Victoria University

Synthesis of Sporidesmin Based Antigens

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dc.contributor.advisor Ferrier, R J Erasmuson, Anton Francis 2008-12-18T20:49:17Z 2008-12-18T20:49:17Z 1976 1976
dc.description.abstract In a program aimed at developing a chemically derived vaccine against sporidesmin-A, the toxin which causes the pasture disease facial eczema, two haptens have been prepared, coupled to protein carriers, and tested for immunogenicity. The hapten, 2-amino-5-chloro-3,4-dimethoxybenzyl alcohol has been synthesised from vanillin and the general synthetic methods developed in the course of this work have been used to prepare a large number of related vanillin derivatives for use in cross-hapten studies. The carbon-13 nuclear magnetic resonance spectra of 16 vanillin derivatives have been obtained, and two independent methods of deducing vanillin substitution patterns have been developed. 5-chloro-6, 7-dimethoxy-N-methyl-lH-indole has been prepared by a new route and its 3-oxoacetic acid derivative has been synthesized for use as a hapten. The Vilsmeier-Haack intermediate, l-methyl-3-(N,N-dimethylimonio) methyl-lH-indole chloride was isolated and a number of possible synthetic routes from it to pyrroloindoles were explored. The vanillin and indole haptens have been coupled to protein carriers to form antigens which generated a low antibody response. However, the use of mycobacterium phlei as a carrier greatly increased the antibody response but the antibodies produced did not interact strongly with sporidesmin-A. en_NZ
dc.language.iso en_NZ
dc.publisher Victoria University of Wellington en_NZ
dc.subject Antigens and antibodies en_NZ
dc.subject Medical chemistry en_NZ
dc.subject Sporidesmin en_NZ
dc.subject Haptens en_NZ
dc.subject Facial eczema en_NZ
dc.subject Pithecayces chartarum en_NZ
dc.title Synthesis of Sporidesmin Based Antigens en_NZ
dc.type Text en_NZ
vuwschema.contributor.unit School of Chemical and Physical Sciences en_NZ
vuwschema.subject.marsden 320299 Immunology en_NZ
vuwschema.subject.marsden 250406 Immunological and Bioassay Methods en_NZ
vuwschema.subject.marsden 320305 Medical Biochemistry: Proteins and Peptides en_NZ
vuwschema.type.vuw Awarded Doctoral Thesis en_NZ Chemistry en_NZ Victoria University of Wellington en_NZ Doctoral en_NZ Doctor of Philosophy en_NZ
vuwschema.subject.anzsrcfor 119999 Medical and Health Sciences not elsewhere classified en_NZ

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