دورية أكاديمية
Evidence for glycosidic bond rotation in a nucleobase peroxyl radical and its effect on tandem lesion formation.
| العنوان: | Evidence for glycosidic bond rotation in a nucleobase peroxyl radical and its effect on tandem lesion formation. |
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| المؤلفون: | Hong IS; Department of Chemistry, Johns Hopkins University, 3400 N. Charles St., Baltimore, Maryland 21218, USA., Carter KN, Greenberg MM |
| المصدر: | The Journal of organic chemistry [J Org Chem] 2004 Oct 15; Vol. 69 (21), pp. 6974-8. |
| نوع المنشور: | Journal Article; Research Support, U.S. Gov't, P.H.S. |
| اللغة: | English |
| بيانات الدورية: | Publisher: American Chemical Society Country of Publication: United States NLM ID: 2985193R Publication Model: Print Cited Medium: Print ISSN: 0022-3263 (Print) Linking ISSN: 00223263 NLM ISO Abbreviation: J Org Chem Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: Columbus Oh : American Chemical Society Original Publication: Easton, Pa. [etc.] |
| مواضيع طبية MeSH: | DNA Damage*, DNA/*chemistry , Free Radicals/*chemistry , Glycosides/*chemistry , Nucleosides/*chemistry , Nucleosides/*radiation effects, DNA/radiation effects ; Free Radicals/radiation effects ; Glycosides/radiation effects ; Models, Molecular ; Nucleic Acid Conformation ; Pulse Radiolysis ; Stereoisomerism |
| مستخلص: | Nucleobase peroxyl radicals are the major reactive intermediates formed in DNA when the biopolymer is exposed to gamma-radiolysis under aerobic conditions. The major reaction pathways for the peroxyl radical (1) derived from 5,6-dihydro-2'-deoxyuridin-6-yl involve pi-bond addition to or hydrogen atom abstraction from the adjacent nucleotides to produce tandem lesions. The ability to independently generate 1 at a defined site in DNA enabled us to probe its reactivity by varying the local DNA structure. The effect of DNA structure variation reveals that 1 reacts from its syn- and anti-conformations in competition with trapping by thiol. These experiments also reveal that tandem lesions will be produced as a mixture of diastereomers, which could impact their biological effects. |
| معلومات مُعتمدة: | GM-054996 United States GM NIGMS NIH HHS |
| المشرفين على المادة: | 0 (Free Radicals) 0 (Glycosides) 0 (Nucleosides) 9007-49-2 (DNA) |
| تواريخ الأحداث: | Date Created: 20041009 Date Completed: 20041222 Latest Revision: 20071114 |
| رمز التحديث: | 20240628 |
| DOI: | 10.1021/jo0492158 |
| PMID: | 15471441 |
| قاعدة البيانات: | MEDLINE |
Find this issue from the American Chemical Society | تدمد: | 0022-3263 |
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| DOI: | 10.1021/jo0492158 |