{"id":{"repo_id":"dundee","oai_identifier":"oai:discovery.dundee.ac.uk:studenttheses/c9bd8401-6573-4bd9-95ad-db7835a225c1"},"canonical_url":"https://search.dev.ndltd.org/etd/dundee/oai:discovery.dundee.ac.uk:studenttheses/c9bd8401-6573-4bd9-95ad-db7835a225c1","repository":{"repo_id":"dundee","name":"University of Dundee","base_url":"https://discovery.dundee.ac.uk/ws/oai"},"display":{"title":"Synthesis of fragments of the capsular polysaccharide of <i>Neisseria meningitidis</i> (serogroup A) suitable for bioconjugation","abstract":"One of the causative agents of meningitis is the gram-negative bacteria Neisseria meningitidis. In the region known as the African meningitis belt, N. meningitidis serotype A is endemic in the population and is also known to cause large scale epidemics. An important virulence factor of this bacterium is the presence of a capsular polysaccharide (CPS) and apart from being an important surface antigen, also protects the bacteria cells against phagocytosis by the host’s immune defense. The CPS structure of the serotype A is the (1-6)-linked poly(3-O-acetyl-2-acetamido-2-deoxy-a-D-mannosyl phosphate):<br/>A potential route towards a vaccine would be to synthetically produce fragments of the CPS. In order to synthesise these CPS structures (1), the monosaccharide precursors 2-5 must be prepared first with temporary protection of the O-6 position and a permanent protection at the O-4 position. Formation and elongation of the CPS oligomers proceeds through the condensation of anomeric H-phosphonates 6. In order to accommodate this, compounds 2-5 allow for hydrolysis at the position-1 to the corresponding hemi-acetals. These are then converted to the H-phosphonates 6 before coupling to a monohydroxyl unit (structures 8) to form a phosphodiester linkage. Removal of the temporary protection at O-6 then gives the free hydroxyl (structures 7) needed for the chain elongation to continue. The fragments then will be capped with ethanolamine H-phosphonate 9 that will allow for conjugation to a protein carrier.","abstract_html":"One of the causative agents of meningitis is the gram-negative bacteria Neisseria meningitidis. In the region known as the African meningitis belt, N. meningitidis serotype A is endemic in the population and is also known to cause large scale epidemics. An important virulence factor of this bacterium is the presence of a capsular polysaccharide (CPS) and apart from being an important surface antigen, also protects the bacteria cells against phagocytosis by the host’s immune defense. The CPS structure of the serotype A is the (1-6)-linked poly(3-O-acetyl-2-acetamido-2-deoxy-a-D-mannosyl phosphate):&lt;br/&gt;A potential route towards a vaccine would be to synthetically produce fragments of the CPS. In order to synthesise these CPS structures (1), the monosaccharide precursors 2-5 must be prepared first with temporary protection of the O-6 position and a permanent protection at the O-4 position. Formation and elongation of the CPS oligomers proceeds through the condensation of anomeric H-phosphonates 6. In order to accommodate this, compounds 2-5 allow for hydrolysis at the position-1 to the corresponding hemi-acetals. These are then converted to the H-phosphonates 6 before coupling to a monohydroxyl unit (structures 8) to form a phosphodiester linkage. Removal of the temporary protection at O-6 then gives the free hydroxyl (structures 7) needed for the chain elongation to continue. The fragments then will be capped with ethanolamine H-phosphonate 9 that will allow for conjugation to a protein carrier.","abstract_has_math":false,"creators":["Black, Alan"],"institution":"University of Dundee","degree_name":"Doctor of Philosophy","degree_level":"Doctoral Thesis","degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2014,"date_issued":"2014","date_published":"2014","updated_at":"2026-07-24T02:08:05Z","subjects":[],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["oai:discovery.dundee.ac.uk:studenttheses/c9bd8401-6573-4bd9-95ad-db7835a225c1"],"render_values":[{"text":"oai:discovery.dundee.ac.uk:studenttheses/c9bd8401-6573-4bd9-95ad-db7835a225c1","href":null,"code":true}]}]},"links":{"outbound_url":"https://discovery.dundee.ac.uk/en/studentTheses/c9bd8401-6573-4bd9-95ad-db7835a225c1","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.sponsor","label":"Sponsor","values":["Biotechnology and Biological Sciences Research Council"]},{"key":"dc:creator","label":"Author","values":["Black, Alan"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2014"]},{"key":"dc:date.issued","label":"Date","values":["2014"]},{"key":"dc:publisher.department","label":"Dc Publisher Department","values":["Biological Chemistry and Drug Discovery"]},{"key":"dc:publisher.institution","label":"Dc Publisher Institution","values":["University of Dundee"]},{"key":"dc:relation.isreferencedby","label":"Dc Relation Isreferencedby","values":["https://discovery.dundee.ac.uk/en/studentTheses/c9bd8401-6573-4bd9-95ad-db7835a225c1"]},{"key":"dc:type","label":"Dc Type","values":["Thesis"]},{"key":"dc:type.qualificationlevel","label":"Dc Type Qualificationlevel","values":["Doctoral Thesis"]},{"key":"dc:type.qualificationname","label":"Dc Type Qualificationname","values":["Doctor of Philosophy"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["eng"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["oai:discovery.dundee.ac.uk:studenttheses/c9bd8401-6573-4bd9-95ad-db7835a225c1","https://discovery.dundee.ac.uk/en/studentTheses/c9bd8401-6573-4bd9-95ad-db7835a225c1"]},{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://discovery.dundee.ac.uk/files/6432004/AlanBlack2014.pdf"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["One of the causative agents of meningitis is the gram-negative bacteria Neisseria meningitidis. In the region known as the African meningitis belt, N. meningitidis serotype A is endemic in the population and is also known to cause large scale epidemics. An important virulence factor of this bacterium is the presence of a capsular polysaccharide (CPS) and apart from being an important surface antigen, also protects the bacteria cells against phagocytosis by the host’s immune defense. The CPS structure of the serotype A is the (1-6)-linked poly(3-O-acetyl-2-acetamido-2-deoxy-a-D-mannosyl phosphate):<br/>A potential route towards a vaccine would be to synthetically produce fragments of the CPS. In order to synthesise these CPS structures (1), the monosaccharide precursors 2-5 must be prepared first with temporary protection of the O-6 position and a permanent protection at the O-4 position. Formation and elongation of the CPS oligomers proceeds through the condensation of anomeric H-phosphonates 6. In order to accommodate this, compounds 2-5 allow for hydrolysis at the position-1 to the corresponding hemi-acetals. These are then converted to the H-phosphonates 6 before coupling to a monohydroxyl unit (structures 8) to form a phosphodiester linkage. Removal of the temporary protection at O-6 then gives the free hydroxyl (structures 7) needed for the chain elongation to continue. The fragments then will be capped with ethanolamine H-phosphonate 9 that will allow for conjugation to a protein carrier."]},{"key":"dc:title","label":"Title","values":["Synthesis of fragments of the capsular polysaccharide of <i>Neisseria meningitidis</i> (serogroup A) suitable for bioconjugation"]}]}],"canonical_facts":{"dc:contributor.sponsor":["Biotechnology and Biological Sciences Research Council"],"dc:creator":["Black, Alan"],"dc:date":["2014"],"dc:date.issued":["2014"],"dc:description.abstract":["One of the causative agents of meningitis is the gram-negative bacteria Neisseria meningitidis. In the region known as the African meningitis belt, N. meningitidis serotype A is endemic in the population and is also known to cause large scale epidemics. An important virulence factor of this bacterium is the presence of a capsular polysaccharide (CPS) and apart from being an important surface antigen, also protects the bacteria cells against phagocytosis by the host’s immune defense. The CPS structure of the serotype A is the (1-6)-linked poly(3-O-acetyl-2-acetamido-2-deoxy-a-D-mannosyl phosphate):<br/>A potential route towards a vaccine would be to synthetically produce fragments of the CPS. In order to synthesise these CPS structures (1), the monosaccharide precursors 2-5 must be prepared first with temporary protection of the O-6 position and a permanent protection at the O-4 position. Formation and elongation of the CPS oligomers proceeds through the condensation of anomeric H-phosphonates 6. In order to accommodate this, compounds 2-5 allow for hydrolysis at the position-1 to the corresponding hemi-acetals. These are then converted to the H-phosphonates 6 before coupling to a monohydroxyl unit (structures 8) to form a phosphodiester linkage. Removal of the temporary protection at O-6 then gives the free hydroxyl (structures 7) needed for the chain elongation to continue. The fragments then will be capped with ethanolamine H-phosphonate 9 that will allow for conjugation to a protein carrier."],"dc:identifier":["oai:discovery.dundee.ac.uk:studenttheses/c9bd8401-6573-4bd9-95ad-db7835a225c1","https://discovery.dundee.ac.uk/en/studentTheses/c9bd8401-6573-4bd9-95ad-db7835a225c1"],"dc:identifier.uri":["https://discovery.dundee.ac.uk/files/6432004/AlanBlack2014.pdf"],"dc:language":["eng"],"dc:publisher.department":["Biological Chemistry and Drug Discovery"],"dc:publisher.institution":["University of Dundee"],"dc:relation.isreferencedby":["https://discovery.dundee.ac.uk/en/studentTheses/c9bd8401-6573-4bd9-95ad-db7835a225c1"],"dc:title":["Synthesis of fragments of the capsular polysaccharide of <i>Neisseria meningitidis</i> (serogroup A) suitable for bioconjugation"],"dc:type":["Thesis"],"dc:type.qualificationlevel":["Doctoral Thesis"],"dc:type.qualificationname":["Doctor of Philosophy"]},"updated_at":"2026-07-24T02:08:05Z"}