A5038128683- Click Chemistry and Applications
- Synthesis and Catalytic Reactions
- Glycosylation and Glycoproteins Research
- Crystallization and Solubility Studies
- Chemical Synthesis and Analysis
- Carbohydrate Chemistry and Synthesis
- X-ray Diffraction in Crystallography
- Fluorine in Organic Chemistry
- Sulfur-Based Synthesis Techniques
- Oxidative Organic Chemistry Reactions
- Synthesis and Biological Evaluation
- Catalytic C–H Functionalization Methods
- Synthesis and Characterization of Heterocyclic Compounds
- Chemical Synthesis and Reactions
- Monoclonal and Polyclonal Antibodies Research
- Asymmetric Synthesis and Catalysis
- Synthetic Organic Chemistry Methods
- RNA and protein synthesis mechanisms
- Pneumocystis jirovecii pneumonia detection and treatment
- Axial and Atropisomeric Chirality Synthesis
- Cyclopropane Reaction Mechanisms
- Asymmetric Hydrogenation and Catalysis
- Coordination Chemistry and Organometallics
- Amyloidosis: Diagnosis, Treatment, Outcomes
- Vanadium and Halogenation Chemistry
Scripps Research Institute
2008-2025
University of Toronto
2004-2006
Davenport University
2004
Abstract Aryl sulfonyl chlorides (e.g. Ts‐Cl) are beloved of organic chemists as the most commonly used S VI electrophiles, and parent sulfuryl chloride, O 2 Cl , has also been relied on to create sulfates sulfamides. However, desired halide substitution event is often defeated by destruction sulfur electrophile because Cl bond exceedingly sensitive reductive collapse yielding IV species − . Fortunately, use sulfur(VI) fluorides (e.g., R‐SO ‐F SO F ) leaves only pathway open. As with click...
High fidelity: 1-Iodoalkynes react rapidly and selectively with organic azides in the presence of copper(I) catalysts (see scheme; TTTA=tris((1-tert-butyl-1H-1,2,3-triazolyl)methyl)amine). The reaction is compatible many functional groups solvents, 5-iodotriazole products were usually obtained excellent yield. These can be further functionalized to give fully substituted 1,2,3-triazoles. Detailed facts importance specialist readers are published as "Supporting Information". Such documents...
Abstract Arylsulfonylchloride (z. B. Ts‐Cl) sind die am häufigsten eingesetzten S VI ‐Elektrophile in der organischen Synthesechemie, und auch Stammverbindung, das Sulfurylchlorid (O 2 Cl ), wurde zur Synthese von Sulfaten Sulfamiden genutzt. Allerdings wird gewünschte Halogenidsubstitution oftmals durch Zersetzung des Schwefelelektrophils IV ‐Spezies − verhindert, denn ‐Cl‐Bindung ist äußerst reduktionsanfällig. Mit Schwefel(VI)‐fluoriden R‐SO ‐F SO F ) verläuft Umsetzung hingegen...
Molecules that bind selectively to a given protein and then undergo rapid chemoselective reaction form covalent conjugate have utility in drug development. Herein library of 1,3,4-oxadiazoles substituted at the 2 position with an aryl sulfonyl fluoride 5 known high affinity for inner thyroxine binding subsite transthyretin (TTR) was conceived by structure-based design principles chemically synthesized. When bound site, most fluorides react rapidly chemoselectively pKa-perturbed K15 residue,...
Sauber verklebt: 1-Iodalkine reagieren schnell und selektiv mit organischen Aziden in Gegenwart von Kupfer(I)-Katalysatoren [siehe Schema; TTTA=Tris((1-tert-butyl-1H-1,2,3-triazolyl)methyl)amin]. Viele funktionelle Gruppen Lösungsmittel können verwendet werden, die 5-Iodtriazole, sehr guten Ausbeuten entstehen, lassen sich gut zu vollständig substituierten 1,2,3-Triazolen funktionalisieren.
Fluorinated glycosides are known to resist the glycosidase-catalyzed glycosidic bond cleavage; however, synthesis of such glycans, especially 3-fluoro-sialic acid (3F-Neu5Ac) containing sialosides, has been a major challenge. Though enzymatic α-2,3-linked 3F-sialosides was reported, until recently there not any effective method available for in α-2,6-linkage. In order understand biological effect modification, we report here chemical 3Fax-Neu5Ac-α2,6-Gal as building block assembly...
Complex-type N-glycans are structurally diverse molecules, responsible for many biological processes, yet the specific sequences of involved in recognition remain largely unknown. Despite recent development efficient chemoenzymatic approaches, it is still lacking a general approach to produce complex-type N-glycans. Here, we designed two common precursors equipped with orthogonal protecting groups antennary differentiation and selective glycan elongation. The N-acetyllactosamine (LacNAc)...
[reaction: see text] The synthetic utility of alpha-halohydrazones is an underexplored area due to the lack chemo- and regioselective routes towards these molecules. Herein, we describe a general method for alpha-bromohydrazone synthesis via rearrangement alpha-bromoaziridines, which can be readily prepared first time from corresponding alkenyl bromides. alpha-bromoaziridines into alpha-bromohydrazones proceeds with high yields selectivities.
A new method for the synthesis of dihydroimidazo[1,2-a][1,3,5]triazin-4(6H)-ones via copper(I)-catalyzed hydroamination was developed. In addition, first time, iodoalkynes were shown to participate in intramolecular reaction with exclusive formation E-isomers.
The recent development of a cell culture model hepatitis C virus (HCV) infection based on the JFH-1 molecular clone has enabled discovery new antiviral agents. Using cell-based colorimetric screening assay to interrogate 1,200-compound chemical library for anti-HCV activity, we identified family 1,2-diamines derived from trans-stilbene oxide that prevent HCV at nontoxic, low micromolar concentrations in culture. Structure-activity relationship analysis ~ 300 derivatives synthesized using...
Antiviral drug resistance in influenza infections has been a major threat to public health. To develop broad-spectrum inhibitor of combat the problem resistance, we previously identified highly conserved E339...R416 salt bridge nucleoprotein trimer as target and compound 1 an disrupting with EC50 = 2.7 μM against A (A/WSN/1933). We have further modified this via structure-based approach performed antiviral activity screening identify compounds 29 30 values 110 120 nM, respectively, without...
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at glance that was extracted from about 100 leading journals. To access of an article which published elsewhere, please select “Full Text” option. The original trackable via the “References”
A variety of olefins were found to react with sulfinyl amides in the presence POCl(3) give beta-chlorosulfides and beta-hydroxysulfides good yields. In absence nucleophiles, p-tolylsulfinyl formation allylsulfoxides.
Described here is the asymmetric synthesis of iminosugar 2b, a Lipid II analog, designed to mimic transition state transglycosylation catalyzed by bacterial transglycosylase. The high density functional groups, together with rich stereochemistry, represents an extraordinary challenge for chemical synthesis. key 2,6-anti- stereochemistry ring was established through iridium-catalyzed allylic amination. developed synthetic route suitable focused libraries enable structure–activity relationship...
Phenyliodine(III) diacetate (PIDA) was found to promote facile nitrene transfer olefins and sulfoxides giving aziridines sulfoximines, respectively, in high isolated yields with selectivities.The reactions are tolerant for a range of functional groups proceed under mild conditions.The feasibility scale-up has been demonstrated.
First generation dendrimers having a high level of size/shape/symmetry homogeneity were fabricated using synthetic scheme that employs highly quantitative copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions in combination with molecular architecture favors homogeneity. An "outside-in" or convergent approach was employed wherein dendrons Sierpinski triangular fractal architectures coupled to core structures D<sub>2h</sub> D<sub>3h</sub> point group symmetries form the desired...
Novel ligands have been synthesized by the reaction of readily available aziridines with appropriate nitrogen based nucleophiles under mild conditions. Complexes different stoichiometry can be obtained upon between these and corresponding copper salts. The enantiomerically pure form one was applied in styrene cyclopropanation reaction, where catalyst revealed unexpectedly high diastereoselectivity comparison known systems.Key words: ligands, aziridines, cyclopropanation, catalysts, metal complexes.
Abstract The advances of chemical biology have provided means for a better understanding complex biological systems at the molecular level as well solutions to problems associated with systems. interdisciplinary approach was also embraced by research in glycoscience illustrated this essay some relevant examples from our group.