CDP-Ethanolamine and CDP-Choline: one-pot synthesis and 31P NMR study.

Salma Ghezal (1) , Maggie S. Thomasson (2) , Isabelle Lefebvre-Tournier (1) , Christian Perigaud (1) , Megan A. Macnaughtan (2) , Béatrice Roy (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]
2 Department of Chemistry

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.

Mots clés: CDP-Ethanolamine; CDP-Choline; Pyrophosphate diesters; Phosphorylation; 31P NMR

Domaines: Chimie organique

Salma Ghezal, Maggie S. Thomasson, Isabelle Lefebvre-Tournier, Christian Perigaud, Megan A. Macnaughtan, et al.. CDP-Ethanolamine and CDP-Choline: one-pot synthesis and 31P NMR study.. Tetrahedron Letters, 2014, 55 (38), pp.5306-5310. ⟨10.1016/j.tetlet.2014.07.076⟩. ⟨hal-01061599⟩