Synthesis of 9-Dechlorochrysophaentin A Enables Studies Revealing Bacterial Cell Wall Biosynthesis Inhibition Phenotype in B. subtilis .

Autor:	Fullenkamp CR; Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, United States., Hsu YP; Department of Chemistry, Indiana University, Bloomington, Indiana 47405, United States.; Department of Molecular and Cellular Biochemistry, Indiana University, Bloomington, Indiana 47405, United States., Quardokus EM; Department of Chemistry, Indiana University, Bloomington, Indiana 47405, United States., Zhao G; Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892, United States., Bewley CA; Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892, United States., VanNieuwenhze M; Department of Chemistry, Indiana University, Bloomington, Indiana 47405, United States.; Department of Molecular and Cellular Biochemistry, Indiana University, Bloomington, Indiana 47405, United States., Sulikowski GA; Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, United States.; Department of Pharmacology, Vanderbilt University, Nashville, Tennessee 37235, United States.; Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235, United States.
Jazyk:	angličtina
Zdroj:	Journal of the American Chemical Society [J Am Chem Soc] 2020 Sep 23; Vol. 142 (38), pp. 16161-16166. Date of Electronic Publication: 2020 Sep 08.
DOI:	10.1021/jacs.0c04917
Abstrakt:	Chrysophaentin A is an antimicrobial natural product isolated from the marine alga C. taylori in milligram quantity. Structurally, chrysophaentin A features a macrocyclic biaryl ether core incorporating two trisubstituted chloroalkenes at its periphery. A concise synthesis of iso- and 9-dechlorochrysophaentin A enabled by a Z -selective ring-closing metathesis (RCM) cyclization followed by an oxygen to carbon ring contraction is described. Fluorescent microscopy studies revealed 9-dechlorochrysophaentins leads to inhibition of bacterial cell wall biosynthesis by disassembly of key divisome proteins, the cornerstone to bacterial cell wall biosynthesis and division.
Databáze:	MEDLINE
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