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Efficient routes to ethyl-2-deoxy-2-phthalimido-1-β-D-thio-galactosamine derivatives via epimerization of the corresponding glucosamine compounds
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.
2005 (English)In: Journal of carbohydrate chemistry, ISSN 0732-8303, E-ISSN 1532-2327, Vol. 24, no 3, 297-320 p.Article in journal (Refereed) Published
Abstract [en]

Short synthetic routes to protected ethyl 2-deoxy-2-phthalimido-1-β-D- thio-galactosamine derivatives via epimerization of the corresponding glucosamine compounds are described. Starting from D-glucosamine hydrochloride, the epimerizations were performed by displacement of presynthesized triflates with nitrite anions and by an oxidation/reduction route. The latter method involved Moffatt oxidation to the corresponding 4-ketohexoses and subsequent reduction using sodium borohydride/ tetrabutylammonium borohydride, zinc borohydride, or lithium tri-sec-butyl borohydride in THF. The displacement route was found to be the preferred method for epimerization of 3-O-acyl (benzoyl) derivatives. For glucosamine compounds with 3-O-etheral- (allyl or benzyl) and 6-O-benzyl protecting groups, the oxidation/reduction route was the most convenient procedure to achieve corresponding galactosamine compounds. The produced galactosamine derivatives will be useful building blocks in the synthesis of antifreeze glycoproteins substances and analogues thereof.

Place, publisher, year, edition, pages
2005. Vol. 24, no 3, 297-320 p.
Keyword [en]
Antifreeze glycoproteins, Epimerization, Galactosamine, Glycosyl donors, Oligosaccharides
National Category
Engineering and Technology
Identifiers
URN: urn:nbn:se:liu:diva-50380DOI: 10.1081/CAR-200061584OAI: oai:DiVA.org:liu-50380DiVA: diva2:271276
Available from: 2009-10-11 Created: 2009-10-11 Last updated: 2017-12-12
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, Peter

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