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Discrimination of Chain Positions in Mixed Short/Long-Chain Glycerophosphocholines by NMR Chemical Shift Variations

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Journal of the American Oil Chemists' Society

Abstract

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.

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Authors and Affiliations

  1. Dipartimento di Chimica, Materiali e Ingegneria Chimica G. Natta, Politecnico di Milano, Via Mancinelli 7, 20131, Milan, Italy

    Paola D’Arrigo, Andrea Mele, Cristina Rossi, Davide Tessaro & Stefano Servi

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  1. Paola D’Arrigo
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  2. Andrea Mele
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  3. Cristina Rossi
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  4. Davide Tessaro
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  5. Stefano Servi
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Correspondence to Paola D’Arrigo.

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D’Arrigo, P., Mele, A., Rossi, C. et al. Discrimination of Chain Positions in Mixed Short/Long-Chain Glycerophosphocholines by NMR Chemical Shift Variations. J Am Oil Chem Soc 85, 1005–1011 (2008). https://doi.org/10.1007/s11746-008-1280-4

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  • DOI: https://doi.org/10.1007/s11746-008-1280-4

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