Chemistry - A European Journal, volume 23, issue 31, pages 7526-7537

Indications of 5′ to 3′ Interbase Electron Transfer as the First Step of Pyrimidine Dimer Formation Probed by a Dinucleotide Analog

Jian Yajun ^{1, 2}

Maximowitsch Egle ³

Liu Degang ¹

Adhikari Surya ¹

Li Lei ^{1, 4}

Domratcheva Tatiana ³

Hide authors affiliations Show authors affiliations: 4 affiliations

Department of Chemistry and Chemical Biology; Indiana University-Purdue University Indianapolis (IUPUI); 402 North Blackford Street Indianapolis Indiana 46202 USA |

School of Chemistry & Chemical Engineering; Shaanxi Normal University (SNNU); No. 620, West Chang'an Avenue, Xi'an Shaanxi 710119 P. R. China |

Department of Biomolecular Mechanisms; Max-Planck Institute for Medical Research; Jahnstrasse 29 69120 Heidelberg Germany |

⁴

Department of Dermatology; Indiana University School of Medicine; Indianapolis Indiana 46202 USA |

Publication type: Journal Article

Publication date: 2017-05-15

Wiley

Journal: Chemistry - A European Journal

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Quartile WOS

Impact factor: 4.3

ISSN: 09476539, 15213765

DOI: 10.1002/chem.201700045

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General Chemistry

Catalysis

Organic Chemistry

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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Citations by journals

	1
Faraday Discussions	Faraday Discussions, 1, 12.5% Faraday Discussions 1 publication, 12.5%
Nature Communications	Nature Communications, 1, 12.5% Nature Communications 1 publication, 12.5%
Photochemical and Photobiological Sciences	Photochemical and Photobiological Sciences, 1, 12.5% Photochemical and Photobiological Sciences 1 publication, 12.5%
Bioorganic Chemistry	Bioorganic Chemistry, 1, 12.5% Bioorganic Chemistry 1 publication, 12.5%
Chemistry - A European Journal	Chemistry - A European Journal, 1, 12.5% Chemistry - A European Journal 1 publication, 12.5%
FEBS Letters	FEBS Letters, 1, 12.5% FEBS Letters 1 publication, 12.5%
Synlett	Synlett, 1, 12.5% Synlett 1 publication, 12.5%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 1, 12.5% Organic and Biomolecular Chemistry 1 publication, 12.5%
	1

Citations by publishers

	1 2
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 2, 25% Royal Society of Chemistry (RSC) 2 publications, 25%
Springer Nature	Springer Nature, 2, 25% Springer Nature 2 publications, 25%
Wiley	Wiley, 2, 25% Wiley 2 publications, 25%
Elsevier	Elsevier, 1, 12.5% Elsevier 1 publication, 12.5%
Thieme	Thieme, 1, 12.5% Thieme 1 publication, 12.5%
	1 2

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Jian Y. et al. 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. 2017. Vol. 23. No. 31. pp. 7526-7537.

GOST all authors (up to 50) Copy

Jian Y., Maximowitsch E., Liu D., Adhikari S., Li L., Domratcheva T. 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. 2017. Vol. 23. No. 31. pp. 7526-7537.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1002/chem.201700045

UR - https://doi.org/10.1002%2Fchem.201700045

TI - Indications of 5′ to 3′ Interbase Electron Transfer as the First Step of Pyrimidine Dimer Formation Probed by a Dinucleotide Analog

T2 - Chemistry - A European Journal

AU - Jian, Yajun

AU - Maximowitsch, Egle

AU - Liu, Degang

AU - Adhikari, Surya

AU - Li, Lei

AU - Domratcheva, Tatiana

PY - 2017

DA - 2017/05/15 00:00:00

PB - Wiley

SP - 7526-7537

IS - 31

VL - 23

SN - 0947-6539

SN - 1521-3765

ER -

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BibTex Copy

@article{2017_Jian,

author = {Yajun Jian and Egle Maximowitsch and Degang Liu and Surya Adhikari and Lei Li and Tatiana Domratcheva},

title = {Indications of 5′ to 3′ Interbase Electron Transfer as the First Step of Pyrimidine Dimer Formation Probed by a Dinucleotide Analog},

journal = {Chemistry - A European Journal},

year = {2017},

volume = {23},

publisher = {Wiley},

month = {may},

url = {https://doi.org/10.1002%2Fchem.201700045},

number = {31},

pages = {7526--7537},

doi = {10.1002/chem.201700045}

}

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Jian, Yajun, et al. “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, vol. 23, no. 31, May. 2017, pp. 7526-7537. https://doi.org/10.1002%2Fchem.201700045.

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Publisher

Wiley

Journal

Chemistry - A European Journal

Quartile SCImago

Quartile WOS

Impact factor

4.3

ISSN

09476539 (Print)
15213765 (Electronic)

Profiles

Domratcheva, T