<br/>Quorum sensing is a bacterial signaling system that involves the synthesis, secretion, and detection of small signal molecules called autoinducers. One main class of autoinducers in Gram negative bacteria are acylated homoserine lactones (AHLs), which are made by the LuxI family of AHL synthases and detected by the LuxR family of autoinducer receptors. Autoinducer signaling through LuxR alters the transcription of genes regulated by quorum sensing, which include virulence genes in some species that are human pathogens. Our lab aims to synthesize inhibitors of the autoinducer synthase enzyme in order to block the production of autoinducers and thus preventing expression of virulence genes controlled by quorum sensing. Here we describe our progress towards the efficient preparation of natural and synthetic acyl donor substrates for AHL synthase enzymes to support an in vitro enzymatic assay. First, we describe an efficient synthesis of acyl-ACP, the natural AHL synthase substrate. We chemically acylate CoA and use the resulting acyl CoA as a substrate for enzymatic transfer of its acyl pantetheine group to acyl carrier protein (ACP) to make acyl-ACP. We also describe the synthesis and evaluation of acyl-pantetheine and acyl phosphopantetheine as synthetic acyl donor substrates for AHL synthase enzymes.

Efficient preparation of natural and synthetic acyl donor substrates for quorum sensing autoinducer synthase enzymes

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.