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J Am Chem Soc. 2017 May 31;139(21):7188-7191. doi: 10.1021/jacs.7b03879. Epub 2017 May 17.

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

Author information

1
Department of Chemistry, Temple University , Philadelphia, Pennsylvania 19122, United States.
2
Center for Oral Biology, University of Rochester School of Medicine and Dentistry , Rochester New York 14642, United States.
3
Department of Microbiology and Immunology, Lewis Katz School of Medicine, Temple University , Philadelphia, Pennsylvania 19140, United States.

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.

PMID:
28502178
PMCID:
PMC5891724
DOI:
10.1021/jacs.7b03879
[Indexed for MEDLINE]
Free PMC Article

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