Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents

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ID: 300142
1984
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Abstract
The C-8 position of deoxyguanosine (dGuo) was hydroxylated by ascorbic acid in the presence of oxygen (O2) in 0.1 M phosphate buffer (pH 6.8) at 37 degrees C. Addition of hydrogen peroxide (H2O2) remarkably enhanced this hydroxylation. The Udenfriend system [ascorbic acid, FeII, ethylenediaminetetraacetic acid (EDTA) and O2] was also effective for hydroxylation of dGuo in high yield. Guanine residues in DNA were also hydroxylated by ascorbic acid. Other reducing agents, such as hydroxylamine, hydrazine, dihydroxymaleic acid, sodium bisulfite and acetol, were also effective for the hydroxylation reaction, as were metal-EDTA complexes (FeII-, SnII-, TiIII-, CuI-EDTA). An OH radical seemed to be involved in this hydroxylation reaction in most of the above hydroxylating systems, but another reaction mechanism may also be involved, particularly when dGuo is hydroxylated by ascorbic acid alone or ascorbic acid plus H2O2. The possible biological significance of the hydroxylation of guanine residues in DNA in relation to mutagenesis and carcinogenesis is discussed.
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openalex_W2024755124 Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Hiroshi Kasai, Susumu Nishimura
Journal Nucleic Acids Research
Year 1984
DOI
10.1093/nar/12.4.2137
URL
https://doi.org/10.1093/nar/12.4.2137
Keywords Keywords not found

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