Click Multivalent Glycomaterials: Glycoclusters, Glycodendrimers, Glycopolymers, Hybrid Glycomaterials, and Glycosurfaces

Méndez‐Ardoy, Alejandro; Fernández, José Manuel Garcı́a

doi:10.1002/9781118526996.ch6

Cited by 2 publications

(1 citation statement)

References 184 publications

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“…Recent contributions by Seeberger, Yin and coworkers focus on the optimization of amphiphilic mannosylated βCD derivatives in terms of self-assembling properties and stability of the resulting mannose-functionalized nanoparticles [ 55 ]. The authors encountered that installation of seven mannosyl residues at the primary rim through copper(II)-catalyzed azide-alkyne cycloaddition (CuAAC) “click” coupling [ 56 ] and propanoyl ester groups at the fourteen secondary hydroxyls afforded conjugates (C 3 -CD-Man 7 ) that self-assembled in water. In this manner, they obtained spherical nanoparticles with an average diameter of 45 nm (TEM), an average hydrodynamic diameter of 112 nm (DLS), low polydispersity index (PDI, 0.109) and high stability under physiological conditions.…”

Section: Amphiphilicity As An Action Principle For Glycocd Self-asmentioning

confidence: 99%

Cyclodextrin-Based Functional Glyconanomaterials

2020

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Cyclodextrins (CDs) have long occupied a prominent position in most pharmaceutical laboratories as “off-the-shelve” tools to manipulate the pharmacokinetics of a broad range of active principles, due to their unique combination of biocompatibility and inclusion abilities. The development of precision chemical methods for their selective functionalization, in combination with “click” multiconjugation procedures, have further leveraged the nanoscaffold nature of these oligosaccharides, creating a direct link between the glyco and the nano worlds. CDs have greatly contributed to understand and exploit the interactions between multivalent glycodisplays and carbohydrate-binding proteins (lectins) and to improve the drug-loading and functional properties of nanomaterials through host–guest strategies. The whole range of capabilities can be enabled through self-assembly, template-assisted assembly or covalent connection of CD/glycan building blocks. This review discusses the advancements made in this field during the last decade and the amazing variety of functional glyconanomaterials empowered by the versatility of the CD component.

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Section: Amphiphilicity As An Action Principle For Glycocd Self-asmentioning

confidence: 99%

Cyclodextrin-Based Functional Glyconanomaterials

2020

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Multivalent sialylation of β-thio-glycoclusters by Trypanosoma cruzi trans sialidase and analysis by high performance anion exchange chromatography

et al. 2016

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The synthesis of multivalent sialylated glycoclusters is herein addressed by a chemoenzymatic approach using the trans-sialidase of Trypanosoma cruzi (TcTS). Multivalent β-thio-galactopyranosides and β-thio-lactosides were used as acceptor substrates and 3'-sialyllactose as the sialic acid donor. High performance anion exchange chromatography with pulsed amperometric detection (HPAEC-PAD) was shown to be an excellent technique for the analysis of the reaction products. Different eluting conditions were optimized to allow the simultaneous resolution of the sialylated species, as well as their neutral precursors. The TcTS efficiently transferred sialyl residues to di, tri, tetra and octa β-thiogalactosides. In the case of an octavalent thiolactoside, up to six polysialylated compounds could be resolved. Preparative sialylation reactions were performed using the tetravalent and octavalent acceptor substrates. The main sialylated derivatives could be unequivocally assigned by MALDI mass spectrometry. Inhibition of the transfer to the natural substrate, N-acetyllactosamine, was also studied. The octalactoside caused 82 % inhibition of sialic acid transfer when we used equimolar concentrations of donor, acceptor and inhibitor.

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Click Multivalent Glycomaterials: Glycoclusters, Glycodendrimers, Glycopolymers, Hybrid Glycomaterials, and Glycosurfaces

Cited by 2 publications

References 184 publications

Cyclodextrin-Based Functional Glyconanomaterials

Cyclodextrin-Based Functional Glyconanomaterials

Multivalent sialylation of β-thio-glycoclusters by Trypanosoma cruzi trans sialidase and analysis by high performance anion exchange chromatography

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