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Artículo
Stereoselective Synthesis of Iminosugar 2-Deoxy(thio)glycosides from Bicyclic Iminoglycal Carbamates Promoted by Cerium(IV) Ammonium Nitrate and Cooperative Brønsted Acid-Type Organocatalysis
(American Chemical Society, 2020)
The first examples of iminosugar-type 2-deoxy(thio)glycoside mimetics are reported. The key step is the activation of a bicyclic iminoglycal carbamate to generate a highly reactive acyliminium cation. Cerium(IV) ammonium ...
Artículo
sp2-Iminosugar Glycolipids as Inhibitors of Lipopolysaccharide-mediated Human Dendritic Cell Activation in Vitro and of Acute Inflammation in Mice in Vivo
(Elsevier, 219)
Glycolipid mimetics consisting of a bicyclic polyhydroxypiperidine-cyclic carbamate core and a pseudoanomeric hydrophobic tail, termed sp2-iminosugar glycolipids (sp2-IGLs), target microglia during neuroinflammatory ...
Artículo
Cyclodextrin- and calixarene-based polycationic amphiphiles as gene delivery systems: A structure-activity relationship study
(Royal Society of Chemistry, 2015)
Multi-head/multi-tail facial amphiphiles built on cyclodextrin (CD) and calixarene (CA) scaffolds are paradigmatic examples of monodisperse gene delivery systems. The possibility to precisely control the architectural ...
Artículo
Synthesis, conformational analysis and: In vivo assays of an anti-cancer vaccine that features an unnatural antigen based on an sp2-iminosugar fragment
(Royal Society of Chemistry, 2020)
The Tn antigen (GalNAc-α-1-O-Thr/Ser) is a well-known tumor-associated carbohydrate determinant. The use of glycopeptides that incorporate this structure has become a significant and promising niche of research owing to ...
Artículo
Glycomimetic-based pharmacological chaperones for lysosomal storage disorders: lessons from Gaucher, GM1-gangliosidosis and Fabry diseases
(Royal Society of Chemistry, 2016)
Lysosomal storage disorders (LSDs) are often caused by mutations that destabilize native folding and impair the trafficking of enzymes, leading to premature endoplasmic reticulum (ER)-associated degradation, deficiencies ...
Artículo
Efficient stereoselective synthesis of 2-acetamido-1,2-dideoxyallonojirimycin (DAJNAc) and sp2-iminosugar conjugates: Novel hexosaminidase inhibitors with discrimination capabilities between the mature and precursor forms of the enzyme
(Elsevier, 2016)
Due to their capacity to inhibit hexosaminidases, 2-acetamido-1,2-dideoxy-iminosugars have been widely studied as potential therapeutic agents for various diseases. An efficient stereoselective synthesis of 2-acetamido-1 ...
Artículo
Carbon Dioxide as a Traceless Caramelization Promotor: Preparation of Prebiotic Difructose Dianhydrides (DFAs)-Enriched Caramels from D-Fructose
(American Chemical Society, 2017)
Activation of a concentrated solution of D-fructose with carbonic acid, generated from carbon dioxide, induces the formation of difructose dianhydrides (DFAs) and their glycosylated derivatives (glycosyl-DFAs), a family ...
Artículo
Understanding multivalent effects in glycosidase inhibition using C-glycoside click clusters as molecular probes
(Royal Society of Chemistry, 2016)
The synthesis of the first examples of multivalent C-glycosides based on C60-fullerene or β-cyclodextrin cores by way of Cu(I)-catalyzed azide–alkyne cycloadditions is reported. These compounds were designed as molecular ...
Artículo
Multiply–linked cyclodextrin–aromatic hybrids: Caps, hinges and clips
(Taylor & Francis, 2019)
The judicious combination of shaping and recognition elements in cage-type architectures represents a powerful strategy to access molecular devices with tailored receptor properties and controlled abilities to form ...
Artículo
Pharmacological Chaperones for the Treatment of α-Mannosidosis
(American Chemical Society, 2019)
α-Mannosidosis (AM) results from deficient lysosomal α-mannosidase (LAMAN) activity and subsequent substrate accumulation in the lysosome, leading to severe pathology. Many of the AM-causative mutations compromise enzyme ...