Synthesis and inclusion studies of stable allicin mimics as novel antimicrobial agents

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dc.contributor.advisorHunter, Rogeren_ZA
dc.contributor.advisorCaira, Mino Ren_ZA
dc.contributor.authorStellenboom, Nashiaen_ZA
dc.date.accessioned2014-08-13T14:25:51Z
dc.date.available2014-08-13T14:25:51Z
dc.date.issued2008en_ZA
dc.descriptionIncludes abstract.en_ZA
dc.descriptionIncludes bibliographical references (p. 193-202).en_ZA
dc.description.abstractAllicin, a known constituent of garlic, is a potent but unstable antimicrobial agent. Consideration of the underlying features responsible for allicin’s activity, as well as its instability, prompted an investigation into substituted S-aryl alkylthiosulfinates as a class of potential allicin mimics with enhanced stability. Synthesis of the targets also inspired development of a novel unsymmetrical disulfide synthesis. This thesis describes the development of a new methodology for synthesizing unsymmetrical disulfides. The synthesis involves converting a thiol to a sulfenylating agent by 1-chlorobenzotriazole (BtCl) in the presence of 1,2,3-benzotriazole (BtH). Addition of a second thiol affords unsymmetrical disulfides in excellent yields. In addition to being a one-pot methodology, the approach offers attractive environmentally friendly and cost-saving aspects. The methodology proved to be versatile, producing all types of unsymmetrical disulfides; aromatic-aliphatic disulfides, aromatic-aromatic disulfides as well as aliphatic-aliphatic disulfides including unsymmetrical cysteine disulfides.en_ZA
dc.identifier.apacitationStellenboom, N. (2008). <i>Synthesis and inclusion studies of stable allicin mimics as novel antimicrobial agents</i>. (Thesis). University of Cape Town ,Faculty of Science ,Department of Chemistry. Retrieved from http://hdl.handle.net/11427/6291en_ZA
dc.identifier.chicagocitationStellenboom, Nashia. <i>"Synthesis and inclusion studies of stable allicin mimics as novel antimicrobial agents."</i> Thesis., University of Cape Town ,Faculty of Science ,Department of Chemistry, 2008. http://hdl.handle.net/11427/6291en_ZA
dc.identifier.citationStellenboom, N. 2008. Synthesis and inclusion studies of stable allicin mimics as novel antimicrobial agents. University of Cape Town.en_ZA
dc.identifier.ris TY - Thesis / Dissertation AU - Stellenboom, Nashia AB - Allicin, a known constituent of garlic, is a potent but unstable antimicrobial agent. Consideration of the underlying features responsible for allicin’s activity, as well as its instability, prompted an investigation into substituted S-aryl alkylthiosulfinates as a class of potential allicin mimics with enhanced stability. Synthesis of the targets also inspired development of a novel unsymmetrical disulfide synthesis. This thesis describes the development of a new methodology for synthesizing unsymmetrical disulfides. The synthesis involves converting a thiol to a sulfenylating agent by 1-chlorobenzotriazole (BtCl) in the presence of 1,2,3-benzotriazole (BtH). Addition of a second thiol affords unsymmetrical disulfides in excellent yields. In addition to being a one-pot methodology, the approach offers attractive environmentally friendly and cost-saving aspects. The methodology proved to be versatile, producing all types of unsymmetrical disulfides; aromatic-aliphatic disulfides, aromatic-aromatic disulfides as well as aliphatic-aliphatic disulfides including unsymmetrical cysteine disulfides. DA - 2008 DB - OpenUCT DP - University of Cape Town LK - https://open.uct.ac.za PB - University of Cape Town PY - 2008 T1 - Synthesis and inclusion studies of stable allicin mimics as novel antimicrobial agents TI - Synthesis and inclusion studies of stable allicin mimics as novel antimicrobial agents UR - http://hdl.handle.net/11427/6291 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/6291
dc.identifier.vancouvercitationStellenboom N. Synthesis and inclusion studies of stable allicin mimics as novel antimicrobial agents. [Thesis]. University of Cape Town ,Faculty of Science ,Department of Chemistry, 2008 [cited yyyy month dd]. Available from: http://hdl.handle.net/11427/6291en_ZA
dc.language.isoengen_ZA
dc.publisher.departmentDepartment of Chemistryen_ZA
dc.publisher.facultyFaculty of Scienceen_ZA
dc.publisher.institutionUniversity of Cape Town
dc.subject.otherChemistryen_ZA
dc.titleSynthesis and inclusion studies of stable allicin mimics as novel antimicrobial agentsen_ZA
dc.typeDoctoral Thesis
dc.type.qualificationlevelDoctoral
dc.type.qualificationnamePhDen_ZA
uct.type.filetypeText
uct.type.filetypeImage
uct.type.publicationResearchen_ZA
uct.type.resourceThesisen_ZA
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