Derivatization of a bioorthogonal protected trisaccharide linker - towards multimodal tools for chemical biology.
Summary of "Derivatization of a bioorthogonal protected trisaccharide linker - towards multimodal tools for chemical biology."
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.
Affiliation
Journal Details
This article was published in the following journal.
Name: Bioconjugate chemistry
ISSN: 1520-4812
Pages:
Links
- PubMed Source: http://www.ncbi.nlm.nih.gov/pubmed/22568531
- DOI: http://dx.doi.org/10.1021/bc300160a
Medical and Biotech [MESH] Definitions
Raffinose
A trisaccharide occurring in Australian manna (from Eucalyptus spp, Myrtaceae) and in cottonseed meal.
Drugs, Generic
Drugs whose drug name is not protected by a trademark. They may be manufactured by several companies.
Desmoplakins
Desmoplakins are cytoskeletal linker proteins that anchor INTERMEDIATE FILAMENTS to the PLASMA MEMBRANE at DESMOSOMES.
Single-chain Antibodies
A form of antibodies (scFv) consisting of the variable regions of only the heavy and light chains, connected by a small linker peptide. They are less immunogenic than complete immunoglobulin and thus have potential therapeutic use.
Weapons
Devices or tools used in combat or fighting in order to kill or incapacitate.
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