Synthesis and characterization of the oxidized dGTP lesions spiroiminodihydantoin-2'-deoxynucleoside-5'- triphosphate and guanidinohydantoin-2'-deoxynucleoside-5'- triphosphate.
Two convenient synthetic routes to the oxidized guanosine triphosphate lesions spiroiminodihydantoin-2'-deoxynucleoside-5'-triphosphate (dSpTP) and guanidinohydantoin-2'-deoxynucleoside-5'-triphosphate (dGhTP) are reported. Both two-electron oxidation of 2'-deoxy-7,8-dihydro-8-oxoguanosine-5'-triphosphate (dOGTP) using SO4*- generated photolytically from K2S2O8 or four-electron oxidation of 2'-deoxyguanosine-5'-triphosphate (dGTP) from singlet oxygen provide either dSpTP or dGhTP at pH 8.0 or 4.4, respectively. Highly purified triphosphates are obtained by ion pair reversed-phase HPLC.
Ye
Yu
Y
Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, USA.
Muller
James G
JG
Burrows
Cynthia J
CJ
D003848:Deoxyguanine Nucleotides / Q000737:chemistry*; D006827:Hydantoins / Q000138:chemical synthesis / Q000737:chemistry*; D009711:Nucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D018384:Oxidative Stress
D003848:Deoxyguanine Nucleotides; D006827:Hydantoins; D009711:Nucleotides; C516081:guanidinohydantoin-2'-deoxynucleoside-5'-triphosphate; C516080:spiroiminodihydantoin-2'-deoxynucleoside-5'-triphosphate; C029603:deoxyguanosine triphosphate