A5078475271- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Carbohydrate Chemistry and Synthesis
- Crystallography and molecular interactions
- Glycosylation and Glycoproteins Research
- Chemical Synthesis and Analysis
- Click Chemistry and Applications
- Chemical Synthesis and Reactions
- Galectins and Cancer Biology
- Microbial Natural Products and Biosynthesis
- Synthesis of Organic Compounds
- Synthesis and Catalytic Reactions
- Alkaloids: synthesis and pharmacology
- RNA and protein synthesis mechanisms
- Blood Coagulation and Thrombosis Mechanisms
- Asymmetric Synthesis and Catalysis
- Inorganic Chemistry and Materials
- Vanadium and Halogenation Chemistry
- Cancer therapeutics and mechanisms
- Studies on Chitinases and Chitosanases
- Synthesis of Indole Derivatives
- Inorganic Fluorides and Related Compounds
- Protein Tyrosine Phosphatases
- Dendrimers and Hyperbranched Polymers
- Crystal Structures and Properties
Simon Fraser University
2013-2021
École Polytechnique Fédérale de Lausanne
2019
University of Toronto
2017
Université du Québec à Montréal
2011-2013
The modular synthesis of 7 libraries containing 51 self-assembling amphiphilic Janus dendrimers with the monosaccharides d-mannose and d-galactose disaccharide d-lactose in their hydrophilic part is reported. These unprecedented sugar-containing are named glycodendrimers. Their self-assembly by simple injection THF or ethanol solution into water buffer hydration was analyzed a combination methods including dynamic light scattering, confocal microscopy, cryogenic transmission electron Fourier...
A tandem, proline-catalyzed α-chlorination/aldol reaction is described that involves a dynamic kinetic resolution of α-chloroaldehyde intermediates. The resulting syn-chlorohydrins are produced with good to excellent diastereoselectivity in high enantiopurity and provide new opportunities for the synthesis carbohydrates.
Abstract Iminosugars have attracted increasing attention as chemical probes, chaperones and leads for drug discovery. Despite several clinical successes, their de novo synthesis remains a significant challenge that also limits integration with modern high-throughput screening technologies. Herein, we describe unique synthetic strategy converts wide range of acetaldehyde derivatives into iminosugars imino- C -nucleoside analogues in two or three straightforward transformations. We show this...
Medium-sized rings, particularly the corresponding cyclic peptides, are challenging synthetic targets. In present study, we report an approach to medium-sized peptides through targeted formation and collapse of cyclol intermediates. This methodology operates on β-amino imides derived from 2,5-diketopiperazines offers a straightforward transition frequently examined scaffolds in drug discovery rarely visited class rings.
Abstract Pyrrolidine‐based iminocyclitols are a promising class of glycosidase inhibitors. Reported herein is convenient epimerization strategy that provides direct access to range stereoisomeric iminocyclitol inhibitors O‐GlcNAcase (OGA), the enzyme responsible for catalyzing removal O‐GlcNAc from nucleocytoplasmic proteins. Structural details regarding binding these bacterial homologue OGA reveal basis potency. These compounds orally available and permeate into rodent brain increase...
An efficient cyclization reaction allows for screening of large macrocycle libraries and yields a potent thrombin inhibitor.
Glycomimetics are structural mimics of naturally occurring carbohydrates and represent important therapeutic leads in several disease treatments. However, the stereochemical complexity inherent to glycomimetics often challenges medicinal chemistry efforts is incompatible with diversity-oriented synthesis approaches. Here, we describe a one-pot proline-catalyzed aldehyde α-functionalization/aldol reaction that produces an array stereochemically well-defined glycomimetic building blocks...
Abstract DNA‐encoded chemical library technologies enable the screening of large combinatorial libraries chemically and structurally diverse molecules, including short cyclic peptides. A challenge in synthesis peptides is final step, cyclization linear that typically suffers from incomplete reactions variability between substrates. Several efficient peptide strategies rely on modification thiol groups, such as formation disulfide or thioether bonds cysteines. In this work, we established a...
Abstract Our recent description of pulse sequences for the intramolecular relay 1 H polarization to 19 F reporter a carbohydrate ligand after saturation transfer from cognate lectin prompted us test applicability this technique inhibitor screening. By strategically combining synthetic organic chemistry and cell assays with F‐NMR‐based competition experiments, we document validity approach. Two mannose‐specific leguminous agglutinins as receptors, α‐methyl derivative 2‐deoxy‐2‐fluoro‐ D...
A catalytic synthesis of novel biaryl-linked divalent glycosides was achieved using an electroreductive palladium-catalyzed iodoaryl–iodoaryl coupling reaction. This new method optimized for the mannopyranosides that subsequently generalized toward several carbohydrate substrates with yields up to 96%.
Abstract Pyrrolidine‐based iminocyclitols are a promising class of glycosidase inhibitors. Reported herein is convenient epimerization strategy that provides direct access to range stereoisomeric iminocyclitol inhibitors O‐GlcNAcase (OGA), the enzyme responsible for catalyzing removal O‐GlcNAc from nucleocytoplasmic proteins. Structural details regarding binding these bacterial homologue OGA reveal basis potency. These compounds orally available and permeate into rodent brain increase...
A concise synthesis of an iminosugar from oxazole is presented that involves interrupted inverse electron-demand Kondrat’eva reaction.
Abstract A convenient one‐pot procedure is developed for the conversion of substrate (I) into iminosugar (III).