Characterization of spiroiminodihydantoin as a product of one-electron oxidation of 8-Oxo-7,8-dihydroguanosine.
[reaction: see text] Further oxidation of the common DNA lesion 8-oxo-7,8-dihydroguanosine by one-electron oxidants such as IrCl6(2-), Fe(CN)6(3-), or SO4-* leads to two major products, depending upon reaction conditions. In nucleosides at pH 7, 22 degrees C, the principal product is shown herein to be a spiroiminodihydantoin nucleoside, as a diastereomeric mixture, that can be characterized by NMR, ESI-MS/MS, and independent synthesis.
Luo
W
W
Department of Chemistry, University of Utah, Salt Lake City 84112-0850, USA.
Muller
J G
JG
Rachlin
E M
EM
Burrows
C J
CJ
D018360:Crystallography, X-Ray; D004583:Electrons; D006151:Guanosine / Q000031:analogs & derivatives* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000737:chemistry*
D013141:Spiro Compounds; C408822:spiroiminodihydantoin; D006151:Guanosine; C046215:8-hydroxyguanosine