Synthesis of Oligosaccharides from the Inner Core Structure of Haemophilus Influenzae and Neisseria meningitidis Lipopolysaccharides
2006 (English)Doctoral thesis, comprehensive summary (Other academic)
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.
Carbohydrate, synthesis, Haemophilus influenzae, Neisseria meningitidis
IdentifiersURN: urn:nbn:se:su:diva-894ISBN: 91-7155-217-0OAI: oai:DiVA.org:su-894DiVA: diva2:200606
2006-03-31, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 10:00
Murphy, Paul, Dr
Oscarson, Stefan, Professor
List of papers