8-Oxo-7,8-dihydroadenine and 8-Oxo-7,8-dihydroadenosineChemistry, Structure, and Function in RNA and Their Presence in Natural Products and Potential Drug Derivatives

被引：12

作者：

Choi, Yu Jung ^{[1
]}

Chang, Stephanie J. ^{[1
]}

Gibala, Krzysztof S. ^{[1
]}

Resendiz, Marino J. E. ^{[1
]}

机构：

[1] Univ Colorado Denver, Dept Chem, Sci Bldg,1151 Arapahoe St, Denver, CO 80204 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 28期

关键词：

8-oxoA drug derivatives; natural products; oxidatively damaged RNA; RNA function; UNIMOLECULAR TRANSFORMATION REACTIONS; OXIDATIVELY GENERATED DAMAGE; ANEMONE BUNODOSOMA-CAISSARUM; TANDEM MASS-SPECTROMETRY; BASE-PAIRING PROPERTIES; NUCLEIC-ACID ADDUCTS; OH RADICAL REACTION; N-GLYCOSIDIC BOND; ASMARINES A-F; MARINE SPONGE;

D O I：

10.1002/chem.201605163

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 has been compiled. This Review focusses 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. The current state of research regarding this oxidatively generated lesion as well as its importance in the context of RNA, natural products, and potential as drug derivatives is illustrated using all available examples reported to date.

引用

页码：6706 / +

页数：11

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