%0 Journal Article %A Cantley, Alexandra M. %A Woznica, Arielle %A Beemelmanns, Christine %A King, Nicole %A Clardy, Jon %D 2016 %T Isolation and Synthesis of a Bacterially Produced Inhibitor of Rosette Development in Choanoflagellates %U https://acs.figshare.com/articles/journal_contribution/Isolation_and_Synthesis_of_a_Bacterially_Produced_Inhibitor_of_Rosette_Development_in_Choanoflagellates/3123592 %R 10.1021/jacs.6b01190.s001 %2 https://acs.figshare.com/ndownloader/files/4859110 %K chemical ecology %K f r osettes %K bacterially %K multicellular states %K stereoisomer %K unicellular %K specificity %K laboratory %K choanoflagellate Salpingoeca rosetta %K i nhibitor %K Rosette Development %K Choanoflagellate %K IOR %K rosettes %K identification %K Bacterially Produced Inhibitor %K Synthesi %K multicellularity %K Isolation %K bacteria %K molecule %K understanding %K probe template %K sulfonolipid %K emergence %K marine eukaryote %K potency %K animal lineage %K model %K synthesis %K organism %X 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. %I ACS Publications