Expeditive Synthesis of Glycodendrimer Scaffolds Based on Versatile TRIS and Mannoside Derivatives

Chabre, Yoann M.; Contino‐Pépin, Christiane; Placide, Virginie; Shiao, Tze Chieh; Roy, René

doi:10.1021/jo8008935

Cited by 91 publications

(70 citation statements)

References 28 publications

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“…[51] The synthetic methodology started with the known 2-bromoacetamido-tris[(propargyloxy)methyl]aminomethane 44, obtained on a gram-scale in 37 % overall yield via a four-step sequence from Tris. [52] Reaction of azido Cgalactopyranoside 10 b with the tripropargylated precursor 44 under click chemistry conditions afforded the trivalent G(0)-galactodendron 45 in 90 % yield. To generate a suitable terminal functionality for subsequent attachment to polyalkynylated dendritic cores, S N 2 displacement of the bromide in 45, using sodium azide in DMF, quantitatively afforded the desired azido dendron 46 (Scheme 5).…”

Section: Resultsmentioning

confidence: 99%

Combining Glycomimetic and Multivalent Strategies toward Designing Potent Bacterial Lectin Inhibitors

Chabre

Giguère

Blanchard

et al. 2011

Chemistry A European J

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As part of ongoing activities toward the design of potent and selective ligands against galactoside-binding proteins from animal, bacterial, and plant lectins, a systematic investigation involving the synthesis and binding evaluations of a series of original β-C-galactopyranoside mimetics is described. The multivalent presentation of partly optimized candidates on various dendritic scaffolds through Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAc) has also been achieved. Biophysical investigations based on isothermal titration calorimetry (ITC) have indicated a dissociation constant in the low micromolar range for the best optimized monovalent conjugate (K(d)=37 μM). The results thus confirmed that stable C-galactosides could represent efficient synthetic glycomimetics of natural α-linked oligosaccharidic inhibitors of PA-IL lectin (Lec A) from the pathogenic Pseudomonas aeruginosa. Striking enhancements in the avidity of the glycoconjugates were also observed for tri-, hexa-, and nonavalent derivatives, among which the most potent exhibited dissociation constants below 500 nM, corresponding to a 400-fold increase in affinity compared with the β-D-Gal-O-Me used as reference. To deepen our understanding of the binding mode of the best glycomimetics involved in the recognition process, molecular modeling studies, docking calculations, and NMR diffusion measurements have been performed. Although favorable complementary interactions induced by the addition of the hydrophobic aglycon might explain the affinity enhancement, experimental determination of the size and the topology of the multivalent conjugates further supported the formation of aggregative complexes as a major multivalent binding mode. This work represents a systematic and comprehensive study towards a thorough understanding of the protein-carbohydrate interactions involved in Pseudomonas aeruginosa infection, and as such should prove useful for the development of stable and optimized anti-adhesive agents.

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Section: Resultsmentioning

confidence: 99%

Combining Glycomimetic and Multivalent Strategies toward Designing Potent Bacterial Lectin Inhibitors

Chabre

Giguère

Blanchard

et al. 2011

Chemistry A European J

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“…The simplicity of the procedure relied on the efficient of the multivalent CUAAC cycloaddition 39,40,[42][43][44] between the known glucosyl azide 1 41 and tetrapropargylated pentaerythritol 2 42 to provide peracetylated . It is worth mentioning that this type of dendrimer build-up strategy, using "glyconanosynthons" 34,38 and providing 16-surface OH functionalities at the G0 level, constitutes a distinctive advantage over other classical dendrimer syntheses using AB 2 -type scaffolds and building blocks.…”

Section: Synthesismentioning

confidence: 99%

Improved carbon dioxide storage over clay-supported perhydroxylated glucodendrimer

et al. 2017

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Low-cost biosourced hybrid microporous adsorbents with improved affinity towards carbon dioxyde (CO2) were prepared through the incorporation of various amounts of glucosylated dendrimer into bentonite- and montmorillonite-rich composite materials. Characterization by nitrogen adsorption–desorption isotherms, surface specific and pore size analyses (BET and BJH), thermogravimetric analysis (TGA), Fourier transform infrared spectroscopy (FTIR), and X-ray diffraction (XRD) revealed changes in the interlayer spacing and textural structure of the materials. Thermal programmed desorption measurements (TPD) showed significant improvements of the retention capacity of CO2 (CRC) and water (WRC). This was explained in terms of enhancement of both surface basicity and hydrophilic character due to the incorporation of terminal polyhydroxyl groups. The CRC was found to vary according to the previous saturation time with CO2 and the carrier gas throughput. CO2 was totally released upon temperature not exceeding 80 °C or even at room temperature upon strong carrier gas stream, thus providing evidence that CO2 capture involves almost exclusively physical interaction with the OH groups of the dendrimer. This result opens promising prospects for the reversible capture of carbon dioxide with easy release without thermal regeneration, more particularly when extending this concept to biosourced dendrimers.

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“…Firstly, we have prepared the hydrophobic moiety. Thus, the known 3α-N 3 -ursodeoxycholic methyl ester (3αN 3 UDC) [24] and the tris-propargyloxyamino derivative 9 obtained from TRIS according to a literature procedure [25] were chosen as building blocks for its synthesis. For assembling the desired tri-valent bile acid scaffold 10 we used the copper-catalyzed azide-alkyne cycloaddition (CuAAC) under microwave irradiations.…”

Section: Exon Skippingmentioning

confidence: 99%

Conjugated Oligonucleotides for Biochemical Applications

Capobianco¹,

Navacchia²,

Marchesi³

et al. 2017

Med chem

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In the last 30 years oligonucleotides i.e., relatively short polymers (usually 12-24 units long) based on DNA structure, have found a widespread use in biochemical studies and as biochemical probes and chemotherapeutic agents for the downregulation of genetic expression or for exon skipping. Here we present a short review of studies from our laboratories on the synthesis and applications of different kind of conjugates to address some of these techniques. Preparation of conjugates with small alkyl groups, intercalators, fluorescent oligothiophenes, and lipophilic bile-acids will be discussed.

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Expeditive Synthesis of Glycodendrimer Scaffolds Based on Versatile TRIS and Mannoside Derivatives

Abstract: A new family of glycodendrimer scaffolds containing 12 and 18 peripheral alpha-d-mannopyranosidic units has been synthesized by Cu(I)-catalyzed [1,3]-dipolar cycloadditions using sulfurated dendritic scaffolds bearing alkyne functionalities and novel TRIS derivatives.

Cited by 91 publications

References 28 publications

Combining Glycomimetic and Multivalent Strategies toward Designing Potent Bacterial Lectin Inhibitors

Combining Glycomimetic and Multivalent Strategies toward Designing Potent Bacterial Lectin Inhibitors

Improved carbon dioxide storage over clay-supported perhydroxylated glucodendrimer

Conjugated Oligonucleotides for Biochemical Applications

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