Advices For Studying Organic Chemistry

OH

O

HO

enzymatic

epoxidation

DNA

Dibenzo[a,l]pyrene Dibenzo[a,l]pyrene-11,12-diol-13,14-epoxide

("activation")

deoxyadenosine adduct

2. The normal pathway toward excretion of foreign molecules like aflatoxin B 1 and
   dibenzo[a,l]pyrene, however, also involves nucleophilic substitution reactions of
   their epoxides.

enzymatic

epoxidation

("activation")

+H 3 N

HN

NH CO 2 −

CO 2 −

O SH

S

O

Galutathione

O

O

H

H

OCH 3

O O

O

O

H

H

OCH 3

O O

O

Aflatoxin B (^1) epoxide ring
opening by glutathion
O
O
H
H
OCH 3
O O
HO
+H 3 N
HN
NH CO 2 −
CO 2 −
O
O
Afltatoxin B 1 -gultathione adduct
i) One pathway involves opening of the epoxide ring by nucleophilic substitution