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Glycoclusters as lectin inhibitors: comparative analysis on two plant agglutinins with different folding as a step towards rules for selectivity
(Elsevier, 2015-09-23)
The emerging physiological significance of carbohydrate (glycan) protein (lectin) recognition engenders the interest to design synthetic inhibitors with a high level of selectivity among natural sugar receptors. Plant ...
Allylic azide rearrangement in tandem with Huisgen cycloaddition for stereoselective annulation: synthesis of C-Glycosyl iminosugars
(American Chemical Society, 2015-12-09)
Allylic azide rearrangement is used. in,tandem with. intramolecular azide-alkene cycloaddition to give a triazoline that when subsequently decomposed in the presence of a nucleophile gives piperidines. The tandem reaction ...
Bi- to tetravalent glycoclusters presenting GlcNAc/GalNAc as inhibitors: from plant agglutinins to human macrophage galactose-type lectin (CD301) and galectins
(Royal Society of Chemistry, 2015-02-17)
Emerging insights into the functional spectrum of tissue lectins leads to identification of new targets for the custom-made design of potent inhibitors, providing a challenge for synthetic chemistry. The affinity and ...
Coiled coil type neoglycoproteins presenting three lactose residues
(Elsevier, 2016-02-06)
Scaffold design, synthesis and application are relevant for biomedical research. For example, multivalent interactions, such as those between cell surface glycoproteins and lectins can influence the potency and duration ...
Lewis acid induced anomerization of se-glycosides. Application to synthesis of alpha-Se-GalCer
(American Chemical Society, 2016-01-22)
The TiCl4 induced anomerization of selenium glycosides of galacturonic acid derivatives is reported. The reaction was successful for galacturonic acid when various alkyl, alkenyl, alkynyl, saccharide, steroid, and lipid ...
Synthesis of iminosugar derivatives presenting naphthyl and alkyl amine interacting groups and binding to somatostatin receptors
(Royal Society of Chemistry, 2014-03-20)
The synthesis of 1-deoxynojirimycin (DNJ) derivatives presenting a 2-naphthylmethyl and an alkyl amino side chain from L-sorbose is described. The synthetic derivatives were tested for their ability to inhibit the binding ...
Synthesis of migrastatin and its macroketone analogue and in vivo FRAP analysis of the macroketone on E-Cadherin dynamics
(Wiley-VCH Verlag, 2014-06-11)
An efficient and scalable synthesis of a key acyclic intermediate used for the preparation of migrastatin and its macroketone analogue is described; Brown alkoxyallylation is the key step for this synthesis. The macroketone ...
Synthesis of α-galactosyl ceramide analogues with an α-triazole at the anomeric carbon
(Elsevier, 2014-03-16)
The synthesis of 1,2,3-triazole containing analogues of a-GalCer and galacturonic acid containing Sphingomonous cell wall antigens is described. Anomerisation was used to provide the required cc-glycosyl azide precursor. ...
Decorated macrocycles via ring-closing double-reductive amination. Identification of an apoptosis inducer of leukemic cells that at least partially antagonizes a 5-HT2 receptor
(American Chemical Society, 2015-03-16)
A build-couple-pair strategy, including double-reductive amination macrocyclization, has been used to generate decorated macrocycles (eannaphanes) with an embedded triazole and monosaccharide. Biological screening led to ...
Stereoselective epimerizations of glycosyl thiols
(American Chemical Society, 2017-10-17)
Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while ...