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Variant synthetic pathway to glucuronic acid-containing di- and trisaccharide thioglycoside building blocks for continued synthesis of Cryptococcus neoformans capsular polysaccharide structures
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2008 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 343, no 12, 2200-2208 p.Article in journal (Refereed) Published
Abstract [en]

An alternative pathway to glucuronic acid-containing di- and trisaccharide thioglycoside building blocks, suitable for the synthesis of Cryptococcus neoformans capsular polysaccharide structures, has been developed. As opposed to our earlier synthesis, this approach features the introduction of the glucuronic acid motif at the di- and trisaccharide level through oxidation of a glucose residue. This approach circumvents problems encountered in glycosylations with glucuronic acid donors and benzylation of glucuronic acid-containing derivatives. Selective protection of primary alcohols was obtained at the di- and trisaccharide stage using TBDMS or trityl protecting groups, respectively. After benzylation of the secondary hydroxyl groups and subsequent removal of the TBDMS or trityl group, oxidation of the free primary alcohols to carboxylic acids was performed in high yield using the TEMPO–BAIB reagent mixture, which does not tend to oxidize thioglycosides. The new approach requires a number of extra steps, but has proven to be more reliable and easily reproducible.

Place, publisher, year, edition, pages
2008. Vol. 343, no 12, 2200-2208 p.
Identifiers
URN: urn:nbn:se:su:diva-14427DOI: 10.1016/j.carres.2007.11.026ISI: 000257823400032OAI: oai:DiVA.org:su-14427DiVA: diva2:180947
Available from: 2009-02-05 Created: 2009-02-05 Last updated: 2017-12-13Bibliographically approved
In thesis
1. Development of strategies for construction of thioglycoside building blocks corresponding to repeating triads of Cryptococcus neoformans GXM capsular polysaccharide
Open this publication in new window or tab >>Development of strategies for construction of thioglycoside building blocks corresponding to repeating triads of Cryptococcus neoformans GXM capsular polysaccharide
2010 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis focuses on the development of methods for synthesis of thioglycoside building blocks corresponding to the repeating units of the capsular polysaccharide (CPS) of Cryptococcus neoformans, an opportunistic fungal pathogen. The building blocks are suitable for construction of large synthetic oligosaccharides related to the native CPS-structures which are to be used in biological studies in order to identify protective epitopes with the aim to develop a glycoconjugate vaccine against C. neoformans infections.

Chapter 3 describes the improved synthesis of di- and trisaccharide glucuronic acid-containing thioglycoside blocks by introduction of the carboxylic acid motif at the di- and trisaccharide level through oxidation of a glucose residue. The new approach requires a number of extra steps, but has proven to be more reliable and more easily reproducible since problems encountered in glycosylations with glucuronic acid donors and benzylation of glucuronic acid-containing derivatives are circumvented.

In Chapter 4 the development of a synthetic route to xylose-substituted tri- and tetrasaccharide building blocks where the protecting group strategy allows for orthogonal glycosylations with thioglycoside acceptors is discussed.

Chapter 5 describes the synthetic pathway to the glucuronic acid-containing derivatives according to the methodology developed in Chapter 4 and the assembly of a hexasaccharide building block corresponding to the repeating triad of serotype A.

In Appendix І an alternative strategy for synthesis of glucuronic acid-substituted derivatives by direct introduction of a perbenzylated glucuronic acid trichloroacetimidate donor where stereoselectivity is achieved through the use of an 1,6-anhydro acceptor.

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2010. 51 p.
Keyword
Crytococcus neoformans, Capsular polysaccharide, Thioglycosides, Convergent synthesis
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-38967 (URN)978-91-7447-094-9 (ISBN)
Public defence
2010-06-02, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 14:00 (Swedish)
Opponent
Supervisors
Note
At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 2: Manuscript. Paper 3: Manuscript.Available from: 2010-05-11 Created: 2010-05-05 Last updated: 2010-05-07Bibliographically approved

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