Quorum sensing is the primary form of chemical communication in bacteria and is dependent upon the population density of the bacteria. The bacterium of interest is Lactobacillus plantarum, a commensal gram-positive bacterium. The quorum sensing circuit of this bacterium is regulated by the five amino acid peptide LamD. The native chemical structure of LamD is cyclic in the form of a thiolactone. Literature currently recognizes LamD as a thioester and we hypothesized there would be potential for the cyclization to proceed through an S to N acyl shift to a lactam. To test this hypothesis, two different methods utilizing solid phase peptide synthesis were used to synthesize linear LamD. The two linear LamD peptides were cyclized and analyzed for the lactam linkage. In the future, biological assays will be used to test the structure activity relationship between lactam derivatives of LamD and Lactobacillus plantarum.

Synthesis of lactam derivatives of LamD, a cyclic signaling peptide of Lactobacillus plantarum

256th National Meeting (2018)

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