Efficient Buchwald-Hartwig-Migita Cross-Coupling for DNA Thioglycoconjugation

Nicolas Probst (1) , Rémy Lartia (2) , Océane Théry (3) , Mouad Alami (4) , Eric Defrancq (2) , Samir Messaoudi (1)

1 BioCIS - Biomolécules : Conception, Isolement, Synthèse
2 DCM - I2BM - Département de Chimie Moléculaire - Ingéniérie et Intéractions BioMoléculaires
3 DCM - Département de Chimie Moléculaire
4 MBCIS - Molécules bioactives, conception, isolement et synthèse

An efficient method for the thioglycoconjugation of iodinated oligonucleotides by Buchwald-Hartwig-Migita cross-coupling under mild conditions is reported. The method enables divergent synthesis of many different functionalized thioglycosylated ODNs in good yields, without affecting the integrity of the other A, C, and G nucleobases.

Mots clés: DNA-glycoconjugates; Pd catalysis; oligonucleotides; thioglycoconjugation; thiosaccharide

Domaines: Chimie thérapeutique

Nicolas Probst, Rémy Lartia, Océane Théry, Mouad Alami, Eric Defrancq, et al.. Efficient Buchwald-Hartwig-Migita Cross-Coupling for DNA Thioglycoconjugation. Chemistry - A European Journal, 2018, 24 (8), pp.1795-1800. ⟨10.1002/chem.201705371⟩. ⟨hal-01846958⟩