84062-61-3Relevant academic research and scientific papers
Discrimination of chain positions in mixed short/long-chain glycerophosphocholines by NMR chemical shift variations
D'Arrigo, Paola,Mele, Andrea,Rossi, Cristina,Tessaro, Davide,Servi, Stefano
experimental part, p. 1005 - 1011 (2009/12/03)
The synthesis of a series of (1,2-) mixed short/long-chain glycerophosphocholines has been performed. Starting from glycerophosphorylcholine (GPC), and using regioselective acylation in the presence of dibutyltin oxide, a set of high-purity isomeric mixed-chain phospholipids was obtained. This has allowed the development of a simple NMR method for the structural determination of the isomeric 1(2)-short-2(1)-long- diacylglycerophosphocholines. The method is based on the observation that selected protons in the two series of isomeric phospholipids undergo systematic chemical shift variations Δδ that can be ascribed to the acyl substituents on the glycerol backbone. The observed patterns can be exploited as a simple method for the discrimination of regioisomeric unsymmetrical 1,2-diacylglycerophosphocholines.
A practical selective synthesis of mixed short/long chains glycerophosphocholines
D'Arrigo, Paola,Fasoli, Ezio,Pedrocchi-Fantoni, Giuseppe,Rossi, Cristina,Saraceno, Caterina,Tessaro, Davide,Servi, Stefano
, p. 113 - 118 (2008/02/04)
Glycerophosphorylcholine (GPC) is transformed into the cyclic stannylene derivatives, which are selectively acylated to 1-acyl-2-lyso-glycerophosphocholines. The reaction is effective using C-2 to C-16 acid chlorides in 2-propanol. After solvent replacement the lyso-phospholipid (lyso-PL) is subjected to a second acylation using acid anhydrides in methylene chloride. A series of 1(2)-short-2(1)-long-diacyl-glycerophosphocholines are obtained in high yields and selectivity. No diacylation product was detected. In order to detect mixed-chain lipids with inverted disposition of acyl chains, the long chain was introduced first and the thus resulting isomeric compounds compared by NMR. An NMR method was developed in order to determine the positional purity of the isomeric compounds.
Derivatives of glycerophosphocholine and glycerophosphoethanolamine, their preparation and their use
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, (2008/06/13)
The invention relates to new triphenylmethyl derivatives of sn-glycero-3-phosphocholine and sn-glycero-3-phosphoethanolamine of the general formula STR1 in which T denotes a triphenylmethyl group which is unsubstituted or monosubstituted or polysubstitute
