Insights into the Soluble PEG-Supported Synthesis of Cytosine-Containing Nucleoside 5′-Mono-, Di-, and Triphosphates

Céline Crauste (1) , Christian Périgaud (1) , Suzanne Peyrottes (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]

Nucleoside phosphoesters (nucleotides) have crucial roles in a large variety of biological processes including nucleic acid biosynthesis and their corresponding analogues are extensively used as biological tools. Herein, we describe a new and efficient synthetic procedure involving polyethylene glycol (PEG) as soluble support and regioselective mono-, di-, and triphosphorylation steps. Applied to natural and synthetic cytosine containing nucleosides, this methodology allowed the preparation of various phosphorylated forms in high yields and good purity.

Domaines: Chimie organique; Chimie thérapeutique

Céline Crauste, Christian Périgaud, Suzanne Peyrottes. Insights into the Soluble PEG-Supported Synthesis of Cytosine-Containing Nucleoside 5′-Mono-, Di-, and Triphosphates. Journal of Organic Chemistry, 2009, 74 (23), pp.9165-9172. ⟨10.1021/jo901931z⟩. ⟨hal-02309892⟩