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Molecules 2015, 20(5), 9419-9454; doi:10.3390/molecules20059419

Palladium-Catalyzed Modification of Unprotected Nucleosides, Nucleotides, and Oligonucleotides

Department of Chemistry, The University of Alabama, Box 870336, Tuscaloosa, AL 35487-0336, USA
Academic Editor: Mahesh Lakshman
Received: 24 March 2015 / Revised: 15 May 2015 / Accepted: 19 May 2015 / Published: 22 May 2015
(This article belongs to the Special Issue Nucleoside Modifications)

Abstract

Synthetic modification of nucleoside structures provides access to molecules of interest as pharmaceuticals, biochemical probes, and models to study diseases. Covalent modification of the purine and pyrimidine bases is an important strategy for the synthesis of these adducts. Palladium-catalyzed cross-coupling is a powerful method to attach groups to the base heterocycles through the formation of new carbon-carbon and carbon-heteroatom bonds. In this review, approaches to palladium-catalyzed modification of unprotected nucleosides, nucleotides, and oligonucleotides are reviewed. Polar reaction media, such as water or polar aprotic solvents, allow reactions to be performed directly on the hydrophilic nucleosides and nucleotides without the need to use protecting groups. Homogeneous aqueous-phase coupling reactions catalyzed by palladium complexes of water-soluble ligands provide a general approach to the synthesis of modified nucleosides, nucleotides, and oligonucleotides. View Full-Text
Keywords: nucleosides; nucleotides; oligonucleotides; palladium; cross-coupling; aqueous-phase catalysis nucleosides; nucleotides; oligonucleotides; palladium; cross-coupling; aqueous-phase catalysis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Shaughnessy, K.H. Palladium-Catalyzed Modification of Unprotected Nucleosides, Nucleotides, and Oligonucleotides. Molecules 2015, 20, 9419-9454.

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