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CDP-Ethanolamine and CDP-Choline: one-pot synthesis and P NMR study
Authors:Salma Ghezal  Maggie S Thomasson  Isabelle Lefebvre-Tournier  Christian Périgaud  Megan A Macnaughtan  Béatrice Roy
Institution:1. UMR 5247 CNRS-UM1-UM2, Institut des Biomolécules Max Mousseron, Nucleosides and Phosphorylated Effectors Team, Université Montpellier 2, cc1705, Place E. Bataillon, 34095 Montpellier, France;2. Louisiana State University, Department of Chemistry, Baton Rouge, LA 70803, USA
Abstract:Herein we report a one-pot multi-step synthesis of the cofactors CDP-Ethanolamine and CDP-Choline starting from cytidine 5′-monophosphate and using commercially available and/or easily prepared reagents. While studying the 31P NMR spectrum of CDP-Ethanolamine, an unexpected characteristic for a pyrophosphate diester was observed as it showed a singlet or two doublets depending upon the pH. Therefore, further NMR studies were undertaken to investigate the pH dependence of the peak splitting pattern and measure the acid dissociation constants of the compounds.
Keywords:CDP-Ethanolamine  CDP-Choline  Pyrophosphate diesters  Phosphorylation  31P NMR
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