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Synthesis of Oligosaccharides from the Inner Core Structure of Haemophilus Influenzae and Neisseria meningitidis Lipopolysaccharides
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2006 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis describes the synthesis of oligosaccharides corresponding to different parts of the lipopolysaccharide (LPS) inner core structure from Haemophilus influenzae and Neisseria meningitidis. Chapter 2 describes the synthesis of a protected trisaccharide common to H. influenzae and N. meningitidis LPS, which can be used as a versatile precursor in further syntheses of larger LPS structures. In Chapter 3 syntheses towards phosphoethanolamine substituted trisaccharides corresponding to H. influenzae and N. meningitidis structures are presented. In Chapter 4 the synthesis of a H. influenzae tetrasaccharide structure, with and without a phosphoethanolamine substituent in the 6-position of the second heptose unit, is described. Conjugation to biotin of these two tetrasaccharides is also performed. Chapter 5 describes the synthesis of a spacer-equipped Kdo acceptor that is subsequently attached to the tetrasaccharide described in Chapter 4 forming a pentasaccharide from the inner core structure of H. influenzae. Similar to the synthesis of the tetrasaccharide, a phosphoethanolamine is attached to the 6 position of the second heptose. Chapter 5 also describes the synthesis of various Kdo thioglycoside donors and their evaluation in glycosylation reactions using different promoters and reaction conditions.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi , 2006.
Keyword [en]
Carbohydrate, synthesis, Haemophilus influenzae, Neisseria meningitidis
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-894ISBN: 91-7155-217-0 (print)OAI: oai:DiVA.org:su-894DiVA: diva2:200606
Public defence
2006-03-31, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 10:00
Opponent
Supervisors
Available from: 2006-03-09 Created: 2006-03-09Bibliographically approved
List of papers
1. Synthesis of the Branched Trisaccharide L-Glycero-α-D-manno-heptopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→4)]-L-glycero-α-D-manno-heptopyranose, Protected to Allow Flexible Access to Neisseria and Haemophilus LPS Inner Core Structures
Open this publication in new window or tab >>Synthesis of the Branched Trisaccharide L-Glycero-α-D-manno-heptopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→4)]-L-glycero-α-D-manno-heptopyranose, Protected to Allow Flexible Access to Neisseria and Haemophilus LPS Inner Core Structures
2004 In: Journal of carbohydrate chemistry, ISSN 0732-8303, Vol. 23, no 8&9, 443-452 p.Article in journal (Refereed) Published
Identifiers
urn:nbn:se:su:diva-25821 (URN)
Note
Part of urn:nbn:se:su:diva-894Available from: 2006-03-09 Created: 2006-03-09Bibliographically approved
2. Synthesis of Phosphoethanolamine-substituted Trisaccharides Corresponding to Neisseria meningitidis and Haemophilus influenzae LPS Structures
Open this publication in new window or tab >>Synthesis of Phosphoethanolamine-substituted Trisaccharides Corresponding to Neisseria meningitidis and Haemophilus influenzae LPS Structures
Manuscript (Other academic)
Identifiers
urn:nbn:se:su:diva-25822 (URN)
Note
Part of urn:nbn:se:su:diva-894Available from: 2006-03-09 Created: 2006-03-09 Last updated: 2010-01-13Bibliographically approved
3. Synthesis of glycero-α-D-manno-heptopyranosyl-(1→2)-(6-O-aminoethylphosphono-L-glycero-α-D-manno-heptopyranosyl)-(1→3)-[β-D-glucopyranosyl-(1→4)]-L-glycero-α-D-manno-heptopyranose: A common tetrasaccharide motif of Haemophilus influenzae LPS inner core structures
Open this publication in new window or tab >>Synthesis of glycero-α-D-manno-heptopyranosyl-(1→2)-(6-O-aminoethylphosphono-L-glycero-α-D-manno-heptopyranosyl)-(1→3)-[β-D-glucopyranosyl-(1→4)]-L-glycero-α-D-manno-heptopyranose: A common tetrasaccharide motif of Haemophilus influenzae LPS inner core structures
In: Organic & Biomolecular ChemistryArticle in journal (Refereed) Accepted
Identifiers
urn:nbn:se:su:diva-25823 (URN)
Note
Part of urn:nbn:se:su:diva-894Available from: 2006-03-09 Created: 2006-03-09Bibliographically approved
4. Evaluation of Thioglycosides of Kdo as Glycosyl Donor
Open this publication in new window or tab >>Evaluation of Thioglycosides of Kdo as Glycosyl Donor
2007 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 342, no 3-4, 631-637 p.Article in journal (Refereed) Published
Abstract [en]

The use of Kdo thioglycosides as glycosyl donors using DMTST, IBr/AgOTf and NIS/AgOTf as promoters has been evaluated. Activation at low temperature allowed to escape the formation of 2,3-glycal byproducts to give glycosides in high yield and with good β-anomeric selectivity. The use of diethyl ether as solvent and (especially) isopropylidene acetals as protecting groups improved the α-anomeric selectivity. NIS/AgOTf as promoter surprisingly yielded the 3-iodo-product via the glycal intermediate.

Place, publisher, year, edition, pages
Elsevier, 2007
Keyword
Thioglycoside donors; Kdo glycosides; Thiophilic promoters
National Category
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-25824 (URN)10.1016/j.carres.2006.08.021 (DOI)000244548700028 ()
Note
Part of urn:nbn:se:su:diva-894Available from: 2006-03-09 Created: 2006-03-09 Last updated: 2017-12-13Bibliographically approved
5. Synthesis ofHaemophilus influenzae LPS
Open this publication in new window or tab >>Synthesis ofHaemophilus influenzae LPS
Manuscript (Other academic)
Identifiers
urn:nbn:se:su:diva-25825 (URN)
Note
Part of urn:nbn:se:su:diva-894Available from: 2006-03-09 Created: 2006-03-09 Last updated: 2010-01-13Bibliographically approved

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