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Literature DB >> 17988100

(5'S)- and (5'R)-5',8-cyclo-2'-deoxyguanosine: mechanistic insights on the 2'-deoxyguanosin-5'-yl radical cyclization.

Chryssostomos Chatgilialoglu¹, Rita Bazzanini, Liliana B Jimenez, Miguel A Miranda.

Abstract

The two diastereomeric forms (5'S) and (5'R) of 5',8-cyclo-2'-deoxyguanosine have been synthesized and fully characterized. They have been used as references for the investigation of gamma-irradiation of 2'-deoxyguanosine and photolysis of 8-bromo-2'-deoxyguanosine in aqueous solutions. The observed (5'R)/(5'S) ratio of 8:1 was obtained in both sets of experiments. The mechanism of the cyclization reaction is discussed in some detail, and the diastereomeric outcome is rationalized in terms of favorable hydrogen-bonded structures in the pro-(5'R) conformation.

Entities: Chemical

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Year: 2007 PMID： 17988100 DOI： 10.1021/tx700282x

Source DB: PubMed Journal: Chem Res Toxicol ISSN： 0893-228X Impact factor: 3.739

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Cited

16 in total

1. Generation of guanine-thymidine cross-links in DNA by peroxynitrite/carbon dioxide.

Authors: Byeong Hwa Yun; Nicholas E Geacintov; Vladimir Shafirovich
Journal: Chem Res Toxicol Date: 2011-05-04 Impact factor: 3.739

2. Reactivity of Nucleic Acid Radicals.

Authors: Marc M Greenberg
Journal: Adv Phys Org Chem Date: 2016 Impact factor: 2.833

3. Structure and stability of duplex DNA containing (5'S)-5',8-cyclo-2'-deoxyadenosine: an oxidatively generated lesion repaired by NER.

Authors: Tatiana Zaliznyak; Mark Lukin; Carlos de los Santos
Journal: Chem Res Toxicol Date: 2012-09-11 Impact factor: 3.739

4. Structure of (5'S)-8,5'-cyclo-2'-deoxyguanosine in DNA.

Authors: Hai Huang; Rajat S Das; Ashis K Basu; Michael P Stone
Journal: J Am Chem Soc Date: 2011-11-21 Impact factor: 15.419

5. One-electron oxidation of neutral sugar radicals of 2'-deoxyguanosine and 2'-deoxythymidine: a density functional theory (DFT) study.

Authors: Anil Kumar; Venkata Pottiboyina; Michael D Sevilla
Journal: J Phys Chem B Date: 2012-07-27 Impact factor: 2.991

(5'S)- and (5'R)-5',8-cyclo-2'-deoxyguanosine: mechanistic insights on the 2'-deoxyguanosin-5'-yl radical cyclization.

1. Generation of guanine-thymidine cross-links in DNA by peroxynitrite/carbon dioxide.

2. Reactivity of Nucleic Acid Radicals.

3. Structure and stability of duplex DNA containing (5'S)-5',8-cyclo-2'-deoxyadenosine: an oxidatively generated lesion repaired by NER.

4. Structure of (5'S)-8,5'-cyclo-2'-deoxyguanosine in DNA.

5. One-electron oxidation of neutral sugar radicals of 2'-deoxyguanosine and 2'-deoxythymidine: a density functional theory (DFT) study.

6. Free radicals in chemical biology: from chemical behavior to biomarker development.

7. Structures of (5'S)-8,5'-Cyclo-2'-deoxyguanosine Mismatched with dA or dT.

8. Mechanism of Reduction of an Aminyl Radical Intermediate in the Radical SAM GTP 3',8-Cyclase MoaA.

9. Radiation-induced formation of purine lesions in single and double stranded DNA: revised quantification.

10. An ameliorative protocol for the quantification of purine 5',8-cyclo-2'-deoxynucleosides in oxidized DNA.