From the Ganglioside GQ1b? to Glycomimetic Antagonists of the Myelin-Associated Glycoprotein (MAG)

Ernst, Beat; Schwardt, Oliver; Mesch, Stefanie; Wittwer, Matthias; Rossato, Gianluca; Vedani, Angelo

doi:10.2533/chimia.2010.17

Chimia

2010

DOI: 10.2533/chimia.2010.17

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From the Ganglioside GQ1b? to Glycomimetic Antagonists of the Myelin-Associated Glycoprotein (MAG)

Beat Ernst

Oliver Schwardt²,

Stefanie Mesch³

et al.

Abstract: Thetetrasaccharide4,asubstructureofgangliosideGQ1bα,showsaremarkableaffinityforthemyelinassociatedglycoprotein(MAG)andwasthereforeselectedasstartingpointforaleadoptimizationprogram.Inour searchforstructurallysimplifiedandpharmacokineticallyimprovedmimicsof4,antagonistswithmodificationsof thecoredisaccharideGalb(1-3)GalNAc,aswellastheterminalα(2-3)-andtheinternalα(2-6)-linkedneuraminic acidweresynthesizedandtestedintarget-basedbindingassays.Comparedtothereferencetetrasaccharide4, themostpotentantagonist17exhibi… Show more

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Cited by 4 publications

(1 citation statement)

References 36 publications

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“…7 On the other hand, the terminal di-sialyl GNB component of gangliosides GD1α, GT1aα and GQ1bα is the minimal binding epitope of myelin-associated glycoprotein (MAG) ligands, 8 and is considered as a leading target for developing MAG inhibitors to enhance regeneration of central nervous system axons after injury in adult mammals. 9 …”

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confidence: 99%

Efficient chemoenzymatic synthesis of novel galacto-N-biose derivatives and their sialylated forms

Liu

et al. 2015

Chem. Commun.

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Galacto-N-biose (GNB) derivatives were efficiently synthesized from galactose derivatives via a one-pot two-enzyme system containing two promiscuous enzymes from Bifidobacterium infantis: a galactokinase (BiGalK) and a D-galactosyl-β1–3-N-acetyl-D-hexosamine phosphorylase (BiGalHexNAcP). Mono-sialyl and di-sialyl galacto-N-biose derivatives were then prepared using a one-pot two-enzyme system containing a CMP-sialic acid synthetase and an α2–3-sialyltransferase or an α2–6-sialyltransferase.

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confidence: 99%

Efficient chemoenzymatic synthesis of novel galacto-N-biose derivatives and their sialylated forms

Liu

et al. 2015

Chem. Commun.

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Regioselective Chemoenzymatic Synthesis of Ganglioside Disialyl Tetrasaccharide Epitopes

et al. 2014

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A novel chemoenzymatic approach for the synthesis of disialyl tetrasaccharide epitopes found as the terminal oligosaccharides of GD1α, GT1aα, and GQ1bα is described. It relies on chemical manipulation of enzymatically generated trisaccharides as conformationally constrained acceptors for regioselective enzymatic α2–6-sialylation. This strategy provides a new route for easy access to disialyl tetrasaccharide epitopes and their derivatives.

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Interfacial Tension of Methylbenzene–Water in the Presence of Hydrophilic and Hydrophobic Alumina Nanoparticles at Different Temperatures

2013

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The effect of almost low concentrations of alumina hydrophilic (bare surface) and hydrophobic (modified surface with hexadecanoic acid) nanoparticles on interfacial tension of methylbenzene (toluene)−water was investigated based on experimental results from drop weight tensiometry. Nanoparticles were suspended in either aqueous or organic phases to provide a stable nanofluid and then were contacted with another phase to measure the interfacial tension. A nanoparticle mass fraction range of 1•10 −5 to 5•10 −4 (± 5•10 −6 ) and a temperature range of [293.2 to 323.2 (± 0.1)] K were used. Interesting trends of interfacial tension variation were revealed with nanoparticles concentration, showing a sharp increase up to 55.7 mN•m −1 (± 0.1 mN•m −1 ) at 293.2 K, and a decrease to about 14.0 mN•m −1 at 323.2 K with hydrophilic and hydrophobic forms, respectively. The effect of increasing temperature was found to reduce interfacial tension within the used ranges and significantly higher with hydrophilic nanoparticles.

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From the Ganglioside GQ1b? to Glycomimetic Antagonists of the Myelin-Associated Glycoprotein (MAG)

Cited by 4 publications

References 36 publications

Efficient chemoenzymatic synthesis of novel galacto-N-biose derivatives and their sialylated forms

Efficient chemoenzymatic synthesis of novel galacto-N-biose derivatives and their sialylated forms

Regioselective Chemoenzymatic Synthesis of Ganglioside Disialyl Tetrasaccharide Epitopes

Interfacial Tension of Methylbenzene–Water in the Presence of Hydrophilic and Hydrophobic Alumina Nanoparticles at Different Temperatures

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