A5085710385- Glycosylation and Glycoproteins Research
- Carbohydrate Chemistry and Synthesis
- Fluorine in Organic Chemistry
- Galectins and Cancer Biology
- Peptidase Inhibition and Analysis
- Microbial Metabolites in Food Biotechnology
- Sulfur-Based Synthesis Techniques
- Radical Photochemical Reactions
- Oxidative Organic Chemistry Reactions
- Polyamine Metabolism and Applications
- Enzyme function and inhibition
- Signaling Pathways in Disease
- Monoclonal and Polyclonal Antibodies Research
- Ferrocene Chemistry and Applications
- Click Chemistry and Applications
- Diet and metabolism studies
- Chemical Synthesis and Analysis
- Metabolism and Genetic Disorders
- Diet, Metabolism, and Disease
Czech Academy of Sciences, Institute of Chemical Process Fundamentals
2019-2024
University of Chemistry and Technology, Prague
2017-2024
Acylated N ‐acetyl hexosamine hemiacetals are known for their cytotoxicity. We have previously reported that cytotoxicity can be increased by replacing one or more acyloxy groups with fluorine. Herein, we present the synthesis of 4,6‐difluorinated d ‐ gluco and 4‐fluorinated galacto ‐configured hexosamine‐derived glycoconjugates organoruthenium ferrocene complexes in vitro against three cancer cell lines (A2780, SK‐OV‐3, MDA‐MB‐231) noncancerous line (HEK‐293). The attachment organometallic...
Abstract Galectins are widely expressed galactose‐binding lectins implied, for example, in immune regulation, metastatic spreading, and pathogen recognition. N ‐Acetyllactosamine (Galβ1‐4GlcNAc, LacNAc) its oligomeric or glycosylated forms natural ligands of galectins. To probe substrate specificity binding mode galectins, we synthesized a complete series six mono‐deoxyfluorinated analogues LacNAc, which each hydroxyl has been selectively replaced by fluorine while the anomeric position...
This work presents a novel series of galectin inhibitors with ferrocene and ruthenium arene motifs. Diferrocene thiodigalactoside exhibited high binding affinity selectivity for human galectin-1 over galectin-3.
Control of anomeric stereoselectivity in glycosylation with deoxofluorinated glycosyl donors is critical for assembly fluorinated oligosaccharides. Here, we report the synthesis benzylated 3-fluoro and 4-fluoro analogues phenyl 1-thioglucosazide galactosazide evaluation their a series model carbohydrate acceptors using Tf2O/Ph2SO promoter system. Low-temperature NMR revealed formation covalent α-triflate both anomers oxosulfonium triflates under selected conditions. This study demonstrates...
Introducing remote <italic>O</italic>-acyl protecting groups enabled 1,2-<italic>cis</italic> stereoselective glycosylation with fluorinated glucosazide glycosyl donors.
Multiple fluorination of glycostructures has emerged as an attractive way modulating their protein affinity, metabolic stability, and lipophilicity. Here we described the synthesis a series mono-, di- trifluorinated
The Tn antigen (GalNAcα1-Thr/Ser) is abundantly expressed in many tumors but rarely found healthy tissues, which makes it an attractive epitope for antitumor immunotherapy. use of the development therapeutic vaccines hampered by its low immunogenicity, may be enhanced deoxyfluorination GalNAc moiety. Here, we report synthesis protected 3- and 4-fluoro analogues threonine-containing antigen. As stereoselective α-linked fluorinated difficult, prepared a panel C3 C4 deoxyfluorinated...
Multiple deoxyfluorination of GlcNAc/GalNAc hemiacetals generated cytotoxic compounds.
Multiple fluorination of glycostructures has emerged as an attractive way modulating their protein affinity, metabolic stability, and lipophilicity. Here we described the synthesis a series mono-, di- trifluorinated N -acetyl-D-glucosamine D-galactosamine analogs. The key intermediates were corresponding multiply fluorinated glucosazide galactosazide thiodonors prepared from deoxyfluorinated 1,6-anhydro-2-azido-β-D-hexopyranose precursors by ring-opening reaction with phenyltrimethylsilyl...