{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,5]],"date-time":"2026-07-05T01:20:45Z","timestamp":1783214445301,"version":"3.54.6"},"reference-count":41,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2009,11,20]],"date-time":"2009-11-20T00:00:00Z","timestamp":1258675200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemPhysChem"],"published-print":{"date-parts":[[2010,1,18]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p><jats:italic>To elucidate the role of guanosine in DNA strand breaks caused by low\u2010energy electrons (LEEs), theoretical investigations of the LEE attachment\u2010induced C\uf8ffO \u03c3\u2010bonds and N\u2010glycosidic bond breaking of 2\u2032\u2010deoxyguanosine\u20103\u2032,5\u2032\u2010diphosphate (3\u2032,5\u2032\u2010dGMP) were performed using the B3LYP\/DZP++ approach. The results reveal possible reaction pathways in the gas phase and in aqueous solutions. In the gas phase LEEs could attach to the phosphate group adjacent to the guanosine to form a radical anion. However, the small vertical detachment energy (VDE) of the radical anion of guanosine 3\u2032,5\u2032\u2010diphosphate in the gas phase excludes either C\uf8ffO bond cleavage or N\u2010glycosidic bond breaking. In the presence of the polarizable surroundings, the solvent effects dramatically increase the electron affinities of the 3\u2032,5\u2032\u2010dGDP and the VDE of 3\u2032,5\u2032\u2010dGDP<jats:sup>\u2212<\/jats:sup>. Furthermore, the solvent\u2013solute interactions greatly reduce the activation barriers of the C\uf8ffO bond cleavage to 1.06\u20133.56 kcal\u2009mol<jats:sup>\u22121<\/jats:sup>. These low\u2010energy barriers ensure that either C<jats:sub>5\u2032<\/jats:sub>\uf8ffO<jats:sub>5\u2032<\/jats:sub> or C<jats:sub>3\u2032<\/jats:sub>\uf8ffO<jats:sub>3\u2032<\/jats:sub> bond rupture takes place at the guanosine site in DNA single strands. On the other hand, the comparatively high energy barrier of the N\u2010glycosidic bond rupture implies that this reaction pathway is inferior to C\uf8ffO bond cleavage. Qualitative agreement was found between the theoretical sequence of the bond breaking reaction pathways in the PCM model and the ratio for the corresponding bond breaks observed in the experiment of LEE\u2010induced damage in oligonucleotide tetramer CGTA. This concord suggests that the influence of the surroundings in the thin solid film on the LEE\u2010induced DNA damage resembles that of the solvent.<\/jats:italic><\/jats:p>","DOI":"10.1002\/cphc.200900656","type":"journal-article","created":{"date-parts":[[2009,11,20]],"date-time":"2009-11-20T13:18:01Z","timestamp":1258723081000},"page":"175-181","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":23,"title":["Comprehensive Analysis of DNA Strand Breaks at the Guanosine Site Induced by Low\u2010Energy Electron Attachment"],"prefix":"10.1002","volume":"11","author":[{"given":"Jiande","family":"Gu","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jing","family":"Wang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jerzy","family":"Leszczynski","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2010,1,8]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.287.5458.1658"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevLett.90.208102"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevLett.91.113201"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevLett.90.188104"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0388562"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja036509m"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja029527x"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.cplett.2004.02.022"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp013861i"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja049876m"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp049728i"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp035957d"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0400990"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja054129q"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0407020102"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0510406103"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.2166364"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja063309c"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar0680769"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1140\/epjd\/e2005-00206-6"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1667\/RR3568.1"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.2307\/3579049"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp070800x"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0301-0104(98)00361-9"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja003814o"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja030487m"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja055615g"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevLett.93.068101"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkm135"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja805000g"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr990044u"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp0515535"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.2774985"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevB.37.785"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.464913"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1016\/0009-2614(96)00349-1"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.1696113"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.1674408"},{"key":"e_1_2_6_39_2","first-page":"1","volume-title":"Modern Theoretical Chemistry, Vol. 3","author":"Dunning T. 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