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Search for "oligosaccharides" in Full Text gives 169 result(s) in Beilstein Journal of Organic Chemistry.
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
Automated solid-phase synthesis of oligosaccharides containing sialic acids
Beilstein J. Org. Chem. 2015, 11, 617–621, doi:10.3762/bjoc.11.69
- 10.3762/bjoc.11.69 Abstract A sialic acid glycosyl phosphate building block was designed and synthesized. This building block was used to prepare α-sialylated oligosaccharides by automated solid-phase synthesis selectively. Keywords: α-sialylation; automated synthesis; glycosylation; sialic acid; solid
- carbohydrate antigens (TACAs) such as the sialyl-Tn antigen (sTn) [2]. Neu5Ac is often the terminal residue and is usually linked via an α-(2,3) or α-(2,6) linkage to galactose (Gal) (Figure 1) [3]. Automated glycan assembly enables rapid access to structurally defined oligosaccharides [4][5] including
- incorporation of sialic acid–galactose disaccharide building blocks [5][11]. Here, we describe a sialic acid building block that can be utilized for automated glycan assembly. Results and Discussion Sialylating oligosaccharides in high yield and α-selectivity was challenging since the presence of a C-1 carboxyl
Synthesis of a hexasaccharide partial sequence of hyaluronan for click chemistry and more
Beilstein J. Org. Chem. 2015, 11, 604–607, doi:10.3762/bjoc.11.67
- fragments which were bearing either a free reducing end or a non-functionalized aglycone [16][17][18]. In 2007, a study focusing on the synthesis of HA sequences which could be functionalized and used for biological studies yielded oligosaccharides bearing an alkyl-azide [19]. Besides the results of this
- linkages; most important was the reaction's stereochemical outcome. Elongation of the synthesized oligosaccharides was easily done, since the TBS-protection is selectively cleavable. The anomeric allyl moiety permits varieties of feasible modifications including the introduction of an azido group. In the
Formulation development, stability and anticancer efficacy of core-shell cyclodextrin nanocapsules for oral chemotherapy with camptothecin
Beilstein J. Org. Chem. 2015, 11, 204–212, doi:10.3762/bjoc.11.22
- CPT for cancer therapy. CDs can be a means of overcoming these problems for the in vivo behaviour of CPT upon intravenous or oral administration. CDs are natural polymers which are produced from enzymatic degradation of starch [23]. They are cyclic oligosaccharides and consist of at least 6 D
Effects of RAMEA-complexed polyunsaturated fatty acids on the response of human dendritic cells to inflammatory signals
Beilstein J. Org. Chem. 2014, 10, 3152–3160, doi:10.3762/bjoc.10.332
- ethanol, because they could not be dissolved in water owing to their long alkyl chains. However, solubilization of PUFAs could also be achieved by aqueous cyclodextrin (CD) solutions, which allowed us to avoid organic solvents. CDs are cyclic oligosaccharides consisting of 6, 7 or 8 glucopyranose units (α
Release of β-galactosidase from poloxamine/α-cyclodextrin hydrogels
Beilstein J. Org. Chem. 2014, 10, 3127–3135, doi:10.3762/bjoc.10.330
- group. When the galactosyl acceptor is water, a galactose molecule is produced and the hydrolysis of lactose occurs. However, this transfer can be performed onto other acceptors such as sugars, yielding oligosaccharides through a transglycosylation mechanism [5]. Hydrogels are 3D networks capable of
Synthesis of divalent ligands of β-thio- and β-N-galactopyranosides and related lactosides and their evaluation as substrates and inhibitors of Trypanosoma cruzi trans-sialidase
Beilstein J. Org. Chem. 2014, 10, 3073–3086, doi:10.3762/bjoc.10.324
- inhibitors of the enzyme [19]. Also, the synthesis of the mucin oligosaccharides allowed the study of their acceptor and inhibitory properties [20][21]. Lactose derivatives were shown to be good inhibitors of the transfer of sialic acid to the natural acceptor, N-acetyllactosamine (LN) [22]. In particular
- -lactosyl residues showed to have trypanocidal activity [29]. On the other hand, a recent paper described the synthesis of 1,6-linked cyclic pseudo-galacto oligosaccharides and their in vitro sialylation by recombinant TcTS [30]. Conjugation of lactose analogs with multiarm poly(ethylene glycol) increases
Synthetic strategies for the fluorescent labeling of epichlorohydrin-branched cyclodextrin polymers
Beilstein J. Org. Chem. 2014, 10, 3007–3018, doi:10.3762/bjoc.10.319
- Cyclodextrins (CDs) are cyclic oligosaccharides consisting of 6, 7 or 8 glucopyranose units (α-, β- or γ-CD, respectively). The capability for complexation, as well as their ability to stabilize and solubilize guest compounds, makes these substances prime candidates for incorporation in delivery systems for
Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer
Beilstein J. Org. Chem. 2014, 10, 2874–2885, doi:10.3762/bjoc.10.304
- ; switchable binding behavior; Introduction α-, β- or γ-Cyclodextrins (CDs) are cyclic oligosaccharides composed of 6, 7 or 8 α-D-1,4 glucopyranose moieties, respectively. They are natural compounds produced from starch by the reaction of 4-α-glucanotransferases [1]. Their toroidal shape, with C6-primary
Thermal and oxidative stability of the Ocimum basilicum L. essential oil/β-cyclodextrin supramolecular system
Beilstein J. Org. Chem. 2014, 10, 2809–2820, doi:10.3762/bjoc.10.298
- compounds. One of the most frequently used matrices for molecular encapsulation, protection against oxidation or other degradation processes, as well as controlled release of relatively small bioactive compounds, are cyclodextrins (CDs) [30][31][32][33][34][35]. These are cyclic oligosaccharides consisting
Preparation and evaluation of cyclodextrin polypseudorotaxane with PEGylated liposome as a sustained release drug carrier
Beilstein J. Org. Chem. 2014, 10, 2756–2764, doi:10.3762/bjoc.10.292
- products. Keywords: cyclodextrins; doxorubicin; PEGylated liposome; polypseudorotaxane; sustained release; Introduction Cyclodextrins (CDs) are cyclic oligosaccharides comprising six (α-CD), seven (β-CD), and eight (γ-CD) glucopyranose units. They are characterized by a hydrophobic central cavity and a
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