Bacteria are surrounded by peptidoglycan (PG), a glycopeptide polymer composed of alternating units of N-acetyl glucosamine (NAG) and N-acetyl muramic acid (NAM), which contains a pentapeptide chain off the 3 position which can be further crosslinked across strands. The PG cell wall is important in determining cell shape, serving as a scaffold for other envelope structures, and protecting bacteria from osmotic lysis. Across Gram-positive and Gram-negative bacteria, PG biosynthesis is highly conserved. With the rise of antibiotic resistant microbial strains and the fact humans do not synthesize PG, this biosynthetic pathway is an ideal target for antibiotic development. We are expanding our current library of NAM derivatives to include a variety of functional groups such as fluorophores and bio-orthogonal handles to better understand the enzymatic machinery of PG biogenesis. Herein, we report a library of new NAM derivatives to use in metabolic labeling experiments. All derivatives were assessed as substrates for the PG biosynthetic pathway by mass spectrometry analysis of in vitro reactions using the substrate alongside the purified bacterial cell wall biosynthetic/recycling enzymes and through cell survival assays. These probes will prove extremely useful in understanding the biochemistry of bacterial cell wall biosynthesis and overall peptidoglycan architecture.

Expanding the library of N-acetyl muramic acid derivatives: Probing the peptidoglycan biogenesis machinery

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.