{"id":{"repo_id":"cape-town","oai_identifier":"oai:open.uct.ac.za:11427/6291"},"canonical_url":"https://search.dev.ndltd.org/etd/cape-town/oai:open.uct.ac.za:11427/6291","repository":{"repo_id":"cape-town","name":"University of Cape Town","base_url":"https://open.uct.ac.za/oai/request"},"display":{"title":"Synthesis and inclusion studies of stable allicin mimics as novel antimicrobial agents","abstract":"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.","abstract_html":"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.","abstract_has_math":false,"creators":["Stellenboom, Nashia"],"institution":"Department of Chemistry","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":["Hunter, Roger","Caira, Mino R"],"committee_chairs":[],"committee_members":[],"year":2008,"date_issued":"2008","date_published":"2008","updated_at":"2026-07-22T22:22:39Z","subjects":[],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/11427/6291","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Hunter, Roger","Caira, Mino R"]},{"key":"dc:creator","label":"Author","values":["Stellenboom, Nashia"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2014-08-13T14:25:51Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2014-08-13T14:25:51Z"]},{"key":"dc:date.issued","label":"Date","values":["2008"]},{"key":"dc:publisher.department","label":"Dc Publisher Department","values":["Department of Chemistry"]},{"key":"dc:publisher.institution","label":"Dc Publisher Institution","values":["University of Cape Town"]},{"key":"dc:type","label":"Dc Type","values":["Doctoral Thesis"]},{"key":"dc:type.qualificationlevel","label":"Dc Type Qualificationlevel","values":["Doctoral"]},{"key":"dc:type.qualificationname","label":"Dc Type Qualificationname","values":["PhD"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["eng"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["http://hdl.handle.net/11427/6291"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Includes abstract.","Includes bibliographical references (p. 193-202)."]},{"key":"dc:description.abstract","label":"Abstract","values":["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."]},{"key":"dc:title","label":"Title","values":["Synthesis and inclusion studies of stable allicin mimics as novel antimicrobial agents"]}]}],"canonical_facts":{"dc:contributor.advisor":["Hunter, Roger","Caira, Mino R"],"dc:creator":["Stellenboom, Nashia"],"dc:date.accessioned":["2014-08-13T14:25:51Z"],"dc:date.available":["2014-08-13T14:25:51Z"],"dc:date.issued":["2008"],"dc:description":["Includes abstract.","Includes bibliographical references (p. 193-202)."],"dc:description.abstract":["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."],"dc:identifier.uri":["http://hdl.handle.net/11427/6291"],"dc:language.iso":["eng"],"dc:publisher.department":["Department of Chemistry"],"dc:publisher.institution":["University of Cape Town"],"dc:title":["Synthesis and inclusion studies of stable allicin mimics as novel antimicrobial agents"],"dc:type":["Doctoral Thesis"],"dc:type.qualificationlevel":["Doctoral"],"dc:type.qualificationname":["PhD"]},"updated_at":"2026-07-22T22:22:39Z"}