Advances in the Application of Pd-Mediated Transformations in Nucleotides and Oligonucleotides

Abstract

Developments in aqueous-phase Pd-catalyzed cross-coupling reactions have provided new opportunities to directly functionalize nucleotides and oligonucleotides (ONs) for a variety of applications, which range from diagnosis to biophysical analysis of nucleic acids to therapeutics. In this review, we first provide a detailed discussion on how chemists have developed and judiciously applied Pd-mediated reactions like Suzuki–Miyaura, Sonogashira, Stille and Heck to synthesize modified nucleotide analogs suitable for enzymatic labeling of nucleic acids. Particular emphasis is given to the applications of labeled ONs derived from incorporation of such modified nucleotides. Following this, new applications of Pd-mediated cross-coupling reactions to postsynthetically functionalize ONs with various biophysical reporters are presented.