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.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1002/chem.201705371 | DOI Listing |
Chemistry
December 2024
Univ. Lille, CNRS, UMR, 8576 - UGSF - Unité de Glycobiologie Structurale et Fonctionnelle, Lille, France.
Lignin biosynthesis is a critical process that underpins plant structural integrity and defenses. Central to this pathway are monolignol glucosides (MLGs), whose role as intermediates remains debated. To elucidate MLGs' involvement, we developed thioglycosylated monolignol probes compatible with click chemistry for in situ visualization of lignin biosynthesis.
View Article and Find Full Text PDFMolecules
February 2018
BioCIS, Université Paris-Sud, CNRS, University Paris-Saclay, Châtenay-Malabry 92296, France.
Buchwald-Hartwig-Migita cross-coupling of 1-thiosugars with α- or β-3-iodo-N-glycosylquinolin-2-ones has been accomplished under mild and operationally simple reaction conditions through the use of a Pd-G3 XantPhos palladacycle precatalyst. This new methodology has been successfully applied to a variety of α- or β-mono-, di-, and poly-thiosugar derivatives to efficiently synthesize a series of α- or β-N,S-bis-glycosyl quinolin-2-ones, which are difficult to synthesize by classical methods.
View Article and Find Full Text PDFChemistry
February 2018
BioCIS, Univ. Paris-Sud, CNRS, University Paris-Saclay, 92290, Châtenay-Malabry, France.
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.
View Article and Find Full Text PDFJ Org Chem
July 2017
Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, University of Paris-Sud, CNRS, BioCIS-UMR 8076 , 5 rue J.-B. Clément, Châtenay-Malabry F-92296, France.
Buchwald-Hartwig-Migita cross-coupling of 1-thiosugars with 2-iodoglycals has been accomplished under mild and operationally simple reaction conditions through the use of Pd-G3 XantPhos palladacycle precatalyst. This new methodology has been successfully applied to a variety of α- or β-mono-, di-, and polythiosugar derivatives to synthesize efficiently a series of (1 → 2)-S-linked thiosaccharides and S-linked glycoconjugates, which are difficult to synthesize by classical methods.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!