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Radical and Radical Ion Reactivity in Nucleic Acid Chemistry

ISBN: 978-0-470-25558-2
466 pages
October 2009
Radical and Radical Ion Reactivity in Nucleic Acid Chemistry (0470255587) cover image
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 theory
  • Ionization of DNA
  • Nucleic acid sugar radicals
  • Halopyrimidines
  • Oxidative, reductive, and low energy electron transfer
  • Electron affinity sensitizers
  • Photochemical generative of reactive oxygen species
  • Reactive nitrogen species
  • Enediyne rearrangements
  • Phenoxyl 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.
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Preface to Series vii

Introduction ix

Contributors xi

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

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

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

4. Reactivity of Nucleic Acid Sugar Radicals 99
Chryssostomos Chatgilialoglu

5. Pyrimidine Nucleobase Radical Reactivity 135
Marc M. Greenberg

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

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

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

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

10. Electronic-Affinic Radiosensitizers 295
Peter Wardman

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

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

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

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

Index 445

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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.

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"Scientists who like to understand life sciences at a molecular level will use these reviews for at least the next 10 years." (Angewandte Chemie, 2010)

"This is a valuable publication and is a worthwhile addition to the library of any researcher who has an interest in any one (or more) of the subtopics discussed."  (JACS, 2010)
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