Literature DB >> 10814391

Characterization of spiroiminodihydantoin as a product of one-electron oxidation of 8-Oxo-7,8-dihydroguanosine.

W Luo1, J G Muller, E M Rachlin, C J Burrows.   

Abstract

[reaction: see text] Further oxidation of the common DNA lesion 8-oxo-7,8-dihydroguanosine by one-electron oxidants such as IrCl6(2-), Fe(CN)6(3-), or SO4-* leads to two major products, depending upon reaction conditions. In nucleosides at pH 7, 22 degrees C, the principal product is shown herein to be a spiroiminodihydantoin nucleoside, as a diastereomeric mixture, that can be characterized by NMR, ESI-MS/MS, and independent synthesis.

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Year:  2000        PMID: 10814391     DOI: 10.1021/ol9913643

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  89 in total

1.  Surviving an Oxygen Atmosphere: DNA Damage and Repair.

Authors:  Cynthia J Burrows
Journal:  ACS Symp Ser Am Chem Soc       Date:  2009-12-20

2.  Comparison of Transition Metal-Mediated Oxidation Reactions of Guanine in Nucleoside and Single-Stranded Oligodeoxynucleotide Contexts.

Authors:  Pranjali Ghude; Mark A Schallenberger; Aaron M Fleming; James G Muller; Cynthia J Burrows
Journal:  Inorganica Chim Acta       Date:  2011-04-15       Impact factor: 2.545

Review 3.  Biologically relevant oxidants and terminology, classification and nomenclature of oxidatively generated damage to nucleobases and 2-deoxyribose in nucleic acids.

Authors:  Jean Cadet; Steffen Loft; Ryszard Olinski; Mark D Evans; Karol Bialkowski; J Richard Wagner; Peter C Dedon; Peter Møller; Marc M Greenberg; Marcus S Cooke
Journal:  Free Radic Res       Date:  2012-02-22

4.  pH-Dependent Equilibrium between 5-Guanidinohydantoin and Iminoallantoin Affects Nucleotide Insertion Opposite the DNA Lesion.

Authors:  Judy Zhu; Aaron M Fleming; Anita M Orendt; Cynthia J Burrows
Journal:  J Org Chem       Date:  2015-11-24       Impact factor: 4.354

5.  Independent Generation and Reactivity of 2'-Deoxyguanosin-N1-yl Radical.

Authors:  Liwei Zheng; Marc M Greenberg
Journal:  J Org Chem       Date:  2020-06-11       Impact factor: 4.354

6.  Guanine oxidation product 5-carboxamido-5-formamido-2-iminohydantoin induces mutations when bypassed by DNA polymerases and is a substrate for base excision repair.

Authors:  Omar R Alshykhly; Aaron M Fleming; Cynthia J Burrows
Journal:  Chem Res Toxicol       Date:  2015-09-02       Impact factor: 3.739

7.  The Nonbulky DNA Lesions Spiroiminodihydantoin and 5-Guanidinohydantoin Significantly Block Human RNA Polymerase II Elongation in Vitro.

Authors:  Marina Kolbanovskiy; Moinuddin A Chowdhury; Aditi Nadkarni; Suse Broyde; Nicholas E Geacintov; David A Scicchitano; Vladimir Shafirovich
Journal:  Biochemistry       Date:  2017-06-07       Impact factor: 3.162

8.  2'-Fluorinated Hydantoins as Chemical Biology Tools for Base Excision Repair Glycosylases.

Authors:  Sheng Cao; JohnPatrick Rogers; Jongchan Yeo; Brittany Anderson-Steele; Jonathan Ashby; Sheila S David
Journal:  ACS Chem Biol       Date:  2020-03-13       Impact factor: 5.100

9.  Reconciliation of chemical, enzymatic, spectroscopic and computational data to assign the absolute configuration of the DNA base lesion spiroiminodihydantoin.

Authors:  Aaron M Fleming; Anita M Orendt; Yanan He; Judy Zhu; Rina K Dukor; Cynthia J Burrows
Journal:  J Am Chem Soc       Date:  2013-11-21       Impact factor: 15.419

10.  Influence of substrate complexity on the diastereoselective formation of spiroiminodihydantoin and guanidinohydantoin from chromate oxidation.

Authors:  Julia N Gremaud; Brooke D Martin; Kent D Sugden
Journal:  Chem Res Toxicol       Date:  2010-02-15       Impact factor: 3.739

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