Synthesis of 9-Dechlorochrysophaentin A Enables Studies Revealing Bacterial Cell Wall Biosynthesis Inhibition Phenotype in B. subtilis.
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ABSTRACT:
SUBMITTER: Fullenkamp CR
PROVIDER: S-EPMC7771388 | biostudies-literature | 2020 Sep
REPOSITORIES: biostudies-literature
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Synthesis of 9-Dechlorochrysophaentin A Enables Studies Revealing Bacterial Cell Wall Biosynthesis Inhibition Phenotype in <i>B. subtilis</i>.
Fullenkamp Christopher R CR Hsu Yen-Pang YP Quardokus Ellen M EM Zhao Gengxiang G Bewley Carole A CA VanNieuwenhze Michael M Sulikowski Gary A GA
Journal of the American Chemical Society 20200908 38
Chrysophaentin A is an antimicrobial natural product isolated from the marine alga <i>C. taylori</i> 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 <i>Z</i>-selective ring-closing metathesis (RCM) cyclization followed by an oxygen to carbon ring contraction is described. Fluorescent microscopy studies revealed 9-d ...[more]
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