Comprehensive coverage of radical reactive intermediates in nucleic acid chemistry and biochemistry

The Wiley Series on Reactive Intermediates in Chemistry and Biology investigates reactive intermediates from the broadest possible range of disciplines. The contributions in each volume offer readers fresh insights into the latest findings, emerging applications, and ongoing research in the field from a diverse perspective.

The chemistry and biochemistry of reactive intermediates is central to organic chemistry and biochemistry, and underlies a significant portion of modern synthetic chemistry.Radical and Radical Ion Reactivity in Nucleic Acid Chemistry provides the only comprehensive review of the chemistry and biochemistry of nucleic acid radical intermediates.

With contributions by world leaders in the field, the text covers a broad range of topics, including:

A discussion of the relevant theoryIonization of DNANucleic acid sugar radicalsHalopyrimidinesOxidative, reductive, and low energy electron transferElectron affinity sensitizersPhotochemical generative of reactive oxygen speciesReactive nitrogen speciesEnediyne rearrangementsPhenoxyl radicals A unique compilation on the cutting edge of our understanding,Radical and Radical Ion Reactivity in Nucleic Acid Chemistry provides an unparalleled resource to student and professional researchers in such fields as organic chemistry, biochemistry, molecular biology, and physical chemistry, as well as the industries associated with these disciplines.

Marc M. Greenberg is a Professor of Chemistry and Director of the Chemistry Biology Interface Graduate Training Program at Johns Hopkins University. His research uses chemistry, biochemistry, and biology to fundamentally understand how DNA is oxidatively damaged, and what the effects of that damage are.

Steven E. Rokita, PhD, is Professor in the Department of Chemistry and Biochemistry at the University of Maryland. His research interests lie in sequence and conformation specific reactions of nucleic acids, enzyme-mediated activation of substrates and coenzymes, halogenation and dehalogenation reactions in biology, aromatic substitution and quinone methide generation in bioorganic chemistry, and copper- and nickel-mediated reactions in bioinorganic chemistry.

Preface to Series vii

Introduction ix

Contributors xi

1. Theoretical Modeling of Radiation-Induced DNA Damage 1Anil Kumar and Michael D. Sevilla

2. Radical Reaction Pathways Initiated by Direct Energy Deposition in DNA by Ionizing Radiation 41William A. Bernhard

3. Chemical Reactions of the Radical Cations of Nucleobases in Isolated and Cellular DNA. Formation of Single-Base Lesions 69Jean Cadet, Thierry Douki, Didier Gasparutto, Jean-Luc Ravanat, and J. Richard Wagner

4. Reactivity of Nucleic Acid Sugar Radicals 99Chryssostomos Chatgilialoglu

5. Pyrimidine Nucleobase Radical Reactivity 135Marc M. Greenberg

6. Reactivity of 5-Halopyrimidines in Nucleic Acids 163Ryu Tashiro and Hiroshi Sugiyama

7. Kinetics of Long-Range Oxidative Electron Transfer Through DNA 191Kiyohiko Kawai and Tetsuro Majima

8. Radical Intermediates During Reductive Electron Transfer Through DNA 211Reji Varghese and Hans-Achim Wagenknecht

9. Low-Energy Electron Interaction with DNA: Bond Dissociation and Formation of Transient Anions, Radicals, and Radical Anions 239Leon Sanche

10. Electronic-Affinic Radiosensitizers 295Peter Wardman

11. Reactions of Reactive Nitrogen Species and Carbonate Radical Anions with DNA 325Vladimir Shafirovich, Conor Crean, and Nicholas E. Geacintov

12. Principles and Applications of Electrochemical Oxidation of Nucleic Acids 357H. Holden Thorp and Julie M. Sullivan

13. DNA Damage Due to Diradical-Generating Cyclizations 389Sean M. Kerwin

14. DNA Damage by Phenoxyl Radicals 421Richard A. Manderville

Index 445