Synthesis of the Fully Protected Phosphoramidite of the Benzene-DNA Adduct,N²-(4-Hydroxyphenyl)-2′-Deoxyguanosine and Incorporation of the Later into DNA Oligomers

Abstract

Enzymatic hydrolysis and HPLC analysis confirmed the presence of this adduct in the oligomers.

Nucleotides and Nucleic Acids; Oligo- and Polynucleotides

“…242 The adduct N 2 -(4-hydroxyphenyl)-dG is reported to be derived from exposure to benzene, and has been synthesised as its phosphoramidite building block and incorporated into DNA, but no further detail is supplied. 243 The benzo[a]pyrene adduct (52) (10S( þ )-trans-anti-isomer shown) is derived from an environmental mutagen and acts as a blocking lesion to many polymerases. The Y-family DNA polymerase Dpo4 from Sulfolobus solfataricus is able to bypass the lesion by inserting dAMP opposite to a thymidine on the 5 0 side of the adduct, producing a -1 deletion sequence.…”