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Synthesis of lactosamine-containing carbohydrate structures and development for their easy assembly and conjugation
Stockholm University.
1999 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis is based on four publications. The first chapter describes preparation of anomerically pure thioethyl-, thiophenyl-, and n-pentenyl 2-azido-2-deoxy glycosyl building blocks from easily accessible per-acetylated glycosamines.

In the second part, acetylated, benzylated and non-protected n-pentenyl glycosides are used as substrates for preparing various spacer functionalities, which are obtained by means of radical elongations, oxidations and reductions.

The syntheses of a trisaccharide,a-D-GlcpNAc-(1-->4)-b-D-Galp-(1-->4)-b-D-GlcpNAc, and fragments thereof, linked to a long lipophilic aglycon, are described in the third part. For the formation of theb-D-Galp-(1-->4)-D-GlcpNAc bond, several differently protected glucosamine acceptors were prepared and their reactivity towards a disaccharide donor evaluated.

Finally, lactosamine derivatives were prepared by regioselective galactosylation and used as building blocks in the chemical synthesis of various oligosaccharides. The syntheses of polylactosamine di-, tri- and tetramers were achieved by regioselective glycosylation. Also spacer containing sulfated N-acetyllactosamine and Lewis x structures were synthesised.

Place, publisher, year, edition, pages
Stockholm: Stockholm University , 1999. , 73 p.
National Category
Organic Chemistry
Research subject
Organic Chemistry
URN: urn:nbn:se:su:diva-64916ISBN: 91-7265-022-2OAI: diva2:459794
Public defence
1999-11-25, 10:00
Härtill 4 uppsatserAvailable from: 2011-11-28 Created: 2011-11-28Bibliographically approved

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