ерохide hydrolase P450 HO Но Benzo[a]pyrene BP 7,8-epoxide BP 7,8-dihydrodiol P450 N. NH N. NH Но 1 FIGURE 23.8 Metabolic activation of a carcinogenic polycyclic aromatic hydrocarbon, followed by reaction of the activated dihydrodiol epoxide with DNA но Но OH OH BPDE-deoxyguanosine adduct a DNA DGMP residue. Some H atoms in BP 7,8-dihydrodiol-9,10-epoxide (BPDE) the structures are omitted for simplicity.

Biochemistry
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ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
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Of the four DNA bases, why is guanine most likely to be modified after exposure to polycyclic hydrocarbons such as benzo(a)pyrene, as shown in Figure 23.8? (Hint: Consider the pKa values of the four DNA bases.)

ерохide
hydrolase
P450
HO
Но
Benzo[a]pyrene
BP 7,8-epoxide
BP 7,8-dihydrodiol
P450
N.
NH
N.
NH
Но
1 FIGURE 23.8 Metabolic activation
of a carcinogenic polycyclic aromatic
hydrocarbon, followed by reaction of
the activated dihydrodiol epoxide with
DNA
но
Но
OH
OH
BPDE-deoxyguanosine adduct
a DNA DGMP residue. Some H atoms in
BP 7,8-dihydrodiol-9,10-epoxide
(BPDE)
the structures are omitted for simplicity.
Transcribed Image Text:ерохide hydrolase P450 HO Но Benzo[a]pyrene BP 7,8-epoxide BP 7,8-dihydrodiol P450 N. NH N. NH Но 1 FIGURE 23.8 Metabolic activation of a carcinogenic polycyclic aromatic hydrocarbon, followed by reaction of the activated dihydrodiol epoxide with DNA но Но OH OH BPDE-deoxyguanosine adduct a DNA DGMP residue. Some H atoms in BP 7,8-dihydrodiol-9,10-epoxide (BPDE) the structures are omitted for simplicity.
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