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Literature DB >> 1851561

Photo-induced formation of the 2-deoxyribonolactone-containing nucleotide for d(ApCpA); effects of neighboring bases and modification of deoxycytidine.

Abstract

Previously, we reported the formation of a 2-deoxyribonolactone-containing nucleotide by UV irradiation of d(ApCpA). In this paper, we report some mechanical feature of this novel photoreaction. From the results of photolysis of d(GpCpG), this reaction is independent of neighboring bases. On photolysis of deoxycytidine at acidic pH, 2-deoxyribonolactone was produced with 74.2% isolated yield. And effects of some modifications of deoxycytidine were investigated. The results suggest that hydrates are possible intermediates for this reaction and the protonation may be essential not for deoxycytidine, but for the intermediates.

Entities: Chemical

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Year: 1991 PMID： 1851561 PMCID： PMC328103 DOI： 10.1093/nar/19.8.1773

Source DB: PubMed Journal: Nucleic Acids Res ISSN： 0305-1048 Impact factor: 16.971

17 in total

1. Photochemistry of cytosine nucleosides and nucleotides.

Authors: K L WIERZCHOWSKI; D SHUGAR
Journal: Biochim Biophys Acta Date: 1957-08

Review 2. DNA repair in bacteria and mammalian cells.

Authors: P C Hanawalt; P K Cooper; A K Ganesan; C A Smith
Journal: Annu Rev Biochem Date: 1979 Impact factor: 23.643

3. Chemical analysis of DNA alterations. I. Base liberation and backbone breakage of DNA and oligodeoxyadenylic acid induced by hydrogen peroxide and hydroxylamine.

Authors: H J Rhaese; E Freese
Journal: Biochim Biophys Acta Date: 1968-02-26

4. Reaction of hydroxylamine and methoxyamine with the ultraviolet-induced hydrate of cytidine.

Authors: G D Small; M P Gordon
Journal: J Mol Biol Date: 1968-07-14 Impact factor: 5.469

5. Sequence analysis of ultraviolet-induced mutations in M13lacZ hybrid phage DNA.

Authors: J E LeClerc; N L Istock; B R Saran; R Allen
Journal: J Mol Biol Date: 1984-12-05 Impact factor: 5.469

6. Synthetic nucleosides and nucleotides. XXI. On the synthesis and biological evaluations of 2'-deoxy-alpha-D-ribofuranosyl nucleosides and nucleotides.

Authors: T Yamaguchi; M Saneyoshi
Journal: Chem Pharm Bull (Tokyo) Date: 1984-04 Impact factor: 1.645

7. A 2-deoxyribonolactone-containing nucleotide: isolation and characterization of the alkali-sensitive photoproduct of the trideoxyribonucleotide d(ApCpA).

Authors: H Urata; K Yamamoto; M Akagi; H Hiroaki; S Uesugi
Journal: Biochemistry Date: 1989-12-12 Impact factor: 3.162

Review 4. RNA polymerase pausing, stalling and bypass during transcription of damaged DNA: from molecular basis to functional consequences.

Authors: Aleksei Agapov; Anna Olina; Andrey Kulbachinskiy
Journal: Nucleic Acids Res Date: 2022-04-08 Impact factor: 16.971

4 in total

Photo-induced formation of the 2-deoxyribonolactone-containing nucleotide for d(ApCpA); effects of neighboring bases and modification of deoxycytidine.

1. Photochemistry of cytosine nucleosides and nucleotides.

Review 2. DNA repair in bacteria and mammalian cells.

3. Chemical analysis of DNA alterations. I. Base liberation and backbone breakage of DNA and oligodeoxyadenylic acid induced by hydrogen peroxide and hydroxylamine.

4. Reaction of hydroxylamine and methoxyamine with the ultraviolet-induced hydrate of cytidine.

5. Sequence analysis of ultraviolet-induced mutations in M13lacZ hybrid phage DNA.

6. Synthetic nucleosides and nucleotides. XXI. On the synthesis and biological evaluations of 2'-deoxy-alpha-D-ribofuranosyl nucleosides and nucleotides.

7. A 2-deoxyribonolactone-containing nucleotide: isolation and characterization of the alkali-sensitive photoproduct of the trideoxyribonucleotide d(ApCpA).

8. The U.V. photochemistry of cytidylic acid.

9. Photoproduct frequency is not the major determinant of UV base substitution hot spots or cold spots in human cells.

Review 10. Cyclobutane-type pyrimidine dimers in polynucleotides.

1. Translesional synthesis on DNA templates containing the 2'-deoxyribonolactone lesion.

2. Enzyme mechanism-based, oxidative DNA-protein cross-links formed with DNA polymerase β in vivo.

3. 2'-deoxyribonolactone lesion produces G->A transitions in Escherichia coli.

Review 4. RNA polymerase pausing, stalling and bypass during transcription of damaged DNA: from molecular basis to functional consequences.