150577-01-8Relevant academic research and scientific papers
Total synthesis of a glycosylphosphatidylinositol anchor of the human lymphocyte CD52 antigen
Burgula, Srinivas,Swarts, Benjamin M.,Guo, Zhongwu
, p. 1194 - 1201 (2012/03/26)
The first total synthesis of a glycosylphosphatidylinositol (GPI) anchor bearing a polyunsaturated arachidonoyl fatty acid is reported. This lipid is found in mammalian GPIs that do not undergo lipid remodeling, a process that has important implications in the localization and function of GPI-anchored proteins. Incorporation of the oxidation- and reduction-sensitive arachidonoyl lipid in the target GPI was accomplished by using the para-methoxybenzyl (PMB) group for permanent hydroxyl group protection, which featured a selective, rapid, and efficient global deprotection protocol. The flexibility of this synthetic strategy was further highlighted by the inclusion of two additional GPI core structural modifications present in the GPI anchor of the human lymphocyte CD52 antigen. Lipid diversity in GPI synthesis: The convergent synthesis of an arachidonoyl-containing glycosylphosphatidylinositol (GPI) anchor of the human lymphocyte CD52 antigen is reported. Incorporation of the oxidation- and reduction-sensitive polyunsaturated arachidonoyl lipid, as well as two additional GPI core modifications (see structure), was enabled by using a para-methoxybenzyl (PMB)-based global protection strategy. Copyright
Synthesis of naturally occurring phosphatidylinositol 3,4,5-trisphosphate [PtdIns(3,4,5)P3] and its diastereoisomers
Gaffney, Piers R.J.,Reese, Colin B.
, p. 192 - 205 (2007/10/03)
The chemical synthesis of naturally occurring phosphatidylinositol 3,4,5-triphosphate [PtdIns(3,4,5)P3] and its diastereoisomers was discussed. In the first stage, the preparation of the required enantiomeric 1,2-di-O-acylglycerol derivatives was done. The second stage involved the preparation of suitably protected enantiomeric myo-inositol 1-phosphates. The glycerol and inositol building blocks were coupled together and the 3-, 4- and 5-hydroxy functions of the inositol residues in the coupled products were phosphorylated. Finally, the protecting groups were removed to give PtdIns(3,4,5)P3 and its diastereoisomers.
Preparation of 2-O-arachidonoyl-1-O-stearoyl-sn-glycerol and other di-O-acyl glycerol derivatives
Gaffney, Piers R.J.,Reese, Colin B.
, p. 2539 - 2542 (2007/10/03)
R(-)-2,3- and S(+)-1,2-O-Isopropylidene-sn-glycerols (4 and 9) are converted into 2-O-arachidonoyl-1-O-stearoyl and 2-O-arachidonoyl-3-O-stearoyl-sn-glycerols (2 and 3, respectively); glycerol is also converted into its racemic 1,2- and its symmetrical 13-di-O-linoleoyl derivatives (14 and 17, respectively).
