Biomaterial Database

Synthesis of unsaturated phosphatidylinositol 4,5-bisphosphate and analogues. 2009

Nitesh Panchal, and Piers R J Gaffney

Department of Chemistry, Imperial College, Exhibition Road, London, UK SW7 2AZ.

A new approach for the synthesis of phosphatidylinositol 4,5-bisphosphate [PtdIns(4,5)P2] is described, compatible with unsaturated fatty acid esters, as well as phosphorothioate and acetylenic analogues. This strategy depends on masking the phosphate charges with base-labile cyanoethyl esters, and the hydroxyls of the target with mild acid-labile protecting groups. A two-step basic then acidic global unblocking of orthogonal protecting groups provides the target lipid. A xanthenylidene acetal was used for key temporary protection of the 4,5-diol, and the 6-O was protected with a 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl (Cpep) acetal.

UI	MeSH Term	Description	Entries
D008968	Molecular Conformation	The characteristic three-dimensional shape of a molecule.	Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D018129	Phosphatidylinositol Phosphates	Phosphatidylinositols in which one or more alcohol group of the inositol has been substituted with a phosphate group.	Polyphosphoinositides,Phosphatidyl Inositol Phosphates,Polyphosphoinositide,Inositol Phosphates, Phosphatidyl,Phosphates, Phosphatidyl Inositol,Phosphates, Phosphatidylinositol
D019269	Phosphatidylinositol 4,5-Diphosphate	A phosphoinositide present in all eukaryotic cells, particularly in the plasma membrane. It is the major substrate for receptor-stimulated phosphoinositidase C, with the consequent formation of inositol 1,4,5-triphosphate and diacylglycerol, and probably also for receptor-stimulated inositol phospholipid 3-kinase. (Kendrew, The Encyclopedia of Molecular Biology, 1994)	PtdInsP2,Phosphatidylinositol 4,5-Biphosphate,Phosphatidylinositol Phosphate, PtdIns(4,5)P2,Phosphatidylinositol-4,5-Biphosphate,PtIns 4,5-P2,PtdIns(4,5)P2,PtdInsP,4,5-Biphosphate, Phosphatidylinositol,4,5-Diphosphate, Phosphatidylinositol,Phosphatidylinositol 4,5 Biphosphate,Phosphatidylinositol 4,5 Diphosphate