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

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.

Grantor dc:publisher.institution

Department of Chemistry

Year dc:date.issued

2008

Author dc:creator

• Stellenboom, Nashia

Advisors dc:contributor.advisor

• Hunter, Roger
• Caira, Mino R

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/11427/6291

OAI identifier oai:identifier

oai:open.uct.ac.za:11427/6291