and insects (chitin), are the widely known ones [1][2]. Another class of carbohydrate biopolymer derivatives – D-ribose and 2-deoxy-D-ribose – constitutes the backbone of
Synthesis and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine
Beilstein J. Org. Chem. 2016, 12, 750–759, doi:10.3762/bjoc.12.75
- analogs 6–8 are new compounds and their influence on the cell-surface glycan biosynthesis is currently being studied. We anticipate that 1,6-anhydro-2-azido-fluorohydrins 20, 21, 26 and 31 will find use as building blocks for the synthesis of fluorinated oligosaccharides and other glycoconjugates because
Elucidation of a masked repeating structure of the O-specific polysaccharide of the halotolerant soil bacteria Azospirillum halopraeferens Au4
Beilstein J. Org. Chem. 2016, 12, 636–642, doi:10.3762/bjoc.12.62
- above), elimination of the side-chain Glc and cleavage of the linkage of the destroyed 2-substituted Xyl were expected. Fractionation of the Smith degradation products by TSK HW-40 (S) gel-permeation chromatography resulted in a mixture of the expected oligosaccharides 1 and 2 and higher molecular mass
- published data δ 72.3 and 76.8 for α- and β-Glc, respectively [19]. The 4-substitution of Fuc was inferred from a significantly downfield shift to δ 82.1–83.0 of the C-4 signal as compared with its positions in the non-substituted α-Fuc at δ 72.9 [19]. Combining structural data of the oligosaccharides 1–3
- afforded complementary oligosaccharides, which identification shed light on the nature of the OPS irregularity and, combined with chemical analysis and NMR spectroscopic analysis data, enabled the structure elucidation of the OPS. Chemical modifications of the OPS, such as O-methylation or O-acetylation
Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions
Beilstein J. Org. Chem. 2016, 12, 549–563, doi:10.3762/bjoc.12.54
- ][6][7]. CDs are a family of cyclic oligosaccharides and different members of this family have been used widely for several years. More specifically, CDs are manufactured from starch, a polymer with D-glucopyranoside building blocks with both α-1,4- and α-1,6-glycosidic linkages [8]. The most common
New synthetic strategies for xanthene-dye-appended cyclodextrins
Beilstein J. Org. Chem. 2016, 12, 537–548, doi:10.3762/bjoc.12.53
- supramolecular assembly of the xanthene-dye-appended cyclodextrins were developed based on the set of data collected by the extensive NMR characterization. Keywords: DMT-MM; fluorescein; rhodamine; supramolecular assembly; Introduction Cyclodextrins (CDs) are cyclic oligosaccharides consisting of 6, 7 or 8
Enabling technologies and green processes in cyclodextrin chemistry
Beilstein J. Org. Chem. 2016, 12, 278–294, doi:10.3762/bjoc.12.30
- environment only. The secondary carbon substitution results in inversion in the reaction centre which changes the sugar moiety from glucoside to mannoside, altroside or alloside making those derivatives CD-based cyclic oligosaccharides and not CDs. The design of green synthetic methods for the bulk
- Vijayalakshmi have pointed out the theoretical use of enzymes in the production of CDs or other cyclic oligosaccharides, like cyclofructan, rather than using a microreactor [104]. Conclusion Dynamic intrusion of the enabling technologies to the CD chemistry is inevitable and shows exponential growth. Although
Interactions of cyclodextrins and their derivatives with toxic organophosphorus compounds
Beilstein J. Org. Chem. 2016, 12, 204–228, doi:10.3762/bjoc.12.23
- ) the hydrolysis of the nerve agents by CDs under specific conditions; (3) the selective modifications of these cyclic oligosaccharides to improve their hydrolytic efficiency at physiological pH and temperature. Review Inclusion studies between CDs and pesticides Due to their toroidal structure, CDs are
- cyclic oligosaccharides. As CDs exhibit a large number of primary (C-6 position of glucose units) and secondary (C-2 and C-3 positions) alcohols, selective modifications are therefore difficult. Most of them are based on the slight differences in the reactivity of these three kinds of hydroxy groups. In
Thermal and oxidative stability of Atlantic salmon oil (Salmo salar L.) and complexation with β-cyclodextrin
Beilstein J. Org. Chem. 2016, 12, 179–191, doi:10.3762/bjoc.12.20
- -containing microcapsules [27][33] and spontaneous emulsification for obtaining nanoemulsions [20][31][32]. One nanoencapsulation method of fish oil components is the molecular encapsulation in cyclodextrins (CDs). The latter are natural or synthetically modified, cyclic oligosaccharides comprising 6, 7, and
Supramolecular polymer assembly in aqueous solution arising from cyclodextrin host–guest complexation
Beilstein J. Org. Chem. 2016, 12, 50–72, doi:10.3762/bjoc.12.7
- ], chemical sensors [6] and drug delivery [7][8][9]. As discussed in a range of reviews [10][11][12][13][14] and books [15][16][17][18], cyclodextrins are naturally occurring cyclic oligosaccharides which are also produced industrially through the enzymatic metabolism of starch and related compounds. The
Determination of formation constants and structural characterization of cyclodextrin inclusion complexes with two phenolic isomers: carvacrol and thymol
Beilstein J. Org. Chem. 2016, 12, 29–42, doi:10.3762/bjoc.12.5
- cyclic oligosaccharides. The common native CDs contain 6, 7 and 8 D-(+)-glucopyranose units bound together by α(1→4) linkages and are referred to as α-, β- and γ-CDs [21]. The chair conformation of the glucose units results in a truncated shape of CDs with an external hydrophilic surface and a
Assembly of synthetic Aβ miniamyloids on polyol templates
Beilstein J. Org. Chem. 2015, 11, 2646–2653, doi:10.3762/bjoc.11.284
- diols on the template must be separated from each other far enough to exclude the simultaneous formation of mixtures of 5- and 6-membered boronic esters. However, the oligosaccharides, which are available with a consistent oligomerization degree of dimer, trimer, tetramer and higher, are known to have
Preparation of Pickering emulsions through interfacial adsorption by soft cyclodextrin nanogels
Beilstein J. Org. Chem. 2015, 11, 2355–2364, doi:10.3762/bjoc.11.257
- oligosaccharides, which have subnanometer-sized cavities where guest molecules with an appropriate size and shape are incorporated [10]. CDs have been reported to work as emulsion stabilizers [11][12][13][14]. Previous studies have shown that CDs can form surface-active inclusion complexes with oil molecules at
Co-solvation effect on the binding mode of the α-mangostin/β-cyclodextrin inclusion complex
Beilstein J. Org. Chem. 2015, 11, 2306–2317, doi:10.3762/bjoc.11.251
- addition [2][3][4][5][6][7][8] and surfactant addition [9]. Complexation is one of the most utilized methods for enhancing the solubility of poorly soluble drugs. Cyclodextrins (CDs) are well-known macrocyclic oligosaccharides that are produced by enzymatic degradation of starch. CDs consist of 6, 7 and 8
Cholesterol lowering effects of mono-lactose-appended β-cyclodextrin in Niemann–Pick type C disease-like HepG2 cells
Beilstein J. Org. Chem. 2015, 11, 2079–2086, doi:10.3762/bjoc.11.224
- cholesterol sequestration is found to be a crucial factor in developing NPC disease. Cyclodextrins (CyDs) are non-reducing cyclic glucose oligosaccharides obtained by enzymatic means from starch-containing raw materials and have been used for the enhancement of drugs solubility, stability and bioavailability
Effective ascorbate-free and photolatent click reactions in water using a photoreducible copper(II)-ethylenediamine precatalyst
Beilstein J. Org. Chem. 2015, 11, 1950–1959, doi:10.3762/bjoc.11.211
- such transformations are: (i) high copper loading, often used in excess with respect to the substrates, due to limited catalyst reactivity and the fact that the substrates (proteins, oligonucleotides or oligosaccharides) are typically used in dilute conditions; (ii) contamination of the products by
Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners
Beilstein J. Org. Chem. 2015, 11, 1922–1932, doi:10.3762/bjoc.11.208
- singlet at δ = 7.78 ppm confirming the cycloaddition of derivatives 3 and 10. D-Glucosamine is an essential constituent of many naturally occurring oligosaccharides such as bacterial and fungal cell walls. Mainly, it is available as N-acetylglucosamine in β-glycosidic linkages (β-D-GlcNAc) [37
Profluorescent substrates for the screening of olefin metathesis catalysts
Beilstein J. Org. Chem. 2015, 11, 1886–1892, doi:10.3762/bjoc.11.203
- quencher are disconnected resulting in the fluorescent product 7. A similar linker concept has previously been implemented for a solid-phase linker in the synthesis of oligosaccharides [18][19]. The second profluorescent molecule selected was diolefin 8, which yields fluorescent 7-hydroxycoumarin
Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives
Beilstein J. Org. Chem. 2015, 11, 1547–1552, doi:10.3762/bjoc.11.170
- of enzymes that are responsible for the biosynthesis of complex oligosaccharides, glycoproteins and other glycoconjugates in mammalian biological systems. These glycoconjugates are operating in the cell and on the cell surface, particularly as glycoproteins, and are involved in many vital biological
- unknown [7]. In general, GTs transfer sugar nucleotide donors onto suitable acceptors during the biosynthesis of glycans and glycoconjugates [8]. Both donor and acceptor substrates are recognized by GTs binding pockets. For instance, in the course of biosynthesis of complex and hybrid oligosaccharides
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