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

Molecules

Kevin H. Shaughnessy¹ 

[1] Department of Chemistry, The University of Alabama, Box 870336, Tuscaloosa, AL 35487-0336, USA; E-Mail

关键词: nucleosides;    nucleotides;    oligonucleotides;    palladium;    cross-coupling;    aqueous-phase catalysis;   

DOI  :  10.3390/molecules20059419

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.