Abstract
AbstractExchanging the ribose backbone of an oligonucleotide for a peptide can enhance its physiologic stability and nucleic acid binding affinity. Ordinarily, the eneamino nitrogen atom of a nucleobase is fused to the side chain of a polypeptide through a new C−N bond. The discovery of C−C linked nucleobases in the human transcriptome reveals new opportunities for engineering nucleopeptides that replace the traditional C−N bond with a non‐classical C−C bond, liberating a captive nitrogen atom and promoting new hydrogen bonding and π‐stacking interactions. We report the first late‐stage synthesis of C−C linked carba‐nucleopeptides (cNPs) using aqueous Rhodamine B photoredox catalysis. We prepare brand‐new cNPs in batch, in parallel, and in flow using three long‐wavelength photochemical setups. We detail the mechanism of our reaction by experimental and computational studies and highlight the essential role of diisopropylethylamine as a bifurcated two‐electron reductant.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
