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Diverted Total Synthesis of Carolacton-Inspired Analogs Yields Three Distinct Phenotypes in Streptococcus mutans Biofilms.


ABSTRACT: The oral microbiome is a dynamic environment inhabited by both commensals and pathogens. Among these is Streptococcus mutans, the causative agent of dental caries, the most prevalent childhood disease. Carolacton has remarkably specific activity against S. mutans, causing acid-mediated cell death during biofilm formation; however, its complex structure limits its utility. Herein, we report the diverted total synthesis and biological evaluation of a rationally designed library of simplified analogs that unveiled three unique biofilm phenotypes further validating the role of natural product synthesis in the discovery of new biological phenomena.

SUBMITTER: Solinski AE 

PROVIDER: S-EPMC5891724 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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Diverted Total Synthesis of Carolacton-Inspired Analogs Yields Three Distinct Phenotypes in Streptococcus mutans Biofilms.

Solinski Amy E AE   Koval Alexander B AB   Brzozowski Richard S RS   Morrison Kelly R KR   Fraboni Americo J AJ   Carson Carrie E CE   Eshraghi Anisa R AR   Zhou Guangfeng G   Quivey Robert G RG   Voelz Vincent A VA   Buttaro Bettina A BA   Wuest William M WM  

Journal of the American Chemical Society 20170517 21


The oral microbiome is a dynamic environment inhabited by both commensals and pathogens. Among these is Streptococcus mutans, the causative agent of dental caries, the most prevalent childhood disease. Carolacton has remarkably specific activity against S. mutans, causing acid-mediated cell death during biofilm formation; however, its complex structure limits its utility. Herein, we report the diverted total synthesis and biological evaluation of a rationally designed library of simplified analo  ...[more]

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