caa a22 4500 605487782 CHVBK 20210128100452.0 cr unu---uuuuu 210128e20150301xx s 000 0 eng 10.1007/s00214-015-1631-9 doi (NATIONALLICENCE)springer-10.1007/s00214-015-1631-9 DFT investigation of the formation of linear aminols as the first step toward the induction of oxidatively generated interstrand cross-link DNA lesions [Elektronische Daten] [Raymond Grüber, Élise Dumont] Apyrimidinic/apurinic sites feature among the most prevalent DNA lesions. If not repaired, it has been recently evidenced that they are prone to react in situ with vicinal nucleobases, evolving toward more complex and highly mutagenic interstrand cross-links. Information concerning the structure and the multi-step reactivity leading to such clustered defects is scarce due to their low formation yield. This study reports a DFT exploration of the condensation reaction between a ketoaldehyde (derived from an oxidized C4' abasic site) and three nucleobases featuring an amino group. They are found to present a very similar intrinsic reactivity, indicating in turn that differences of reactivity arise more from the relative positioning of the two reactive fragments within a flexible B-DNA. We also probe the role of a vicinal water molecule for the formation of the aminol and the requirements to reach an adequate estimate of this strongly exothermic reaction, which drives the DNA damage process. Springer-Verlag Berlin Heidelberg, 2015 DNA interstrand cross-link nationallicence Oxidized abasic site nationallicence Density functional theory nationallicence Reactivity nationallicence Dispersion nationallicence Grüber Raymond Institut de Chimie de Lyon, CNRS, Ecole Normale Supérieure de Lyon, Université de Lyon, 46 allée d'Italie, 69364, Lyon, Cedex 07, France aut Dumont Élise Institut de Chimie de Lyon, CNRS, Ecole Normale Supérieure de Lyon, Université de Lyon, 46 allée d'Italie, 69364, Lyon, Cedex 07, France aut Theoretical Chemistry Accounts Springer Berlin Heidelberg 134/3(2015-03-01), 1-7 1432-881X 134:3<1 2015 134 214 https://doi.org/10.1007/s00214-015-1631-9 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s00214-015-1631-9 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Grüber Raymond Institut de Chimie de Lyon, CNRS, Ecole Normale Supérieure de Lyon, Université de Lyon, 46 allée d'Italie, 69364, Lyon, Cedex 07, France aut NATIONALLICENCE 700 1- Dumont Élise Institut de Chimie de Lyon, CNRS, Ecole Normale Supérieure de Lyon, Université de Lyon, 46 allée d'Italie, 69364, Lyon, Cedex 07, France aut NATIONALLICENCE 773 0- Theoretical Chemistry Accounts Springer Berlin Heidelberg 134/3(2015-03-01), 1-7 1432-881X 134:3<1 2015 134 214