[reaction: see text] The construction of multivalent neoglycoconjugates is efficiently achieved by the regiospecific catalytic cycloaddition alkynes and azides using organic-soluble copper complexes (Ph(3)P)(3).CuBr (EtO)(3)P.CuI. simultaneous use microwave irradiation shortened notably reaction times.

The easy functionalization of tags and solid supports with the vinyl sulfone function is a valuable tool in omic sciences that allows their coupling amine thiol groups present proteogenic residues proteins, mild green conditions compatible biological function.

Abstract Novel supported chelating adsorbents bearing diverse multidentate nitrogenated ligands with strong copper(I) affinities are easily prepared in non‐magnetic and magnetic variants using silica silica‐coated magnetite nanoparticles as suitable supports the aza‐Michael‐type addition of vinyl sulfones ligation tool. These versatile materials applications copper‐catalyzed alkyne‐azide cycloaddition (CuAAC) click chemistry where their complexation abilities enable them to act either...

Abstract The covalent immobilization of suitable alkyne/azide carbohydrate derivatives on complementarily functionalizated azide/alkyne silica was performed by click ligation througth the Cu(I)‐catalyzed 1,3‐dipolar cycloaddition reaction such compounds. new glyco‐silicas have shown to be efficient and valuable bio‐selective affinity chromatographic supports for purification lectins as well one‐pot fluorescent labeling those proteins. synthetic methodology is simple, high yielding flexible,...

The efficient synthesis of fluorescent and non-fluorescent multivalent neoglycoconjugates is described by means the Cu(I) catalyzed azide–alkyne 1,3-dipolar cycloaddition ("click-chemistry"). A well-defined glycopolymer, glycocyclodextrin or glycocluster architecture displaying galactose lactose epitopes has been chosen. Cellular assays using U-937 RAW 264.7 monocyte/macrophage cells showed that these glycocompounds have capability to act as synthetic activators mimicking lipopolysaccharide...

ADVERTISEMENT RETURN TO ISSUEPREVNoteNEXTSynthesis of Calixarene-Based Cavitands and Nanotubes by Click ChemistryJulia Morales-Sanfrutos, Mariano Ortega-Muñoz, Javier Lopez-Jaramillo, Fernando Hernandez-Mateo, Francisco Santoyo-Gonzalez*View Author Information Instituto de Biotecnología, Departamento Química Orgánica, Facultad Ciencias, Campus Fuentenueva s/n, Universidad Granada, Granada E-18071, Spain[email protected]Cite this: J. Org. Chem. 2008, 73, 19, 7768–7771Publication Date...

Abstract The efficient synthesis of structurally diverse, multivalent, heterogeneous neoglycoconjugates by means a series different click‐based strategies is described. methodology highly and versatile allowing for easy access to mannose (α‐Man)‐containing glycoconjugates differing in their valency, nature the scaffold, constitutive sugars length linker. influence those structural parameters on binding affinities these glycomimics toward Concanavalin A (Con A) was evaluated.(© Wiley‐VCH...

The combination of silica as support and vinyl sulfone reactive group led to a pre-activated material that readily reacts form covalent bonds by Michael-type addition with both amine thiol groups naturally occurring in biomolecules mild conditions compatible the biological nature enzymes. A simple two step synthetic strategy was designed access this functionalized hybrid material. Two types silicas (N-type S-type) differing chemical linkers between particle were prepared implementation...

Amphiphilic dendrimer-based gene delivery vectors bearing peripheral alkyl sulfonyl hydrophobic tails were constructed using low-generation PAMAM-G2 as the core and functionalized by means of aza-Michael type addition its primary amino groups to vinylsulfone derivatives an efficient tool for surface engineering. While unmodified was unable efficiently transfect eukaryotic cells, dendrimers able bind DNA at low N/P ratios, protect from digestion with DNase I showed high transfection...

The aim of this study was to evaluate the crosslinking abilities divinyl sulfone (DVS) for preparation novel water-insoluble cyclodextrin-based polymers (CDPs) capable forming inclusion complexes with different guest molecules. Reaction DVS native α-cyclodextrin (α-CD), β-cyclodextrin (β-CD) and/or starch generates a variety homo- and hetero-CDPs degrees as function reactants’ stoichiometric ratio. materials were characterized by powder X-ray diffraction, electron microscopy their sorption...

The construction of multivalent structures such as sugar heterodimers, glycoclusters, calix sugars, multicalixarenes, and glycocyclodextrins is designed by using 1,3-dipolar cycloaddition a versatile efficient tool which allows the creation heterocyclic bridges between different units that are coupled.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of phenyl 2-azido-2-deoxy-1-selenoglycosides from glycalsF. Santoyo-Gonzalez, F. G. Calvo-Flores, P. Garcia-Mendoza, Hernandez-Mateo, J. Isac-Garcia, and R. Robles-DiazCite this: Org. Chem. 1993, 58, 22, 6122–6125Publication Date (Print):October 1, 1993Publication History Published online1 May 2002Published inissue 1 October 1993https://pubs.acs.org/doi/10.1021/jo00074a048https://doi.org/10.1021/jo00074a048research-articleACS...

A cyclomaltooligosaccharide containing seven α-(1→4)-d-glucopyranosyl units (β-cyclodextrins) was transformed into heptakis 6-deoxy-6-iodo (13) and 6-amino-6-deoxy (25) derivatives using known procedures. Compound 13 peracetylated condensed in one pot with the pseudothiouronium salts of β-d-glucopyranose (4), β-d-galactopyranose (5), or β-d-N-acetylglucopyranosylsamine (6) α-d-1-deoxy-1-thiomannopyranose (8) cesium carbonate dimethylformamide. Alternatively, 4-aminophenyl-α-d-mannopyranoside...

The introduction of multiple labels onto biomolecules is a challenge. We report herein the synthesis vinyl sulfone derivatized bifunctional tag single-attachment-point reagents (BTSAP) bearing biotin and fluorescent their applications in proteins for by means Michael-type addition electrophilic group. These BTSAP were easily synthesized two-step chemical strategy involving preparation alkyne tags (AVST) subsequent click CuAAC attachment second azide functionalized tag. direct coupling with...

Carbohydrate-mediated molecular recognition is involved in many biological aspects such as cellular adhesion, immune response, blood coagulation, inflammation, and infection. Considering the crucial importance of events which proteins are normally involved, synthetic saccharide-based systems have emerged powerful tools for understanding protein-carbohydrate interactions. As a new approach to create systems, set representative monosaccharides (D-mannose, D-glucose, N-acetyl-D-glucosamine,...

Gene transfection mediated by the cationic polymer polyethylenimine (PEI) is considered a standard methodology. However, while highly branched PEIs form smaller polyplexes with DNA that exhibit high efficiencies, they have significant cell toxicity. Conversely, low molecular weight (LMW-PEIs) favorable cytotoxicity profiles display minimum activities as result of inadequate complexation and protection. To solve this paradox, novel polyelectrolyte complex was prepared ionic cross-linking 1.8...

A new efficient and expeditious one-pot synthesis of thiiranes olefins from cyclic sulfates vic-diols is described. Opening with potassium thioacetate or thiocyanate followed by treatment sodium methoxide led to episulfides. Olefins were obtained when selenocyanate was used as nucleophile, the monoesters treated borohydride. This method applied acyclic polyols derived chiral glycerine, 1,2-isopropylidenehexofuranoses different subtituents at C-3, dimethyl acetals pentoses hexoses. The...

Abstract Mannose (α‐Man)‐containing neoglycoconjugates possessing aliphatic‐, aromatic‐, and carbohydrate‐centered architectures differing in structural characteristics such as valency, topology, nature of the linker have been synthesized using click chemistry that shows its value an efficient versatile methodology for accessing tailor‐made multivalent neoglycoconjugates. The binding behaviour these glycomimics toward Concanavalin A (Con A) has evaluated to determine influence parameters. (©...

Abstract

A palladium-catalyzed Sonogashira reaction has been applied for the syntheses of divalent "sugar-rods" which exhibited excellent lectin cross-linking properties. The procedure, involves a tetrakis(triphenylphosphine)palladium-catalyzed cross-coupling between an alkyne and halogen-bearing sp2-carbon in DMF at 60 degrees C, is very efficient dimeric or heterobifunctional (8-13, 15-17) were isolated 65-100% yields. Dimers 8a 15a both shown to form insoluble cross-linked lattices when mixed with...