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Synthesis of oligo(lactose)-based thiols and their self-assembly onto gold surfaces
Linköpings universitet, Institutionen för fysik, kemi och biologi, Kemi. Linköpings universitet, Tekniska fakulteten.
Linköpings universitet, Institutionen för fysik, kemi och biologi, Molekylär fysik. Linköpings universitet, Tekniska fakulteten.ORCID-id: 0000-0002-1639-5735
Linköpings universitet, Institutionen för fysik, kemi och biologi, Molekylär fysik. Linköpings universitet, Tekniska fakulteten.ORCID-id: 0000-0002-7001-9415
Nanyang Technology University, Singapore .
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2013 (Engelska)Ingår i: Colloids and Surfaces B: Biointerfaces, ISSN 0927-7765, E-ISSN 1873-4367, Vol. 105, s. 187-193Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

The ability to produce monomolecular coatings with well-defined structural and functional properties is of key importance in biosensing, drug delivery, and many recently developed applications of nanotechnology. Organic chemistry has proven to be a powerful tool to achieve this in many research areas. Herein, we present the synthesis of three oligo(lactosides) glycosylated in a (1 → 3) manner, and which are further functionalized with amide-linked short alkanethiol spacers. The oligosaccharides (di-, tetra-, and hexasaccharide) originate from the inexpensive and readily available lactose disaccharide. These thiolated derivatives were immobilized onto gold surfaces, and the thus formed self-assembled monolayers (SAMs) on planar gold were characterized by wettability, ellipsometry and infrared reflection–absorption spectroscopy. Further, the ability of these SAMs to stabilize gold nanoparticles in saline solutions was also demonstrated, indicating that the oligosaccharides may be used as stabilizing agents in gold nanoparticle-based assays.

Ort, förlag, år, upplaga, sidor
Elsevier, 2013. Vol. 105, s. 187-193
Nyckelord [en]
Oligosaccharides, Lactose, Self-assembled monolayers, Gold nanoparticles
Nationell ämneskategori
Teknik och teknologier
Identifikatorer
URN: urn:nbn:se:liu:diva-92697DOI: 10.1016/j.colsurfb.2013.01.002ISI: 000316589500027OAI: oai:DiVA.org:liu-92697DiVA, id: diva2:621669
Anmärkning

The previous status of this article was Manuscript.

Tillgänglig från: 2013-05-16 Skapad: 2013-05-16 Senast uppdaterad: 2017-05-31Bibliografiskt granskad
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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Fyrner, TimmyEderth, ThomasAili, DanielKonradsson, Peter

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