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Synthesis of methyl 3-amino-3,6-dideoxy-alpha-d-galactopyranoside carrying different amide substituents
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.
2013 (English)In: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 3, no 45, p. 23090-23097Article in journal (Refereed) Published
Abstract [en]

Bacterial polysaccharides may contain rare sugars of different stereochemistry and diverse functional groups; the repertoire can be further extended by varying the exocyclic substituents. Synthesis of four monosaccharides is described utilizing a suitably protected key intermediate obtained by regioselective acetal ring-opening reduction, dexoygenation at C6, alcohol oxidation at C3 followed by formation of an oxime, which was stereoselectively reduced by samarium diiodide to give a 3-amino-derivative having the desired galacto-configuration. Subsequent functionalization was performed resulting in one to four carbon atoms in the amide substituent.

Place, publisher, year, edition, pages
2013. Vol. 3, no 45, p. 23090-23097
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-97407DOI: 10.1039/c3ra45092aISI: 000326395800056OAI: oai:DiVA.org:su-97407DiVA, id: diva2:678019
Funder
Swedish Research CouncilKnut and Alice Wallenberg Foundation
Note

AuthorCount:3;

Available from: 2013-12-11 Created: 2013-12-09 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
Keyword
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)
Opponent
Supervisors
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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