An Efficient Gram-Scale Chemical Synthesis of UNA-Nucleoside-5'-O-Triphosphates.

Abstract

This unit describes a facile, reliable, and efficient method for the gram-scale chemical synthesis of unlocked nucleic acid- (UNA) nucleoside-5'-O-triphosphates such as UNA-guanosine-5'-O-triphosphate (UNA-GTP), UNA-adenosine-5'-O-triphosphate (UNA-ATP), UNA-cytidine-5'-O-triphosphate (UNA-CTP), and UNA-uridine-5'-O-triphosphate (UNA-UTP), starting from the commercially available corresponding nucleoside-5'-O-triphosphate. The present process involves a "one-pot, two-step" strategy that utilizes green chemistry principles. The overall reaction involves the oxidation of nucleoside-5'-O-triphosphate using sodium periodate under aqueous conditions, followed by reduction using sodium borohydride to furnish the corresponding UNA-nucleoside-5'-O-triphosphate in good yields with high purity (>99.5%). © 2023 Wiley Periodicals LLC. Basic Protocol: Synthesis of UNA-nucleoside-5'-O-triphosphates.