NDLI: Electron Attachment to Hydrated Oligonucleotide Dimers: Guanylyl-3′,5′-Cytidine and Cytidylyl-3′,5′-Guanosine

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Electron Attachment to Hydrated Oligonucleotide Dimers: Guanylyl-3′,5′-Cytidine and Cytidylyl-3′,5′-Guanosine

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Xie, Yaoming Schaefer, Henry F. Gu, Jiande
Description	Author Affiliation: Gu J ( Drug Design & Discovery Center, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, CAS, Shanghai 201203, P. R. China. jiandegush@go.com)
Abstract	The dinucleoside phosphate deoxycytidylyl-3′,5′-deoxyguanosine (dCpdG) and deoxyguanylyl-3′,5′-deoxycytidine (dGpdC) systems are among the largest to be studied by reliable theoretical methods. Exploring electron attachment to these subunits of DNA single strands provides significant progress toward definitive predictions of the electron affinities of DNA single strands. The adiabatic electron affinities of the oligonucleotides are found to be sequence dependent. Deoxycytidine (dC) on the 5′ end, dCpdG, has larger adiabatic electron affinity (AEA, 0.90 eV) than dC on the 3′ end of the oligomer (dGpdC, 0.66 eV). The geometric features, molecular orbital analyses, and charge distribution studies for the radical anions of the cytidine-containing oligonucleotides demonstrate that the excess electron in these anionic systems is dominantly located on the cytosine nucleobase moiety. The π-stacking interaction between nucleobases G and C seems unlikely to improve the electron-capturing ability of the oligonucleotide dimers. The influence of the neighboring base on the electron-capturing ability of cytosine should be attributed to the intensified proton accepting–donating interaction between the bases. The present investigation demonstrates that the vertical detachment energies (VDEs) of the radical anions of the oligonucleotides dGpdC and dCpdG are significantly larger than those of the corresponding nucleotides. Consequently, reactions with low activation barriers, such as those for OC σ bond and N-glycosidic bond breakage, might be expected for the radical anions of the guanosine–cytosine mixed oligonucleotides.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	17
Volume Number	16
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2010-05-03
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	DNA, Single-Stranded Chemistry Deoxycytosine Nucleotides Deoxyguanosine Analogs & Derivatives Dinucleoside Phosphates Models, Molecular Electrons Hydrogen Bonding Thermodynamics Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S.
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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