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Synthesis and self-assembly of galactose-terminated alkanethiols and their ability to resist proteins
Linköping University, Department of Physics, Chemistry and Biology, Chemistry. Linköping University, The Institute of Technology.
Linköping University, Department of Physics, Chemistry and Biology, Chemistry. Linköping University, The Institute of Technology.
Linköping University, Department of Physics, Chemistry and Biology. Linköping University, The Institute of Technology.
2005 (English)In: Langmuir, ISSN 0743-7463, E-ISSN 1520-5827, Vol. 21, no 7, 2971-2980 p.Article in journal (Refereed) Published
Abstract [en]

The synthesis of two galactose-terminated alkanethiols with the structural formula X−OC2H5NHCO(CH2)15SH (X = 2,3,4,6-tetra-O-methyl-β-d-Gal or β-d-Gal) is described. Single-component and mixed self-assembled monolayers (SAMs) of the methylated and nonmethylated compounds were prepared on gold and subsequently characterized with ellipsometry, contact angle goniometry, and infraredreflection−absorption spectroscopy. Studies of the irreversible protein adsorption onto the SAMs using ex-situ ellipsometry revealed very low levels of fibrinogen and lysozyme adsorption onto mixed SAMs displaying advancing water contact angles between 24° and 45° and below 45°, respectively. A monomethylated compound (X = 6-O-methyl-β-d-Gal) was also synthesized and assembled on gold. This particular compound was found to possess wettability properties corresponding to the low adsorption regime of the mixed SAMs, and the results from the same set of fibrinogen and lysozyme adsorption experiments showed very low levels of protein adsorption. Our findings suggest that the protein rejecting properties rely on a fine balance between the surface energy and/or hydrogen bond donating/accepting properties of the SAM surface.

Place, publisher, year, edition, pages
2005. Vol. 21, no 7, 2971-2980 p.
National Category
Natural Sciences
Identifiers
URN: urn:nbn:se:liu:diva-24645DOI: 10.1021/la047203bLocal ID: 6831OAI: oai:DiVA.org:liu-24645DiVA: diva2:244967
Available from: 2009-10-07 Created: 2009-10-07 Last updated: 2017-12-13
In thesis
1. Synthesis of inositolphosphoglycans found in Trypanosoma cruzi and development of novel carbohydrate monomolecular layers
Open this publication in new window or tab >>Synthesis of inositolphosphoglycans found in Trypanosoma cruzi and development of novel carbohydrate monomolecular layers
2005 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

In this thesis, synthetic carbohydrate chemistry has been utilized to contribute to the fundamental understanding of three biological relevant areas. These include parasite cell-membrane glycoconjugates, protein-resistant surfaces and antifreeze glycoproteins.

The synthesis of inositolphosphoglycans found in Trypanosoma cruzi, the pathogen of Chagas´ disease, is described. A protected derivative of 6-(2-aminoethyl phosphonic acid)-2-amino-2-deoxy-α-D-glucopyranosyl-(1→6)-D-myo-inositol-1-phosphate was identified as an appropriate acceptor to give a synthetic route to the core oligosaccharide of T. cruzi glycoinositolphospholipids. The assembly of three building blocks accomplished the synthesis of the heptasaccharyl myo-inositol Galf(β1→3)-Manp(α1→2)-[Galf(β1→3)]-Manp(α1→2)-Manp(α1→6)-Manp(α1→4)-6-(2 -aminoethyl phosphonic acid)-GlcNp-(α1→6)-myo-Ins-1-PO4, the glycan of the T. cruzi lipopeptidophosphoglycan.

Carbohydrate self-assembled monolayers (SAMs) on gold were designed, synthesized and characterized to investigate their protein rejecting properties. Synthesis of methylated and non-methylated galactose-terminated alkanethiols provided mixed carbohydrate monomolecular layers. The physiochemical properties of the mixed SAMs were elucidated with ellipsometry, infrared reflection-absorption spectroscopy and contact angle goniometry. The irreversible adsorption of the model proteins fibrinogen and lysozyme was determined with ex-situ ellipsometry. Neither of the proteins adsorbed within a mixed regime corresponding to contact angles of water between 24° and 45°.

A carbohydrate model system mimicking the properties of antifreeze glycoproteins was developed. A Gal(β1→3)-GalNAc terminated 16-mercapto-hexadecanoic acid derivative was synthesized and co-adsorbed with an ethyl-terminated thiol in various proportions to form mixed SAMs on gold. The monolayers were characterized and the antifreeze model system was evaluated by initial ice nucleation studies.

Synthetic routes to protected ethyl 2-deoxy-2-phthalimido-1-β-D-thio-galactosamine derivatives via epimerization of corresponding glucosamine compounds were explored to provide methods in future synthesis of antifreeze glycoproteins and analogues.

Place, publisher, year, edition, pages
Linköping: Linköpings universitet, 2005. 63 p.
Series
Linköping Studies in Science and Technology. Dissertations, ISSN 0345-7524 ; 980
National Category
Natural Sciences
Identifiers
urn:nbn:se:liu:diva-29937 (URN)15363 (Local ID)91-85457-56-6 (ISBN)15363 (Archive number)15363 (OAI)
Public defence
2005-12-02, Planck, Fysikhuset, Campus Valla, Linköpings universitet, Linköping, 10:15 (English)
Opponent
Available from: 2009-10-09 Created: 2009-10-09 Last updated: 2012-12-04Bibliographically approved

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Hederos, MarkusKonradsson, PeterLiedberg, Bo

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