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Design and synthesis of glycose-derivatives and related molecules for cell membrane mimetics
Linköping University, Department of Physics, Measurement Technology, Biology and Chemistry. Linköping University, The Institute of Technology.
2004 (English)Licentiate thesis, monograph (Other academic)
Abstract [en]

A series of glucopyranose (α-D-glucose, β-D-glucose, D-gluconic acid and 6-amino-6-deoxy-D-glocuse) terminated alkanethiol acetals have been successfully synthesized. α and β-D-glucose were configured in controlled ways coupling with alkanethiol, in which bromosugar and trichloroacetirnidates were selected as activated glycosyl donors using different promoters tetraalkylammonium bromide (Et4NBr) and trimethylsilanetriflate (TMSOTf) respectively.

The glycosylation of glucuronic acid and 6-amino-6-deoxy-β-D-glucose to ω-mercaptohexadecanol depends on powerful donors and stronger promoters. The corresponding trichloroacetimidates of the methyl D-glucuronic ester and 6-azido-6-deoxy-β-D-glucose were used as active donors, and strong Lewis acid, trimethylsilyl triflate (TMSOTf) was also involved in this study.

These structures were mixed in different proportions with HO(CH2)16SH, and the corresponding SAMs on gold were characterized by ellipsometry, contact angle goniometry, and infrared reflection-absorption spectroscopy. Infrared reflection­absorption spectroscopy (IRAS) indicated well-ordered SAMs with a high degree of crystallinity on the hydrocarbon layer. Different orientation between α and β-D-glucose self-assembled monolayers, and the functionality of carboxyl acid and amine were explored on surface for further immobilization of lipid bilayers.

New model systems were developed, in which amphiphilic hexadecly OEG derivative or glucose derivatives were designed to present self-assembled monolayers on gold. HS(CH2)15CONH-EG6-CH2CONH(CH2)15CH3 displayed particularly sharp features in IRAS spectra at room temperature. Carbohydrate unit instead of OEG moiety could be more natural and it possesses three-dimensional water-filled space.

Place, publisher, year, edition, pages
Linköping: Linköpings universitet , 2004. , p. 42
Series
Linköping Studies in Science and Technology. Thesis, ISSN 0280-7971 ; 1108
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:liu:diva-153003Local ID: LiU-TEK-LIC-2004:37ISBN: 9173739979 (print)OAI: oai:DiVA.org:liu-153003DiVA, id: diva2:1282673
Available from: 2019-01-29 Created: 2019-01-25 Last updated: 2019-05-09Bibliographically approved

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Shi, Jing

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Department of Physics, Measurement Technology, Biology and ChemistryThe Institute of Technology
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