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  Indications of 5' to 3' interbase electron transfer as the first step of pyrimidine dimer formation probed by a dinucleotide analog

Jian, Y., Maximowitsch, E., Liu, D., Adhikari, S., Li, L., & Domratcheva, T. (2017). Indications of 5' to 3' interbase electron transfer as the first step of pyrimidine dimer formation probed by a dinucleotide analog. Chemistry – A European Journal, 23(31), 7526-7537. doi:10.1002/chem.201700045.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0001-3FE5-7 Version Permalink: http://hdl.handle.net/21.11116/0000-0001-3FE6-6
Genre: Journal Article

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 Creators:
Jian, Yajun, Author
Maximowitsch, Eglé1, Author              
Liu, Degang, Author
Adhikari, Surya, Author
Li, Lei, Author
Domratcheva, Tatiana1, Author              
Affiliations:
1Department of Biomolecular Mechanisms, Max Planck Institute for Medical Research, Max Planck Society, ou_1497700              

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Free keywords: DNA photochemistry; electron transfer; pyrimidine (6-4) pyrimidone photoproduct; spore photoproduct; thymine dimer
 Abstract: Pyrimidine dimers are the most common DNA lesions generated under UV radiation. To reveal the molecular mechanisms behind their formation, it is of significance to reveal the roles of each pyrimidine residue. We thus replaced the 5'-pyrimidine residue with a photochemically inert xylene moiety (X). The electron-rich X can be readily oxidized but not reduced, defining the direction of interbase electron transfer (ET). Irradiation of the XpT dinucleotide under 254 nm UV light generates two major photoproducts: a pyrimidine (6-4) pyrimidone analog (6-4PP) and an analog of the so-called spore photoproduct (SP). Both products are formed by reaction at C4=O of the photo-excited 3'-thymidine (T), which indicates that excitation of a single "driver" residue is sufficient to trigger pyrimidine dimerization. Our quantum-chemical calculations demonstrated that photo-excited 3'-T accepts an electron from 5'-X. The resulting charge-separated radical pair lowers its energy upon formation of interbase covalent bonds, eventually yielding 6-4PP and SP.

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Language(s): eng - English
 Dates: 2017-01-042017-05-152017-05-152017-06-01
 Publication Status: Published in print
 Pages: 12
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 Table of Contents: -
 Rev. Method: Peer
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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 23 (31) Sequence Number: - Start / End Page: 7526 - 7537 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058