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Synthesis of ss-(1 -> 2)-Linked 6-Deoxy-L-altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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Number of Authors: 52017 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 82, no 6, p. 3062-3071Article in journal (Refereed) Published
Abstract [en]

The ss-(1 -> 2)-linked 6-deoxy-L-altropyranose di- to pentasaccharides 2-5, relevant to the O-antigen of the infectious Yersinia enterocolitica 0:3, were synthesized for the first time. The challenging 1,2-cis-altropyranosyl linkage was assembled effectively via glycosylation with 2-O-benzyl-3,4-di-O-benzoyl-6-deoxy-L-altropyranosyl ortho-hexynylbenzoate (7) under the catalysis of PPh3AuNTf2. NMR and molecular modeling studies showed that the pentasaccharide (5) adopted a left-handed helical conformation. [GRAPHICS]

Place, publisher, year, edition, pages
2017. Vol. 82, no 6, p. 3062-3071
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-142654DOI: 10.1021/acs.joc.7b00057ISI: 000397077500026PubMedID: 28230982OAI: oai:DiVA.org:su-142654DiVA, id: diva2:1095179
Available from: 2017-05-12 Created: 2017-05-12 Last updated: 2018-03-27Bibliographically approved
In thesis
1. Synthesis and analysis of carbohydrates related to bacterial polysaccharides
Open this publication in new window or tab >>Synthesis and analysis of carbohydrates related to bacterial polysaccharides
2018 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The outer surface of bacteria is composed of around 75% carbohydrates, which are vital for the bacteria to survive and communicate with the host biological system. The thesis discusses different properties of carbohydrates that are essential for understanding the bacterial behavior in biological systems. The first three chapters give an overview of carbohydrates.

The fourth chapter discusses the synthesis of four amide-substituted 3,6-dideoxy-α-D-galactopyranosides, namely, methyl α-3,6-dideoxy-3-formamido-, acetamido-, (R)-3-hydroxybutyramido-, and (4-hydroxybutyramido)-D-galactopyranoside. These sugars were found as components of some bacterial O-antigens; the study is a step toward the synthesis of oligosaccharides that contain them. The fifth chapter describes the exchange kinetics of the formyl and acetyl derivatives that were synthesized. Both of them have two conformational states for the amide side-chain. 13C-NMR saturation transfer experiments are utilized for these measurements to reveal more about their properties in solution.

In chaptr six, NMR and conformational analysis of oligosaccharides related to the O-antigen of Yersinia enterocolitica O:3 bacteria were carried out to obtain more information regarding their 3D structure.

Chapter seven is focusing on the development of CASPER, a program for rapid assignment of 1H- and 13C-NMR chemical shifts of bacterial lipopolysaccharides, by adding more sugars into its database and testing it for naturally occurring LPS as well as extending the scope for synthetic carbohydrates, which is planned to be developed further in the future.

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2018. p. 53
Keywords
carbohydrates, synthesis, conformation, NMR, O-antigen, computer-assisted structure elucidation
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-154449 (URN)978-91-7797-216-7 (ISBN)978-91-7797-217-4 (ISBN)
Public defence
2018-05-15, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (English)
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Note

At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 4: Manuscript.

Available from: 2018-04-20 Created: 2018-03-27 Last updated: 2018-04-23Bibliographically approved

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