10015-87-9Relevant academic research and scientific papers
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.
Structural characterization of oxidized glycerophosphatidylserine: Evidence of polar head Oxidation
Maciel, Elisabete,Da Silva, Raquel Nunes,Simoes, Claudia,Domingues, Pedro,Domingues, M. Rosario M.
experimental part, p. 1804 - 1814 (2012/05/20)
Non-oxidized phosphatidylserine (PS) is known to play a key role in apoptosis but there is considerable research evidence suggesting that oxidized PS also plays a role in this event, leading to the increasing interest in studying PS oxidative modifications. In this work, different PS (1-palmitoyl-2-linoleoyl-sn-glycero-3-phospho-L-serine (PLPS), 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-L-serine (POPS), and 1,2-dipalmitoyl-sn-glycero-3-phospho-L-serine (DPPS) were oxidized in vitro by hydroxyl radical, generated under Fenton reaction conditions, and the reactions were monitored by ESI-MS in negative mode. Oxidation products were then fractionated by thin layer chromatography (TLC) and characterized by tandem mass spectrometry (MS/MS). This approach allowed the identification of hydroxyl, peroxy, and keto derivatives due to oxidation of unsaturated fatty acyl chains. Oxidation products due to oxidation of serine polar head were also identified. These products, with lower molecular weight than the non-modified PS, were identified as [M - 29 - H]- (terminal acetic acid), [M - 30 - H] - (terminal acetamide), [M - 13 - H]- (terminal hydroperoxyacetaldehyde), and [M - 13 - H]- (terminal hydroxyacetaldehyde plus hydroxy fatty acyl chain). Phosphatidic acid was also formed in these conditions. These findings confirm the oxidation of the serine polar head induced by the hydroxyl radical. The identification of these modifications may be a valuable tool to evaluate phosphatidylserine alteration under physiopathologic conditions and also to help understand the biological role of phosphatidylserine oxidation in the apoptotic process and other biological functions. American Society for Mass Spectrometry, 2011.
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
