Palladium-Catalyzed Synthesis of (E)-5-(3-Aminoallyl)-Uridine-5′-O-Triphosphates

Abstract

This unit describes a simple, reliable, and efficient chemical method for the synthesis of 5-(3-aminoallyl)-2′-deoxyuridine-5′-O-triphosphate (AA-dUTP) and 5-(3-aminoallyl)-uridine-5′-O-triphosphate (AA-UTP), starting from the corresponding nucleoside triphosphate. The presented strategy involves regioselective iodination of nucleoside triphosphate using N-iodosuccinimide followed by the palladium-catalyzed Heck coupling with allylamine to provide the corresponding (E)-5-aminoallyl-uridine-5′-O-triphosphate in good yields. It is noteworthy that the protocol not only provides a high-purity product but also eliminates the use of toxic mercuric reagents. © 2017 by John Wiley & Sons, Inc.