Academic Journal
Oligonucleotides Post-Synthetic Modifications: An Overview of Clickable Nucleoside Phosphoramidites Suitable for Solid-Phase Synthesis.
| Τίτλος: | Oligonucleotides Post-Synthetic Modifications: An Overview of Clickable Nucleoside Phosphoramidites Suitable for Solid-Phase Synthesis. |
|---|---|
| Συγγραφείς: | Depienne S; Université Paris-Saclay, CNRS, Institut de Chimie Moléculaire et des Matériaux d'Orsay, UMR CNRS 8182, Orsay, France., Bristiel A; Unité Drug Design Small Molecules, Institut de Recherche et Développement Servier Paris-Saclay, Gif-sur-Yvette, France., Urban D; Université Paris-Saclay, CNRS, Institut de Chimie Moléculaire et des Matériaux d'Orsay, UMR CNRS 8182, Orsay, France., Guianvarc'h D; Université Paris-Saclay, CNRS, Institut de Chimie Moléculaire et des Matériaux d'Orsay, UMR CNRS 8182, Orsay, France. |
| Πηγή: | Chembiochem : a European journal of chemical biology [Chembiochem] 2026 Jul 14; Vol. 27 (13), pp. e70347. |
| Τύπος έκδοσης: | Journal Article; Review; Research Support, Non-U.S. Gov't |
| Γλώσσα: | English |
| Στοιχεία περιοδικού: | Publisher: Wiley-VCH Verlag Country of Publication: Germany NLM ID: 100937360 Publication Model: Print Cited Medium: Internet ISSN: 1439-7633 (Electronic) Linking ISSN: 14394227 NLM ISO Abbreviation: Chembiochem Subsets: MEDLINE |
| Imprint Name(s): | Original Publication: Weinheim, Germany : Wiley-VCH Verlag, c2000- |
| Ιατρικοί όροι (MeSH): | Solid-Phase Synthesis Techniques*/methods , Oligonucleotides*/chemistry , Oligonucleotides*/chemical synthesis , Organophosphorus Compounds*/chemistry , Nucleosides*/chemistry , Click Chemistry*, Cycloaddition Reaction |
| Περίληψη: | Chemical modification of oligonucleotides has become an essential strategy to improve their properties and expand their functional utility in chemical biology, molecular imaging, and therapeutics. Among the various modification strategies, post-synthetic bioorthogonal click chemistry enables efficient, rapid, and biocompatible site-specific conjugation of functional moieties. Central to these advances is the development of clickable nucleoside phosphoramidites, namely nucleoside building blocks containing reactive bioorthogonal click handles that are compatible with the harsh conditions of solid-phase oligonucleotide synthesis (SPOS). This review provides a comprehensive overview of bioorthogonal cycloaddition-based nucleoside phosphoramidites reported to date that are compatible with SPOS. We highlight their synthetic accessibility and deviations from conventional SPOS protocols when required, as well as the stability and hybridization behavior of the resulting clickable oligonucleotides. Furthermore, we examine the performance of subsequent bioorthogonal reactions used for post-synthetic functionalization, with particular attention to their kinetics and efficiencies. Representative applications are also discussed, including the development of labeled probes, multifunctional assemblies, and targeted delivery systems. (© 2026 The Author(s). ChemBioChem published by Wiley‐VCH GmbH.) |
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| Contributed Indexing: | Keywords: bioorthogonal chemistry; click chemistry; oligonucleotides; post‐synthetic modification; solid‐phase oligonucleotides synthesis |
| Substance Nomenclature: | 0 (Oligonucleotides) 0 (Organophosphorus Compounds) 0 (phosphoramidite) 0 (Nucleosides) |
| Entry Date(s): | Date Created: 20260630 Date Completed: 20260630 Latest Revision: 20260813 |
| Update Code: | 20260814 |
| PubMed Central ID: | PMC13316733 |
| DOI: | 10.1002/cbic.70347 |
| PMID: | 42375128 |
| Βάση Δεδομένων: | MEDLINE |
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