Click Multivalent Heterogeneous Neoglycoconjugates – Modular Synthesis and Evaluation of Their Binding Affinities

Ortega‐Muñoz, Mariano; Perez‐Balderas, Francisco; Morales‐Sanfrutos, Julia; Hernández-Matéo, Fernando; Isac‐García, Joaquín; Santoyo‐González, Francisco

doi:10.1002/ejoc.200801169

Cited by 59 publications

(40 citation statements)

References 89 publications

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“…The Dowex M-4195 resin was purchased from Supelco and subjected to a conditioning treatment. The vinyl sulfone propyl silica gel 5, [28] the aminopropyl silica gel 6, [29] the alkynes 10, [38] 15, [39] 16, [40] 17, [41] 18 [42] and 19, [43] the azides 21, [44] 22, [45] 23, [46] 24, [47] 25, [48] 27, [49] and 28 [50] and the alkyne and azido functionalized silicas [33] used as click scavengers were prepared according to reported procedures in literature. TLCs were performed on Merck Silica Gel 60 F 254 aluminium sheets.…”

Section: Experimental Section Generalmentioning

confidence: 99%

Non‐Magnetic and Magnetic Supported Copper(I) Chelating Adsorbents as Efficient Heterogeneous Catalysts and Copper Scavengers for Click Chemistry

et al. 2010

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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 and silica-coated magnetite nanoparticles as suitable supports and the aza-Michael-type addition of vinyl sulfones as the ligation tool. These adsorbents are versatile materials with applications in the copper-catalyzed alkyne-azide cycloaddition (CuAAC) click chemistry where their complexation abilities enable them to act either as heterogeneous click catalysts when used in their complexed form or as copper(I) scavengers when used in their uncomplexed form. In the first instance, they proved to be robust and efficient heterogeneous catalysts to promote click reactions using extremely low doses and showing negligible copper leaching, particularly in the case of the silica-based non-magnetic adsorbents, allowing a simple operational protocol for their rapid and easy removal by filtration or magnetic decantation and showing good recyclability properties. In their uncomplexed form, the non-magnetic chelating adsorbents are very efficient copper scavengers that are able to remove any traces of metal contamination and that can be applied in tandem with any heterogeneous supported copper(I) catalysts or as standalone copper removing system in any click protocol allowing the isolation of metal-free clicked compounds.

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Section: Experimental Section Generalmentioning

confidence: 99%

Non‐Magnetic and Magnetic Supported Copper(I) Chelating Adsorbents as Efficient Heterogeneous Catalysts and Copper Scavengers for Click Chemistry

et al. 2010

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“…A few other studies have also reported that lectin binding to glycan mixtures is stronger than the binding to a single glycan. [8–11] However, the mechanism of such hetero-multivalency is not clear.…”

Section: Introductionmentioning

confidence: 99%

Hetero-multivalent binding of cholera toxin subunit B with glycolipid mixtures

Krishnan

Singla

Lee

et al. 2017

Colloids and Surfaces B: Biointerfaces

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GM1 has generally been considered as the major receptor that binds to cholera toxin subunit B (CTB) due to its low dissociation constant. However, using a unique nanocube sensor technology, we have shown that CTB can also bind to other glycolipid receptors, fucosyl-GM1 and GD1b. Additionally, we have demonstrated that GM2 can contribute to CTB binding if present in a glycolipid mixture with a strongly binding receptor (GM1/fucosyl-GM1/GD1b). This hetero-multivalent binding result was unintuitive because the interaction between CTB and pure GM2 is negligible. We hypothesized that the reduced dimensionality of CTB-GM2 binding events is a major cause of the observed CTB binding enhancement. Once CTB has attached to a strong receptor, subsequent binding events are confined to a 2D membrane surface. Therefore, even a weak GM2 receptor could now participate in second or higher binding events because its surface reaction rate can be up to 104 times higher than the bulk reaction rate. To test this hypothesis, we altered the surface reaction rate by modulating the fluidity and heterogeneity of the model membrane. Decreasing membrane fluidity reduced the binding cooperativity between GM2 and a strong receptor. Our findings indicated a new protein-receptor binding assay, that can mimic complex cell membrane environment more accurately, is required to explore the inherent hetero-multivalency of the cell membrane. We have thus developed a new membrane perturbation protocol to efficiently screen receptor candidates involved in hetero-multivalent protein binding.

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“…However, recent studies suggested that the combination of different binding or non-binding sugars and their simultaneous multivalent presentation on a single scaffold can influence the resulting binding properties in both affinity and selectivity e.g. towards a specific protein receptor (49,50). Thus it would be highly relevant to obtain and study sequence-defined heteromultivalent glycomacromolecules presenting different sugar ligands at defined positions along the scaffold.…”

Section: Monodisperse Sequence-defined Glycomacromolecules Via Solidmentioning

confidence: 99%

Recent Advances in Solid Phase Polymer Synthesis: Polyamides from Tailor-Made Building Blocks

Wojcik

Ponader

Mosca

et al. 2014

ACS Symposium Series

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Click Multivalent Heterogeneous Neoglycoconjugates – Modular Synthesis and Evaluation of Their Binding Affinities

Cited by 59 publications

References 89 publications

Non‐Magnetic and Magnetic Supported Copper(I) Chelating Adsorbents as Efficient Heterogeneous Catalysts and Copper Scavengers for Click Chemistry

Non‐Magnetic and Magnetic Supported Copper(I) Chelating Adsorbents as Efficient Heterogeneous Catalysts and Copper Scavengers for Click Chemistry

Hetero-multivalent binding of cholera toxin subunit B with glycolipid mixtures

Recent Advances in Solid Phase Polymer Synthesis: Polyamides from Tailor-Made Building Blocks

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