Derivatization of a bioorthogonal protected trisaccharide linker: towards multimodal tools for chemical biology
2012 (English)In: Bioconjugate chemistry, ISSN 1043-1802, E-ISSN 1520-4812, Vol. 23, no 6, 1333-1340 p.Article in journal (Refereed) Published
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 CuI-catalyzed azide-alkyne cycloaddition reaction (CuAAC) confirms the potential use of oligosaccharides as bioorthogonal linkers in chemical biology.
Place, publisher, year, edition, pages
American Chemical Society (ACS), 2012. Vol. 23, no 6, 1333-1340 p.
spacer molecule, oligosaccharide-based, cholesterol anchor, SPR, lipid rafts, click-chemistry
National CategoryNatural Sciences
IdentifiersURN: urn:nbn:se:liu:diva-76735DOI: 10.1021/bc300160aISI: 000305358700027OAI: oai:DiVA.org:liu-76735DiVA: diva2:516517