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J Am Chem Soc. 2016 Apr 6;138(13):4326-9. doi: 10.1021/jacs.6b01190. Epub 2016 Mar 24.

Isolation and Synthesis of a Bacterially Produced Inhibitor of Rosette Development in Choanoflagellates.

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Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School , 240 Longwood Avenue, Boston, Massachusetts 02115, United States.
Howard Hughes Medical Institute and Department of Molecular and Cell Biology, University of California , Berkeley, California 94720, United States.
Leibniz Institute for Natural Product Research and Infection Biology e.V., Hans-Knöll Institute (HKI) , Beutenbergstrasse 11a, 07745 Jena, Germany.


The choanoflagellate Salpingoeca rosetta is a microbial marine eukaryote that can switch between unicellular and multicellular states. As one of the closest living relatives of animals, this organism has become a model for understanding how multicellularity evolved in the animal lineage. Previously our laboratories isolated and synthesized a bacterially produced sulfonolipid that induces S. rosetta to form multicellular "rosettes." In this study, we report the identification of a bacterially produced inhibitor of rosettes (IOR-1) as well as the total synthesis of this molecule and all of its stereoisomers. Our results confirm the previously noted specificity and potency of rosette-modulating molecules, expand our understanding of the complex chemical ecology between choanoflagellates and rosette-inducing bacteria, and provide a synthetic probe template for conducting further mechanistic studies on the emergence of multicellularity.

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