The ability to incorporate bio-orthogonal carbohydrate probes, specifically, 2-azido and 2-alkyne muramic acid, into bacterial peptidoglycan (PGN) backbone has proven useful in studying the structural morphology of this essential polymer as well as tracking the natural, immunostimulatory fragments generated from this protective muropeptide polymer. The innate immune system’s response to bacteria that normally populate the human body has been connected to mutations of the nucleotide-binding oligomerization domain-containing protein 2 (NOD2) and the binding to these PGN fragments. Several species-specific variations of PGN fragments have been shown to bind and activate NOD2, but primarily the synthetic fragment muramyl dipeptide (MDP) is used as a standard for assessing immune activation. Therefore, to understand the breakdown process and signaling at the molecular level, it is essential to have a method to identify these fragments and study the mechanism to this molecular interaction. To further investigate and allow for in vivo tracking of bacteria cell wall fragments, we prepare a new suite of fluorine-containing N-acetyl muramic acid (NAM) fragments via a shortened synthesis, which features a carboxybenzyl (Cbz) protecting group at the 2N-position. Fluorine-containing probes offer several advantages over the previously used fluorescent probes. In addition to fluorine’s low natural occurrence in biological systems and heightened sensitivity to nuclear magnetic resonance (NMR), the range of fluorine chemical shifts to the details of the local environment are much greater than that of hydrogen. The synthesis of several fluorine-containing NAM derivatives allows for the development of a new series of probes that allow for the in vivo detection of PG fragments in relation with the innate immune system.

Synthesis of fluorine-containing N-acetyl muramic acid derivatives for in vivo imaging of metabolically labelled bacterial peptidoglycan

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.