An Entry of the Chemoselective Sulfo-Click Reaction into the Sphere of Nucleic Acids

Guillaume Clavé (1) , Enes Dursun , Jean-Jacques Vasseur (1) , Michael Smietana (1)

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

We report here the first example of a sulfo-click conjugation reaction to be applied to modified nucleosides. The reaction, which proceeds rapidly (k similar to 2.0 x 10(-1) M-1 s(-1) at 25 degrees C) under aqueous biocompatible conditions in the ribo- and deoxyribonucleoside series, affords the corresponding conjugated products in excellent yields. Furthermore, we demonstrate the orthogonality of the reaction with the copper-catalyzed azide-alkyne click reaction (CuAAC) by performing a one-pot dual labeling of a nucleoside carrying two orthogonal azido groups.

Mots clés: DNA; CHEMISTRY; BIOCONJUGATION; TECHNOLOGY; MOLECULES; THIOACIDS; MECHANISM; LIGATION; ANALOGS; CELLS

Domaines: Chimie analytique; Chimie thérapeutique; Chimie organique; Chimie

Guillaume Clavé, Enes Dursun, Jean-Jacques Vasseur, Michael Smietana. An Entry of the Chemoselective Sulfo-Click Reaction into the Sphere of Nucleic Acids. Organic Letters, 2020, 22 (5), pp.1914-1918. ⟨10.1021/acs.orglett.0c00265⟩. ⟨hal-02904428⟩