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

Nicolas Probst; Rémy Lartia; Océane Théry; Mouâd Alami; Eric Defrancq; Samir Messaoudi

doi:10.1002/chem.201705371

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

Chemistry. 2018 Feb 6;24(8):1795-1800. doi: 10.1002/chem.201705371. Epub 2018 Jan 16.

Authors

Nicolas Probst¹, Rémy Lartia², Océane Théry², Mouâd Alami¹, Eric Defrancq², Samir Messaoudi¹

Affiliations

¹ BioCIS, Univ. Paris-Sud, CNRS, University Paris-Saclay, 92290, Châtenay-Malabry, France.
² University Grenoble-Alpes, DCM, CS 40700, 38058, Grenoble, France.

PMID: 29205564
DOI: 10.1002/chem.201705371

Abstract

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.

Keywords: DNA-glycoconjugates; Pd catalysis; oligonucleotides; thioglycoconjugation; thiosaccharide.

MeSH terms

Catalysis
Chromatography, High Pressure Liquid
Glycosylation
Oligonucleotides / chemistry*
Palladium / chemistry
Spectrometry, Mass, Electrospray Ionization
Sulfhydryl Compounds / chemistry*

Substances

Oligonucleotides
Sulfhydryl Compounds
Palladium