496808-72-1

Upstream product

• 496808-81-2 1D-5-O-benzoyl-1-(tert-butyldiphenylsilyl)-2,4,6-O-tris(methoxymethylene)-myo-inositol 
• 496921-95-0 C₁₆H₂₆O₆C₁₆H₁₈Si 
• 142534-54-1 1D-1-O-(tert-butyldiphenylsilyl)-myo-inositol 
• 331679-26-6 2,3-O-(D-1,7,7-trimethylbicyclo[2.2.1]hept-6-ylidene)-D-myo-inositol 
• 496808-71-0 Phosphoric acid dibenzyl ester (1S,2R,3R,4S,5R,6S)-3-(bis-benzyloxy-phosphoryloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2,4,6-tris-methoxymethoxy-cyclohexyl ester 

Downstream Products

• 496808-73-2 1D-O-(1,2-di-O-palmitoyl-sn-glycerol-3-O-methylphospho)-2,4,6-O-tris(methoxymethylene)-myo-inositol 3,5-bis(dibenzyl phosphate) 

Relevant academic research and scientific papers

Regioselective approach to phosphatidylinositol 3,5-bisphosphates: Syntheses of the native phospholipid and biotinylated short-chain derivative

Figure presented A selective bis-silylation of 1D-O-TBDPS-myo-inositol leads to a 1,3,5-trisubstituted inositol, which can be advanced to the headgroup of phosphatidylinositol-3,5-bisphosphate [PI(3,5)P2]. A mild, regioselective method for construction of the diacylglycerol moiety containing differing fatty acid chains, including the naturally occurring lipids, was developed. Their union in the synthesis of the cell-signaling molecule PI(3,5)P2 containing the sn-1-stearoyl and sn-2-arachidonoyl groups is described. The methodology was also used to generate dioctanoyl-PI(3,5)P 2 and a previously unreported biotin-PI(3,5)P2 conjugate, which was coupled to neutravidin beads and used to pull down PI(3,5)P 2-binding proteins from the cytosolic extract of adrenal neurosecretory cells. We report the specific pull-down of the PI(3,5)P 2-binding protein svp1p, a known PI(3,5)P2 effector involved in membrane trafficking.

Comprehensive and uniform synthesis of all naturally occurring phosphorylated phosphatidylinositols

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.