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Search for "glycocluster" in Full Text gives 12 result(s) in Beilstein Journal of Organic Chemistry.
Orthogonal photoswitching of heterobivalent azobenzene glycoclusters: the effect of glycoligand orientation in bacterial adhesion
Beilstein J. Org. Chem. 2025, 21, 736–748, doi:10.3762/bjoc.21.57
- space and additionally, secondary interactions exerted by multivalent glycoligands have an effect on affinity. A recently introduced orthogonally photoswitchable heterobivalent azobenzene Glc/Man glycocluster was utilized to examine these aspects of carbohydrate recognition in a bacterial adhesion
- –inhibition assay. The measured results were systematically contextualized employing new reference compounds such as the respective homobivalent Man/Man glycocluster. An in-depth study comprising the analysis of the photochromic properties and the potential as inhibitors of bacterial adhesion of the synthetic
- examine the relevance of spatial glycoligand orientation. In order to expand the potential of photoswitchable glycoconjugates, we have recently introduced the first example of an orthogonally photoswitchable glycocluster in which an azobenzene α-ᴅ-mannoside and an azobenzene β-ᴅ-glucoside unit are
Carbohydrate inhibitors of cholera toxin
Beilstein J. Org. Chem. 2018, 14, 484–498, doi:10.3762/bjoc.14.34
- an IC50 value of 450 pM [63]. In another report Siegel and co-workers showed that corannulene-based pentavalent glycocluster 32 (Figure 13) bearing GM1os moieties possessed affinity for CT in low nanomolar range [64]. The IC50 value obtained was in the range of 5–25 nM. Fu et al. also synthesised and
Probing multivalency in ligand–receptor-mediated adhesion of soft, biomimetic interfaces
Beilstein J. Org. Chem. 2015, 11, 720–729, doi:10.3762/bjoc.11.82
- ligands are typically oligomers consisting of multiple subunits of varying complexity. When binding to receptors this leads to a receptor clustering or so-called glycocluster effect. However, multivalency even goes further: For example when cells form contact layers of surface anchored carbohydrates the
Synthesis of carbohydrate-scaffolded thymine glycoconjugates to organize multivalency
Beilstein J. Org. Chem. 2015, 11, 668–674, doi:10.3762/bjoc.11.75
- protecting group was observed whereas the Boc-protection remained untouched. Thus, the title glycocluster 13 was obtained in a single deprotection step. The new divalent glycoconjugate 13 shows good water solubility and is thus suited for biological testing. For photodimerization of 13, it was irradiated for
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
- equimolar concentration). The usefulness of the enzymatic trans-sialylation for the preparation of sialylated ligands was assessed by performing a preparative sialylation of a divalent substrate, which afforded the monosialylated compound as main product, together with the disialylated glycocluster
Expeditive synthesis of trithiotriazine-cored glycoclusters and inhibition of Pseudomonas aeruginosa biofilm formation
Beilstein J. Org. Chem. 2014, 10, 1981–1990, doi:10.3762/bjoc.10.206
- good affinity for Pseudomonas aeruginosa lectin lecA. They are convenient biological probes for investigating the roles of lecA and lecB in biofilm formation. Keywords: antibiotic; biofilm; glycocluster; lectin; multivalency effect; multivalent glycosystems; Introduction Pseudomonas aeruginosa (PA
- is often based on the recognition of multiple epitopes through a synergistic and cooperative effect, called the ‘’glycocluster effect” [14][15][16]. It has been shown in a number of systems that multivalency effects can be exploited to obtain high-avidity synthetic ligands against various types of
- dimethyldioxirane (DMDO) generated in situ in the presence of a phase-transfer catalyst, followed by treatment with NaN3 [39]. This afforded the silyl-protected D-galactose trithiotriazine–triazole glycocluster 11 under CuSO4/sodium ascorbate-catalyzed cycloaddition conditions [40] (20 °C, 24 h), in a satisfactory
Clicked and long spaced galactosyl- and lactosylcalix[4]arenes: new multivalent galectin-3 ligands
Beilstein J. Org. Chem. 2014, 10, 1672–1680, doi:10.3762/bjoc.10.175
- between the tetraalkyne calix[4]arene 8 and azido-galactoside 5 to give glycocluster 9 (83% yield) was carried out in DMF and H2O with CuSO4 and sodium ascorbate following a microwave-assisted procedure (20 min, 150 W, 80 °C). No partially functionalized compounds or other byproducts were detected in the
Photoswitchable precision glycooligomers and their lectin binding
Beilstein J. Org. Chem. 2014, 10, 1603–1612, doi:10.3762/bjoc.10.166
- affinity carbohydrate ligands by displaying several monosaccharides/oligosaccharides on a protein scaffold or through a patch of lipids. This is known as the glycocluster effect or the multivalent presentation of sugar ligands [3][4]. This strategy can also be employed for the synthesis of carbohydrate
Synthesis and solvodynamic diameter measurements of closely related mannodendrimers for the study of multivalent carbohydrate–protein interactions
Beilstein J. Org. Chem. 2014, 10, 1524–1535, doi:10.3762/bjoc.10.157
- :0 to 90:10) afforded the desired glycocluster. Procedure B: Zemplén de-O-acetylation procedure for insoluble hydroxylated derivatives The acetylated compound was dissolved in anhydrous MeOH and a solution of sodium methoxide (1 M in MeOH, 5 µL every 20 min until precipitation) was added. An
- yield the fully deprotected glycocluster. Synthesis of peracetylated trivalent derivative 8: To a solution of triazido core 6 (50.0 mg, 109 μmol, 1.00 equiv) and mannoside 7 (158 mg, 409 μmol, 3.75 equiv) in a THF/H2O mixture (1:1, 6 mL) were added sodium ascorbate (19.4 mg, 98.1 μmol, 0.90 equiv) and
Bis(β-lactosyl)-[60]fullerene as novel class of glycolipids useful for the detection and the decontamination of biological toxins of the Ricinus communis family
Beilstein J. Org. Chem. 2014, 10, 1504–1512, doi:10.3762/bjoc.10.155
- interest [7][8]. In particular, multivalent biomaterials carrying more than two carbohydrate ligands have been designed [9][10][11][12][13][14][15] and proven to enhance protein–carbohydrate interactions by means of glycocluster effects [16][17][18]. More recently, our research group has reported on
High-affinity multivalent wheat germ agglutinin ligands by one-pot click reaction
Beilstein J. Org. Chem. 2012, 8, 819–826, doi:10.3762/bjoc.8.91
- sample of disaccharide 1 was eluted from a silica gel column for a second time. In comparison, the use of the less polar propargyl β-D-glucoside instead of 1 in the one-pot procedure with amine A4 led to the corresponding divalent glycocluster in a yield of 86% [48]. Finally, O-deacetylation of the
- divalent ligand C4 with its two chitobiose moieties occupying two adjacent binding sites of WGA. The linker is conformationally largely unrestricted and can adopt several low-energy conformations. WGA chain 1 is colored yellow, chain 2 is blue. Synthesis of glycocluster B5 with isolation of the
Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations
Beilstein J. Org. Chem. 2012, 8, 421–427, doi:10.3762/bjoc.8.47
- observed that a tetravalent glycocluster can be obtained in good yields and as a unique 1,4-regioisomer by using a catalytic amount of copper micropowder in a mixture of isopropanol and ammonium acetate buffer [42]. Therefore we decided to follow similar conditions in this study with propargyl glycosides
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