Covalent Modification of Nucleobases using Water-Soluble Palladium Catalysts.
Kevin H ShaughnessyPublished in: Chemical record (New York, N.Y.) (2022)
Nucleosides represent one of the key building blocks of biochemistry. There is significant interest in the synthesis of nucleoside-derived materials for applications as probes, biochemical models, and pharmaceuticals. Palladium-catalyzed cross-coupling reactions are effective methods for making covalent modification of carbon and nitrogen sites on nucleobases under mild conditions. Water-soluble catalysts derived from palladium and hydrophilic ligands, such as tris(3-sulfonatophenyl)phosphine trisodium (TPPTS), are efficient catalysts for a range of coupling reactions of unprotected halonucleosides. Over the past two decades, these methods have been extended to direct functionalization of halonucleotides, as well as RNA and DNA oligonucleotides (ONs) containing halogenated bases. These methods can be run under biocompatible conditions, including examples of Suzuki coupling of modified DNA in whole cells and tissue samples. In this account, development of this methodology by our group and others is highlighted along with the extension of these catalyst systems to modification of nucleotides and ONs.
Keyphrases
- water soluble
- highly efficient
- nucleic acid
- single molecule
- room temperature
- reduced graphene oxide
- metal organic framework
- circulating tumor
- induced apoptosis
- cell free
- transition metal
- ionic liquid
- small molecule
- cell cycle arrest
- oxidative stress
- drug release
- signaling pathway
- mass spectrometry
- fluorescence imaging
- high resolution
- endoplasmic reticulum stress
- photodynamic therapy
- circulating tumor cells