The thiol-ene coupling reaction is emerging as an important conjugation reaction that is suitable for use in a biological setting. Here, we explore the utility of this reaction for the synthesis of glutathione-S-conjugates (GSX) and present a general, operationally simple, protocol with a wide substrate scope. The GSX afforded are an important class of compounds and provide invaluable molecular tools to study glutathione-binding proteins. In this study we apply the diverse library of GSX synthesised to further our understanding of the structural requirements for binding to the glutathione-binding protein, Kef, a bacterial K(+) efflux system, found in many bacterial pathogens. This system is vital to the survival of bacteria upon exposure to electrophiles, and plays an essential role in the maintenance of intracellular pH and K(+) homeostasis. Consequently, Kef is an appealing target for the development of novel antibacterial drugs.
|Number of pages||8|
|Journal||Organic chemistry frontiers : an international journal of organic chemistry / Royal Society of Chemistry|
|Early online date||15 Feb 2016|
|Publication status||Published - 1 Apr 2016|
This work was funded by The Wellcome Trust (WT092552MA) and the Oxford University Press John Fell fund (093/380). SJC thanks St Hugh’s College, Oxford, for research support.
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- School of Medicine, Medical Sciences & Nutrition, Medical Sciences - Senior Lecturer
- School of Medicine, Medical Sciences & Nutrition, Microbiology and Immunity
- School of Medicine, Medical Sciences & Nutrition, Institute of Medical Sciences
Person: Academic Related - Scholarship, Academic