%0 Journal Article %A Takamura-Enya, Takeji %A Ishikawa, Satoko %A Mochizuki, Masataka %A Wakabayashi, Keiji %D 2006 %T Chemical Synthesis of 2‘-Deoxyguanosine−C8 Adducts with Heterocyclic Amines:  An Application to Synthesis of Oligonucleotides Site-Specifically Adducted with 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine %U https://acs.figshare.com/articles/journal_contribution/Chemical_Synthesis_of_2_Deoxyguanosine_C8_Adducts_with_Heterocyclic_Amines_An_Application_to_Synthesis_of_Oligonucleotides_Site_Specifically_Adducted_with_2_Amino_1_methyl_6_phenylimidazo_4_5_i_b_i_pyridine/3075493 %R 10.1021/tx050296s.s001 %2 https://acs.figshare.com/ndownloader/files/4781278 %K rat Apc genes %K arylamination reaction %K dG %K TCC GGG AAC %K Cs 2CO base %K Pd 2dba %K HCA %K cesium carbonate %K PhIP adducted %K Subsequent deprotection %K reaction temperature %K G sequence %K deprotection procedures %K DNA synthesis %K codon 869 %K dimethyl sulfoxide %K IQ %K chemical Synthesis %K DMSO %X Synthesis of 2‘-deoxyguanosine−C8 adducts (dG−C8 adducts) with mutagenic/carcinogenic heterocyclic amines (HCAs) was achieved via the Buchwald−Hartwig arylamination reaction. By using tris(dibenzylideneacetone)dipalladium (Pd2dba3) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (xantphos) with a cesium carbonate (Cs2CO3) base at a reaction temperature of 100∼120 °C, we obtained derivatives of dG−C8 adducts with 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), 2-amino-6-methyldipyrido[1,2-a:3‘,2‘-d]imidazole (Glu-P-1), 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1), 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in 69%∼97% yield from the cross-coupling of an 8-bromodeoxyguanosine derivative. In the case of PhIP, it was found that dimethyl sulfoxide (DMSO) was the critical solvent for the arylamination reaction. Subsequent deprotection of the resulting dG−C8 adduct derivatives yielded authentic samples of dG−C8 adducts with HCAs. The dG−C8−PhIP adduct was further converted into a suitably protected phosphoramidite derivative for automated DNA synthesis. Synthesis of oligonucleotides wherein PhIP adducted on each G within a triple G sequence in codon 869 (TCC GGG AAC) of rat Apc genes was performed with a modification in the coupling time and deprotection procedures. %I ACS Publications