Synthesis of the Rosette-Inducing Factor RIF-1 and Analogs

Citations Over TimeTop 10% of 2014 papers

Abstract

Studies on the origin of animal multicellularity have increasingly focused on one of the closest living relatives of animals, the choanoflagellate Salpingoeca rosetta. Single cells of S. rosetta can develop into multicellular rosette-shaped colonies through a process of incomplete cytokinesis. Unexpectedly, the initiation of rosette development requires bacterially produced small molecules. Previously, our laboratories reported the planar structure and femtomolar rosette-inducing activity of one rosette-inducing small molecule, dubbed rosette-inducing factor 1 (RIF-1), produced by the Gram-negative Bacteroidetes bacterium Algoriphagus machipongonensis. RIF-1 belongs to the small and poorly explored class of sulfonolipids. Here, we report a modular total synthesis of RIF-1 stereoisomers and structural analogs. Rosette-induction assays using synthetic RIF-1 stereoisomers and naturally occurring analogs defined the absolute stereochemistry of RIF-1 and revealed a remarkably restrictive set of structural requirements for inducing rosette development.

Related Papers

• → Spontaneous rosette formation of carp peripheral leucocytes with mammalian red blood cells.(1990)4 cited
• → EVALUATION OF ANTIHUMAN ANTILYMPHOCYTE SERUM WITH THE ROSETTE INHIBITION TEST USING HUMAN AND CYNOMOLGUS THYMOCYTES(1972)3 cited
• → Differentiating Owl Monkey T and B Lymphocytes byRosette Formation(1980)3 cited
• [The characteristics of e-rosette forming cells in cancer patients, especially in heat stable E-rosette (HSE-rosette) formation and e-rosette inhibition by antilymphocyte serum (ALS) (author's transl)].(1980)
• [The effect of gamma irradiation on the direct intercellular interaction (rosette formation) of thymic macrophages with thymocytes].(1992)