<a href="https://departments.bryant.edu/science-and-technology/faculty/reid-christopher"><img src="https://departments.bryant.edu/sites/departments/files/2019-04/faculty-cas-science-technology-reid-460x460.jpg" alt="Christopher Reid" align="right" margin="10px" width="200px"></a>
Synthesis of Masarimycin, a Small Molecule Inhibitor of Gram-Positive Bacterial Growth
Authors: Christopher Reid
<br> Peptidoglycan (PG) in the cell wall of bacteria is a unique macromolecular structure that confers shape, and protection from the surrounding environment. Central to understanding cell growth and division is the knowledge of how PG degradation influences biosynthesis and cell wall assembly. Recently, the metabolic labeling of PG through the introduction of modified sugars or amino acids has been reported. While chemical interrogation of biosynthetic steps with small molecule inhibitors is possible, chemical biology tools to study PG degradation by autolysins are underdeveloped. Bacterial autolysins are a broad class of enzymes that are involved in the tightly coordinated degradation of PG. Here, a detailed protocol is presented for preparing a small molecule probe, masarimycin, which is an inhibitor of N-acetylglucosaminidase LytG in
Bacillus subtilis,
and cell wall metabolism in
Streptococcus pneumoniae
. Preparation of the inhibitor
via
microwave-assisted and classical organic synthesis is provided. Its applicability as a tool to study Gram-positive physiology in biological assays is presented.