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Derivatization of a bioorthogonal protected trisaccharide linker: towards multimodal tools for chemical biology
Linköpings universitet, Institutionen för fysik, kemi och biologi, Organisk Kemi. Linköpings universitet, Tekniska fakulteten.
Linköpings universitet, Institutionen för fysik, kemi och biologi, Organisk Kemi. Linköpings universitet, Tekniska fakulteten.
Linköpings universitet, Institutionen för fysik, kemi och biologi, Organisk Kemi. Linköpings universitet, Tekniska högskolan.ORCID-id: 0000-0002-5582-140X
Linköpings universitet, Institutionen för fysik, kemi och biologi, Biokemi. Linköpings universitet, Tekniska högskolan.ORCID-id: 0000-0001-5827-3587
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2012 (Engelska)Ingår i: Bioconjugate chemistry, ISSN 1043-1802, E-ISSN 1520-4812, Vol. 23, nr 6, s. 1333-1340Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

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.

Ort, förlag, år, upplaga, sidor
American Chemical Society (ACS), 2012. Vol. 23, nr 6, s. 1333-1340
Nyckelord [en]
spacer molecule, oligosaccharide-based, cholesterol anchor, SPR, lipid rafts, click-chemistry
Nationell ämneskategori
Naturvetenskap
Identifikatorer
URN: urn:nbn:se:liu:diva-76735DOI: 10.1021/bc300160aISI: 000305358700027OAI: oai:DiVA.org:liu-76735DiVA, id: diva2:516517
Tillgänglig från: 2012-04-18 Skapad: 2012-04-18 Senast uppdaterad: 2018-04-25
Ingår i avhandling
1. Synthesis of Orthogonally Functionalized Oligosaccharides for Self-assembled Monolayers and as Multimodal Tools in Chemical Biology
Öppna denna publikation i ny flik eller fönster >>Synthesis of Orthogonally Functionalized Oligosaccharides for Self-assembled Monolayers and as Multimodal Tools in Chemical Biology
2012 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

This thesis covers different topics in the field of synthetic organic chemistry combined with the field of surface science and glycobiology.

First, the text presents a series of orthogonally protected oligosaccharides (tri-, penta-, and heptasaccharides) of varying length and structures, which are synthesized with the aim of developing novel heterobifunctional biocompatible cross-linkers. Successful conjugation with different chemical handles is also described and used to illustrate the potential implementation of defined carbohydrate based compounds have potential use in biosensing applications. The results of incubation experiments using living cells indicate that the linker is incorporated into cell surfaces and enriched in microdomains.

Second, synthesis of various saccharide-terminated alkane thiols immobilized on gold surfaces is reported. The protein adsorption and antifouling characteristics of these surfaces were investigated using model proteins and the common fouling organisms, Ulva linza and Balanus amphitrite.

Further, oligo(lactose)-based thiols (di-, tetra-, and hexasaccharides) were synthesized and immobilized on gold nanoparticles to investigate how well these rigid, rod-like oligosaccharides can stabilize such nanoparticles for future use in constructing hybrid nanoparticles.

Finally, the thesis describes synthesis of a systematic series of oligo(ethylene) glycols possessing either hydrogen- or methyl-terminated groups. Investigation of the fundamental characteristics of self-assembled monolayers, will give important insights into the design of protein repellant surfaces.

Ort, förlag, år, upplaga, sidor
Linköping: Linköping University Electronic Press, 2012. s. 65
Serie
Linköping Studies in Science and Technology. Dissertations, ISSN 0345-7524 ; 1442
Nyckelord
Oligosaccharide synthesis, glycosylation, thioglycosides, orthogonally protected, oligo(lactosides), spacer molecule, heterobifunctional, surface plasmon resonance, lipid anchor, self-assembled monolayers, glyconanoparticles
Nationell ämneskategori
Naturvetenskap
Identifikatorer
urn:nbn:se:liu:diva-76733 (URN)978-91-7519-906-1 (ISBN)
Disputation
2012-05-11, Planck, Fysikhuset, Campus Valla, Linköpings universitet, Linköping, 10:15 (Engelska)
Opponent
Handledare
Tillgänglig från: 2012-04-18 Skapad: 2012-04-18 Senast uppdaterad: 2019-12-08Bibliografiskt granskad

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