Cantley, Alexandra MasuWoznica, ArielleBeemelmanns, ChristineKing, NicoleClardy, Jon2016-10-112016Cantley, Alexandra M., Arielle Woznica, Christine Beemelmanns, Nicole King, and Jon Clardy. 2016. “Isolation and Synthesis of a Bacterially Produced Inhibitor of Rosette Development in Choanoflagellates.” Journal of the American Chemical Society 138 (13): 4326-4329. doi:10.1021/jacs.6b01190. http://dx.doi.org/10.1021/jacs.6b01190.0002-7863http://nrs.harvard.edu/urn-3:HUL.InstRepos:29002628The 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.en-USJournal Article2016-10-1110.1021/jacs.6b01190