Cited by 1,018DNA and Nucleic Acid ChemistryMetal-Catalyzed Oxygenation MechanismsChemical Reaction Mechanisms

Oxidative Strand Scission of Nucleic Acids: Routes Initiated by Hydrogen Abstraction from the Sugar Moiety

Pogozelski, Wendy Knapp, Tullius, Thomas D.·1998·Chemical Reviews

Abstract

ADVERTISEMENT RETURN TO ISSUEPREVarticleNEXTOxidative Strand Scission of Nucleic Acids: Routes Initiated by Hydrogen Abstraction from the Sugar MoietyWendy Knapp PogozelskiWendy Knapp PogozelskiDepartment of Chemistry, State University of New York at Geneseo, Geneseo, New York 14454, and Department of Chemistry, Boston University, Boston, Massachusetts 02215 More by Wendy Knapp Pogozelski and Thomas D. Tullius*Thomas D. TulliusDepartment of Chemistry, State University of New York at Geneseo, Geneseo, New York 14454, and Department of Chemistry, Boston University, Boston, Massachusetts 02215 To whom correspondence should be addressed.More by Thomas D. TulliusCite this: Chem. Rev. 1998, 98, 3, 1089–1108Publication Date (Web):April 21, 1998Publication History Received27 August 1997Revised26 February 1998Published online21 April 1998Published inissue 7 May 1998https://pubs.acs.org/doi/10.1021/cr960437ihttps://doi.org/10.1021/cr960437iresearch-articleACS PublicationsCopyright © 1998 American Chemical SocietyRequest reuse permissionsArticle Views3930Altmetric-Citations915LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Carbohydrates,Crystal cleavage,Genetics,Hydrogen,Hydrogen abstraction Get e-Alerts

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  • 5-Hydroxymethyluracil and 5-formyluracil are the main hydroxyl-radical-mediated methyl oxidation products of thymine.

    “5-Hydroxymethyluracil (HmUra) and 5-formyluracil (ForUra) have also been characterized as the main • OH-mediated methyl oxidation products of thymine (109).”
  • Hydroxyl radicals efficiently react with 2-deoxyribose moieties by hydrogen abstraction, leading mostly to DNA strand breaks.

    “It may be added that • OH efficiently reacts with the 2-deoxyribose moieties by hydrogen abstraction according to several pathways that lead in most cases to the formation of DNA strand breaks (109).”
  • Hydroxyl radicals react with pyrimidine bases at the C5-C6 double bond, forming 5,6-dihydroxy-5,6-dihydrothymine and 5,6-dihydroxy-5,6-dihydrocytosine.

    “It is also well documented that • OH is able to react with pyrimidine bases at the C5-C6 double bond, leading to the formation of 5,6-dihydroxy-5,6-dihydrothymine (ThyGl) and 5,6-dihydroxy-5,6-dihydrocytosine (109).”

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Authors
Pogozelski, W. K., & Tullius, T. D.
Affiliations
Boston University (US)
Corresponding author
Tullius, Thomas D.
Venue
Chemical Reviews
Published
1998-04-21
Volume
98
Issue
3
Pages
1089-1108
ISSN
  • 0009-2665 (ISSN-L)
  • 1520-6890
OpenAlex
W2027784487
Cited by
1,018
References
141
Citations by year
2026: 8 · 2025: 14 · 2024: 13 · 2023: 15 · 2022: 13 · 2021: 20 · 2020: 16 · 2019: 24 · 2018: 29 · 2017: 34 · 2016: 29 · 2015: 44 · 2014: 59 · 2013: 46 · 2012: 67
FWCI
2.33
Type
journal article
Language
en
Open access
closed
Locations
  • Chemical Reviews (publishedVersion)
  • PubMed (publishedVersion)
Funders
  • State University of New York
  • Lehigh University
  • National Institute of General Medical Sciences (R01GM040894)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
  • Physical Sciences › Chemistry › Inorganic Chemistry › Metal-Catalyzed Oxygenation Mechanisms
  • Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
Keywords
nucleic acids, hydrogen abstraction, sugar moiety, DNA damage, DNA oxidation, reactive oxygen species, hydroxyl radicals, DNA strand breaks, DNA repair, DNA glycosylase

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