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• W2065655227 endingPage "256" @default.
• W2065655227 startingPage "235" @default.
• W2065655227 abstract "Fourier transform infrared (FTIR) spectra have been obtained from solution samples of the heterocycles uracil, lumazine, and violapterin and reveal interpretable carbonyl stretching frequencies. Spectra of conjugate bases of lumazine and violapterin demonstrate decreases in these carbonyl stretching frequencies upon ionization. Based on isotopic shifts from amide deuterated analogs, semiempirical QCFF/PI calculations were used to assign the vibrational frequencies in the region 1100–1800 cm−1 observed from samples in dimethylsulfoxide (DMSO) and aqueous solutions to specific normal modes. The observed deuterium shifts and the calculations suggest that, in some cases, N—H bending motions are coupled to the C=O stretching motions of the pyrimidine ring. These data suggest that for lumazine anions a change in solvent can significantly change the mixing of the N—H bending and C=O stretching vibrational motions. This implies that vibrational analysis for lumazine species in relatively noninteracting media like nonpolar solvents, mulls or pellets cannot necessarily be transferred to the system when it is dissolved in a polar, hydrogen-bonding solvent such as water. Although other explanations can be offered, our vibrational analysis suggests that the changes in normal mode composition of the predominantly C=O stretching vibrations of lumazine anion on going from dimethylsulfoxide to water solution are consistent with a change in the predominant tautomer of the heterocycle. This change appears to correspond to a shifting of the location of the remaining acidic proton to a different ring nitrogen atom. This interpretation is of interest in view of recent ab initio calculations which suggest that proton shifts may occur during the hydroxylation of lumazine as mediated by the enzyme xanthine oxidase. © 1998 John Wiley & Sons, Inc. Biospectroscopy 4: 235–256, 1998" @default.
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• W2065655227 date "1998-01-01" @default.
• W2065655227 modified "2023-09-27" @default.
• W2065655227 title "FTIR characterization of heterocycles lumazine and violapterin in solution: Effects of solvent on anionic forms" @default.
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• W2065655227 doi "https://doi.org/10.1002/(sici)1520-6343(1998)4:4<235::aid-bspy3>3.0.co;2-1" @default.
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