Frontispiece: 8‐Oxo‐7,8‐dihydroadenine and 8‐Oxo‐7,8‐dihydroadenosine—Chemistry, Structure, and Function in RNA and Their Presence in Natural Products and Potential Drug Derivatives

Abstract

A description and history of the role that 8‐oxo‐7,8‐dihydroadenine (8‐oxoAde) and 8‐oxo‐7,8‐dihydroadenosine (8‐oxoA) have in various fields is provided. This article focuses on 1) the formation of this oxidatively generated modification in RNA, its interactions with other biopolymers, and its potential role in the development/progression of disease; 2) the independent synthesis and incorporation of this modified nucleoside into oligonucleotides of RNA to display the progress that has been made in establishing its behavior in biologically relevant systems; 3) reported synthetic routes, which date back to 1890, along with the progress that has been made in the total synthesis of the nucleobase, nucleoside, and their corresponding derivatives; and 4) the isolation, total synthesis, and biological activity of natural products containing these moieties as the backbone. For more details, see Minireview by M. J. E. Resendiz et al. on page 6706 ff.