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J. Biol. Chem., Vol. 277, Issue 14, 11765-11771, April 5, 2002
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Opposite Benzo[a]pyrene 7,8-Diol
9,10-Epoxide Deoxyguanosine Adducts*
,,§,,
,, and§**
From the Human DNA polymerase Laboratory of Bioorganic Chemistry, NIDDK,
National Institutes of Health, Bethesda, Maryland 20892, the
§ Department of Chemistry, American University, Washington,
D. C. 20016, RIKEN and Core Research for Evolutional Science
and Technology, Japan Science and Technology Corporation, Wako,
Saitama 351-0198, Japan, and the ¶ Institute for Molecular and
Cellular Biology, Osaka University, Suita, Osaka 565-0871, Japan
was used to copy four
stereoisomeric deoxyguanosine (dG) adducts derived from
benzo[a]pyrene 7,8-diol 9,10-epoxide (diastereomer with
the 7-hydroxyl group and epoxide oxygen trans (BaP DE-2)). The adducts,
formed by either cis or trans epoxide ring opening of each enantiomer
of BaP DE-2 by N2 of dG, were placed at the
fourth nucleotide from the 5'-end in two 16-mer sequence contexts,
5'~CG*A~ and 5'~GG*T. pol was remarkably error prone at all
four diol epoxide adducts, preferring to misincorporate G and A at
frequencies 3- to more than 50-fold greater than the frequencies for T
or the correct C, although the highest rates were 60-fold below the
rate of incorporation of C opposite a non-adducted G. Anti
to syn rotation of the adducted base, consistent with previous NMR data for a BaP DE-2 dG adduct placed just beyond a primer
terminus, provides a rationale for preferring purine misincorporation.
Extension of purine misincorporations occurred preferentially, but
extension beyond the adduct site was weak with
Vmax/Km values generally
10-fold less than for misincorporation. Mostly A was incorporated
opposite (+)-BaP DE-2 dG adducts, which correlates with published
observations that G 
T is the most common type of mutation that
(+)-BaP DE-2 induces in mammalian cells.
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