The amount of antibiotic-resistant bacteria species has increased over the years, creating a dire need for the synthesis and study of new potential antibiotics. A possible solution lies in the methylerythritol phosphate (MEP) pathway. MEP is a bacterial pathway found in pathogenic species (e.g. Salmonella spp. and Mycobacterium tuberculosis), but not in animals and humans. One of the essentials for cell survival, isoprenoids, are produced in this pathway. Thus, the enzymes of the MEP pathway could act as a potential target for therapeutics. One of the isoprenoids produced in this pathway is a byproduct, 5-hydroxy-2,3-pentanedione (laurencione). The byproduct is highly similar in structure to the autoinducer-2 (AI-2) precursor, 4,5-dihydroxy-2,3-pentanedione (DPD). DPD is a molecule that is involved in bacterial quorum sensing, which is a form of bacterial communication. The similarity between these two structures could implicate that the laurencione also plays a certain role in the quorum sensing of bacteria. As such, the purpose of this study is to synthesize laurencione and its derivatives that are useful for its detection and quantification. In order to examine if 5-hydroxy-2,3-pentanedione acts similarly to DPD, it was tested on Vibrio harveyi MM30. Vibrio harveyi is a bacterial species that utilizes DPD to produce light. The mutant version of Vibrio harveyi is not capable of producing DPD. The results from this study showed that 5-hydroxy-2,3-pentanedione does influence the bioluminescence produced by the V. harveyi mutant. Other derivatives of 5-hydroxy-2,3-pentanedione were not synthesized in sufficient quantities to be analyzed.

Syntheses of laurencione and its derivatives: Is laurencione involved in bacterial communication?

255th National Meeting (2018)

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