Derivatization of a bioorthogonal protected trisaccharide linker-toward multimodal tools for chemical biology

Bioconjugate Chemistry
Timmy FyrnerPeter Konradsson

Abstract

When cross-linking biomolecules to surfaces or to other biomolecules, the use of appropriate spacer molecules is of great importance. Mimicking the naturally occurring spacer molecules will give further insight into their role and function, possibly unveil important issues regarding the importance of the specificity of carbohydrate-based anchor moieties, in e.g., glycoproteins and glycosylphosphatidylinositols. Herein, we present the synthesis of a lactoside-based trisaccharide, potentially suitable as a heterobifunctional bioorthogonal linker molecule whereon valuable chemical handles have been conjugated. An amino-derivative having thiol functionality shows promise as novel SPR-surfaces. Furthermore, the trisaccharide has been conjugated to a cholesterol moiety in combination with a fluorophore which successfully assemble on the cell surface in lipid microdomains, possibly lipid-rafts. Finally, a Cu(I)-catalyzed azide-alkyne cycloaddition reaction (CuAAC) confirms the potential use of oligosaccharides as bioorthogonal linkers in chemical biology.

References

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Citations

Jan 23, 2016·Chemical Reviews·Vinod K TiwariXi Chen
Feb 18, 2014·Bioconjugate Chemistry·Sébastien RedonStéphane Chambert
May 10, 2016·Organic & Biomolecular Chemistry·Niek N H M EisinkAdriaan J Minnaard
Jun 20, 2013·Chembiochem : a European Journal of Chemical Biology·Bridget L Stocker, Mattie S M Timmer
Jun 25, 2021·Chemical Reviews·Anand K AgrahariVinod K Tiwari
Jul 7, 2018·Chemical Reviews·Carmanah D HunterChristopher W Cairo

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