10015-87-9Relevant articles and documents
Efficient synthesis of phospholipids from glycidyl phosphates
Lindberg, Jan,Ekeroth, Johan,Konradsson, Peter
, p. 194 - 199 (2002)
New efficient routes to enantiopure phospholipids, starting from (S)-glycidol, are described. Lysophosphatidic acids and phosphatidic acids were obtained in good overall yields from (S)-glycidol, in only three and four steps, respectively. Moreover, the strategy can also be used to produce phosphatidylcholines in three steps. Using dialkylphosphoramidites, (S)-glycidol was phosphorylated to give (R)-1-O-glycidyl dialkyl phosphates. Regiospecific epoxide opening, using hexadecanol or cesium palmitate, followed by phosphate deprotection, provided lysophosphatidic acids. 2-O-Esterification prior to phosphate deprotection provided 1,2-O-diacyl and 1-O-alkyl-2-O-acyl phosphatidic acids. Phosphorylation of (S)-glycidol using phosphorus oxychloride followed by in situ treatment with choline tosylate produced (R)-glycidyl phosphocholine. Subsequent nucleophilic opening of the epoxide using cesium palmitate produced 1-O palmitoyl-sn-glycero-3-phosphocholine, which has been used in syntheses of phosphatidylcholines.
Liposome-Mediated Enzymatic Synthesis of Phosphatidylcholine as an Approach to Self-Replicating Liposomes
Schmidli, Peter Kurt,Schurtenberger, Peter,Luisi, Pier Luigi
, p. 8127 - 8130 (2007/10/02)
The four enzymes of the salvage pathway for phosphatidylcholine synthesis sn-glycerol-3-phosphate acyltransferase, 1-acyl-sn-glycerol-3-phosphate acyltransferase, phosphatidate phosphatase, and cytidinediphosphocholine phosphocholinetransferase were simul
