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- W2053638983 abstract "Purines and pyrimidines that form the nucleobases in normal and modified DNA and RNA are known to exist in several tautomeric and ionization states. The relative populations of tautomers in solution and their precise structure are highly sensitive to ring substitution and pH. Knowing the structures in different environments is essential to understand the detailed chemistry of purine modifying enzymes such as ribosyl transferases and DNA glycosylases. We used ultraviolet Raman spectroscopy in resonance with nucleobases and exhaustive DFT calculations to reliably identify solution structures of several nucleic acid enzyme substrates at different pH and established their vibrational signatures. We find that the DNA damage lesion 8oxoguanosine is in the diketone form at physiological pH. At high pH, the anion is formed via deprotonation at N1 while the enolic form was not detected. Hypoxanthine exists as a mixture of the N7H and N9H forms though xanthine exists as a single diketone tautomer in solution. Xanthine is neutral at pH 7 but pKa changes accompany formation of the corresponding mononucleotide which is found to exist predominantly in the deprotonated form at this pH. The vibrational spectra show systematic shifts correlated with protonation state with an overall reduction in the wavenumbers of the purine ring vibrations upon deprotonation. The spectral signatures of purines established here can be used to selectively observe nucleic acid-protein interaction." @default.
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- W2053638983 date "2010-01-01" @default.
- W2053638983 modified "2023-09-30" @default.
- W2053638983 title "Solution Structures and Ultraviolet Raman Spectra of Purines Reveal Systematic Shifts with Change in Protonation State" @default.
- W2053638983 doi "https://doi.org/10.1016/j.bpj.2009.12.3603" @default.
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