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19. Effect of Absolute Configuration on the Optical and NMR Properties of Oligonucleotides Containing Benzo[a]Pyrene Adducts at N6of Deoxyadenosine

Author

Sayer, JaneM., Shah, JamshedH., Liang, Chengyi, Xie, Guojian, Kroth, Heiko, Yagi, Haruhiko, Xiaohongliu, Yeh, HermanJ. C., and Jerina, DonaldM.

Abstract

AbstractFor oligonucleotide duplexes derived from trans opening of benzo[a]pyrene diol epoxides (BaP DEs) by the exocyclic N6-amino group of deoxyadenosine (dA), the hydrocarbon is intercalated toward the 5′-end of the modified strand when the configuration at the site of attachment of the base to the hydrocarbon (C-10) is R, and toward the 3′-end when this configuration is S. In oligonucleotide 11-mer duplexes modified by BaP DE-1 (benzylic 7-OH and epoxide oxygen cis) and DE-2 (7-OH and epoxide oxygen trans), as well as 7,8,9,10-tetrahydro BaP 9,10-epoxide, 10Radducts had consistently higher (5–9d°C) Tmvalues than the corresponding 10Sadducts. Dodecamer duplexes from the HPRTgene with trans opened 10S(but not those with 10R) BaP DE-2 adducts at either of two adjacent dA residues exhibited blue shifts at ∼350 nm at temperatures well below the Tm. We propose that these blue shifts result from a conformation in which the hydrocarbon is not stacked with the DNA bases.

Published
1999
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