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  Electronic structure of (6−4) DNA photoproduct repair involving a non-oxetane pathway

Domratcheva, T., & Schlichting, I. (2009). Electronic structure of (6−4) DNA photoproduct repair involving a non-oxetane pathway. Journal of the American Chemical Society, 131(49), 17793-17799. doi:10.1021/ja904550d.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-002C-0F56-7 Version Permalink: http://hdl.handle.net/11858/00-001M-0000-002C-0F95-8
Genre: Journal Article
Alternative Title : Electronic structure of (6−4) DNA photoproduct repair involving a non-oxetane pathway

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Domratcheva, Tatiana1, Author              
Schlichting, Ilme1, Author              
Affiliations:
1Department of Biomolecular Mechanisms, Max Planck Institute for Medical Research, Max Planck Society, ou_1497700              

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 Abstract: Mutagenic pyrimidine-pyrimidone (6−4) photoproducts are one of the main DNA lesions induced by solar UV radiation. These lesions can be photoreversed by (6−4) photolyases. The originally published repair mechanism involves rearrangement of the lesion into an oxetane intermediate upon binding to the (6−4) photolyase, followed by light-induced electron transfer from the reduced flavin cofactor. In a recent crystallographic study on a (6−4) photoproduct complexed with (6-4) photolyase from Drosophila melanogaster no oxetane was observed, raising the possibility of a non-oxetane repair mechanism. Using quantum-chemical calculations we find that in addition to repair via an oxetane, a direct transfer of the hydroxyl group results in reversal of the radical anion (6−4) photoproduct. In both mechanisms, the transition states have high energies and correspond to avoided crossings of the ground and excited electronic states. To study whether the repair can proceed via these state crossings, the excited-state potential energy curves were computed. The radical excitation energies and accessibility of the nonadiabatic repair path were found to depend on hydrogen bonds and the protonation state of the lesion. On the basis of the energy calculations, a nonadiabatic repair of the excited (6−4) lesion radical anion via hydroxyl transfer is probable. This repair mechanism is in line with the recent structural data on the (6−4) photolyase from D. melanogaster.

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Language(s): eng - English
 Dates: 2009-06-042009-11-182009-12-16
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: eDoc: 664618
DOI: 10.1021/ja904550d
URI: http://www.ncbi.nlm.nih.gov/pubmed/19921821
Other: 7567
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Title: Journal of the American Chemical Society
  Other : J. Am. Chem. Soc.
  Abbreviation : JACS
Source Genre: Journal
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Publ. Info: American Chemical Society
Pages: - Volume / Issue: 131 (49) Sequence Number: - Start / End Page: 17793 - 17799 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870