Solution and solid phase synthesis of N,N'-diacetyl chitotetraoses

The three major biopolymers, proteins, nucleic acids and glycoconjugates are mainly responsible for the information transfer, which is a fundamental process of life. The biological importance of proteins and nucleic acids are well explored and oligosaccharides in the form of glycoconjugates have gained importance recently. The β-(1→4) linked N-acetylglucosamine (GlcNAc) moiety is a frequently occurring structural unit in various naturally and biologically important oligosaccharides and related conjugates. Chitin which is the most abundant polymer of GlcNAc is widely distributed in nature whereas the related polysaccharide chitosan (polymer of GlcN and GlcNAc) occurs in certain fungi. Chitooligosaccharides of mixed acetylation patterns are of interest for the determination of the substrate specificities and mechanism of chitinases. In this report, we describe the chemical synthesis of three chitotetraoses namely GlcNAc-GlcN-GlcNAc-GlcN, GlcN-GlcNAc-GlcNAc-GlcN and GlcN-GlcN-GlcNAc-GlcNAc. Benzyloxycarbonyl (Z) and p-nitrobenzyloxycarbonyl (PNZ) were used for the amino functionality due to their ability to form the β-linkage during the glycosylation reactions through neighboring group participation and the trichloroacetimidate approach was utilized for the donor. Monomeric, dimeric acceptors and donors have been prepared by utilizing the Z and PNZ groups and coupling between the appropriate donor and acceptors in the presence of Lewis acid yielded the protected tetrasaccharides. Finally cleavage of PNZ followed by reacetylation and the deblocking of other protecting groups afforded the N,N’-diacetyl chitotetraoses in good yield. Successful syntheses for the protected diacetyl chitotetraoses by solid phase synthesis have also been described.

Level thesis:degree_level

thesis.doctoral

Grantor dc:publisher

Universität Potsdam

Year

2008

Author dc:creator

• Vijayakrishnan, Balakumar

Contributors dc:contributor

• Peter, Martin. G.

• Chitooligosaccharide
• Chemische Synthese
• Festphasensynthese
• Glykosylierung
• Chitooligosaccharides
• Chemical Synthesis
• Solution phase synthesis
• Solid phase synthesis
• Glycosylation

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/1713

OAI identifier oai:identifier

oai:kobv.de-opus4-uni-potsdam:1713