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Derivatization of a...
Derivatization of a bioorthogonal protected trisaccharide linker : towards multimodal tools for chemical biology
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- Fyrner, Timmy (author)
- Linköpings universitet,Organisk Kemi,Tekniska fakulteten
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- Magnusson, Karin (author)
- Linköpings universitet,Organisk Kemi,Tekniska fakulteten
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- Nilsson, Peter (author)
- Linköpings universitet,Organisk Kemi,Tekniska högskolan
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- Hammarström, Per (author)
- Linköpings universitet,Biokemi,Tekniska högskolan
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- Aili, Daniel (author)
- Linköpings universitet,Sensorvetenskap och Molekylfysik,Tekniska högskolan
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- Konradsson, Peter (author)
- Linköpings universitet,Organisk Kemi,Tekniska högskolan
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(creator_code:org_t)
- 2012-06-05
- 2012
- English.
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In: Bioconjugate chemistry. - : American Chemical Society (ACS). - 1043-1802 .- 1520-4812. ; 23:6, s. 1333-1340
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- 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.
Keyword
- spacer molecule
- oligosaccharide-based
- cholesterol anchor
- SPR
- lipid rafts
- click-chemistry
Publication and Content Type
- ref (subject category)
- art (subject category)
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