S. Han, C. Harris, T. Harris
Jan 12, 1996
Citations
0
Influential Citations
7
Citations
Journal
Journal of Organic Chemistry
Abstract
Deoxyadenosine 3‘-phosphates bearing cis and trans N6 adducts of (7R) and (7S)-anti 7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrenes have been prepared in good yield by reaction of 6-fluoropurinyl 2‘-deoxyriboside 3‘-(bis(2-[4-nitrophenyl]ethyl )phosphate with the (±)-(7β,8α,9α,10β)- and (±)-(7β,8α,9α,10α)-10-amino-7,8,9,10-tetrahydrobenzo[a]pyrene-7,8,9-triols. The protected phosphates are easily prepared as diasteromeric mixtures, readily resolved by reversed phase HPLC, and efficiently deprotected with DBU to give the adducted 3‘-phosphates. These nucleotides are of value as standards for the 32P-postlabeling procedure of Randerath for determination of benzo[a]pyrene adducts in DNA (Reddy et al. Carcinogenesis 1984, 5, 231).