496808-47-0Relevant academic research and scientific papers
Metabolically stabilized derivatives of phosphatidylinositol 4-phosphate: Synthesis and applications
He, Ju,Gajewiak, Joanna,Scott, Jordan L.,Gong, Denghuang,Ali, Muzaffar,Best, Michael D.,Prestwich, Glenn D.,Stahelin, Robert V.,Kutateladze, Tatiana G.
scheme or table, p. 1312 - 1319 (2012/02/04)
Phosphatidylinositol 4-phosphate (PtdIns(4)P) lipid is an essential component of eukaryotic membranes and a marker of the Golgi complex. Here, we developed metabolically stabilized (ms) analogs of PtdIns(4)P and the inositol 1,4-bisphosphate (IP2) head group derivative and demonstrated that these compounds can substitute the natural lipid fully retaining its physiological activities. The methylenephosphonate (MP) and phosphorothioate (PT) analogs of PtdIns(4)P and the aminohexyl (AH)-IP2 probe are recognized by the PtdIns(4)P-specific PH domain of four phosphate adaptor protein 1 (FAPP1). Binding of FAPP1 to the PtdIns(4)P derivatives stimulates insertion of the PH domain into the lipid layers and induces tubulation of membranes. Both ms analogs and IP2 probes could be invaluable for identifying protein effectors and characterizing PtdIns(4)P-dependent signaling cascades within the trans-Golgi network (TGN).
Comprehensive and uniform synthesis of all naturally occurring phosphorylated phosphatidylinositols
Kubiak, Robert J.,Bruzik, Karol S.
, p. 960 - 968 (2007/10/03)
Studies of cellular signal transduction mechanisms involving receptor-mediated generation of inositol phosphates and phosphorylated phosphatidylinositols require easy access to these naturally occurring products. Although numerous synthetic methods have been developed during the past decade, most of these methods suffer from excessive length and lack of generality. In this work we describe the comprehensive and uniform synthesis of all naturally occurring phosphatidylinositols such as phosphatidylinositol, phosphatidylinositol 3-phosphate, 4-phosphate, 5-phosphate, 3,4-bisphosphate, 3,5-bisphosphate, 4,5-bisphosphate, and 3,4,5-trisphosphate, featuring both saturated and unsaturated fatty acid chains.
