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Theoretical study on the characterization of the ribosyl C4'-radical observed in irradiated crystals of uridine

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The angular dependence of the β-hydrogens hyperfine splitting (hfs) constants of the 1′amino 2′-deoxyribosyl C4′-radical (1) has been computed at the B3LYP/6-311G**//UHF/6-31G** level for the S-type (C2′endo ring puckering) and N-type (C3′endo ring puckering) configurations. Good agreement between the theoretical hfs constants and the three large experimental β-hydrogen hfs constants of the radical species observed in irradiated single crystals of uridine has been found only for the N-type configuration with the β5′-oxygen in the staggered conformation. It is concluded that the observed radical species is the uridine C4′-radical (2) that adopts the C3′ endo ring puckering as found in single crystals of uridine by means of neutron diffraction. This conclusion is in contrast with that reached in a previous theoretical study.


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