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Titolo:
Using density functional theory to design DNA base analogues with low oxidation potentials
Autore:
Baik, MH; Silverman, JS; Yang, IV; Ropp, PA; Szalai, VA; Yang, WT; Thorp, HH;
Indirizzi:
Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA Univ N Carolina Chapel Hill NC USA 27599 Chem, Chapel Hill, NC 27599 USA Duke Univ, Dept Chem, Durham, NC 27708 USA Duke Univ Durham NC USA 27708Duke Univ, Dept Chem, Durham, NC 27708 USA
Titolo Testata:
JOURNAL OF PHYSICAL CHEMISTRY B
fascicolo: 27, volume: 105, anno: 2001,
pagine: 6437 - 6444
SICI:
1520-6106(20010712)105:27<6437:UDFTTD>2.0.ZU;2-Q
Fonte:
ISI
Lingua:
ENG
Soggetto:
ELECTRON-REDUCTION POTENTIALS; INTRAMOLECULAR PROTON-TRANSFER; REDOX POTENTIALS; AQUEOUS-SOLUTION; CHARGE-TRANSFER; PROTEIN ENVIRONMENTS; TRANSITION-METALS; P-BENZOQUINONES; HOLE TRANSPORT; NUCLEIC-ACIDS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
74
Recensione:
Indirizzi per estratti:
Indirizzo: Thorp, HH Univ N Carolina, Dept Chem, CB 3290, Chapel Hill, NC 27599 USA Univ N Carolina CB 3290 Chapel Hill NC USA 27599 l, NC 27599 USA
Citazione:
M.H. Baik et al., "Using density functional theory to design DNA base analogues with low oxidation potentials", J PHYS CH B, 105(27), 2001, pp. 6437-6444

Abstract

The oxidizability of substituted nucleobases was evaluated through theoretical calculations and the ability of individual bases to induce current enhancement in the cyclic voltammograms of metal complexes. Formation of the guanine derivatives 7-deazaguanine and 8-oxoguanine is known to lower the energy for oxidation of guanine. The similar derivatives of adenine were examined and gave lower predicted redox energies as well as current enhancementwith Ru(bpy)(3)(2+) (7-deazaadenine) and Fe(bpy)(3)(2+) (8-oxoadenine). Oxidizable, substituted pyrimidines were identified using a computational library that gave 5-aminocytosine and 5-aminouracil as promising electron donors. Again, these predictions were verified using catalytic electrochemistry. In addition, the computations predicted that 6-aminocytosine would be redox-active but not as easily oxidized as 5-aminocytosine, which was also confirmed experimentally. In addition to calculating the relative one-electronredox potentials, we used calculations to evaluate the loss of a proton that occurs from the initially formed radical cation. These calculations gaveresults consistent with the experiments, and in the case of 8-oxoadenine, the relative redox reactivity could be predicted only when the proton loss step was considered. These substituted bases constitute building blocks forhighly redox-active nucleic acids, and the associated theoretical model provides powerful predictability for designing new redox-active nucleobases.

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Documento generato il 01/04/20 alle ore 17:48:02