Synthesis of Hetero-chitooligosaccharides

Chitooligosaccharides are composed of linear β-(1→4)-linked 2-acetamido-2-deoxy-β-D-glucopyranose (GlcNAc) and/or 2-amino-2-deoxy-β-D-glucopyranose (GlcN). They are of interest due to their remarkable biological properties including antibacterial, antitumor, antifungal and elicitor activities. They can be obtained from the aminoglucan chitosan by chemical or enzymatic degradation which obviously affords rather heterogenous mixtures. On the other hand, chemical synthesis provides pure compounds with defined sequences of GlcNAc and GlcN monomers. The synthesis of homo- and hetero-chitobioses and hetero-chitotetraoses is described in this thesis. Dimethylmaleoyl and phthaloyl groups were used for protection of the amines. The donor was activated as the trichloroacetimidate in order to form the β-linkages. Glycosylation in the presence of trimethylsilyl trifluoromethanesulfonate, followed by N- and O-deprotection furnished chitobioses and chitotetraoses in good yields.

Level thesis:degree_level

thesis.doctoral

Grantor dc:publisher

Universität Potsdam

Year

2008

Author dc:creator

• Issaree, Arisara

Contributors dc:contributor

• Peter, Martin G.

• Kohlenhydrate
• Chitooligosaccharide
• Glycosylierung
• Synthesemethoden
• Trichloracetimidate
• Carbohydrates
• Chitooligosaccharides
• Glycosylation
• Synthetic methods
• Trichloroacetimidates

Statement dc:rights

• Creative Commons - Namensnennung - Nicht-kommerziell - Keine Bearbeitung 3.0 Unported

Repository record source_url

https://publishup.uni-potsdam.de/frontdoor/index/index/docId/1552

OAI identifier oai:identifier

oai:kobv.de-opus4-uni-potsdam:1552