102690-87-9Relevant articles and documents
Synthesis of deoxyadenosine 3′-phosphates bearing cis and trans adducts of 7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo[a] pyrene: Standards for 32P-postlabeling assays
Han, Shin,Harris, Constance M.,Harris, Thomas M.,Kim, Hye-Young Hong,Kim, Seong J.
, p. 174 - 178 (2007/10/03)
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).