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Azide‐Modified Nucleosides as Versatile Tools for Bioorthogonal Labeling and Functionalization

Frederik Müggenburg, Sabine Müller

2022The Chemical Record27 citationsDOIOpen Access PDF

Abstract

Azide-modified nucleosides are important building blocks for RNA and DNA functionalization by click chemistry based on azide-alkyne cycloaddition. This has put demand on synthetic chemistry to develop approaches for the preparation of azide-modified nucleoside derivatives. We review here the available methods for the synthesis of various nucleosides decorated with azido groups at the sugar residue or nucleobase, their incorporation into oligonucleotides and cellular RNAs, and their application in azide-alkyne cycloadditions for labelling and functionalization.

Topics & Concepts

Bioorthogonal chemistryAzideSurface modificationClick chemistryChemistryCombinatorial chemistryNucleobaseCycloadditionAlkyneOligonucleotideNucleosideBioconjugationOrganic chemistryDNABiochemistryCatalysisPhysical chemistryClick Chemistry and ApplicationsAdvanced biosensing and bioanalysis techniquesChemical Synthesis and Analysis