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- W2024901968 abstract "Polycyclic aromatic hydrocarbons are metabolized to a wide variety of oxidized derivatives, including highly reactive diol epoxides which alkylate DNA. The reaction lacks regio- or stereospecificity but occurs primarily at the exocyclic amino groups of deoxyguanosine and deoxyadenosine. An efficient route to N6 adducts of deoxyadenosine is described using as examples those arising from trans opening of the anti-tetrahydrodiol epoxides of naphthalene, benzo[a]pyrene, and benzo[c]phenanthrene. The adducts were synthesized in 50–92% yields by reaction of 6-fluoropurine 2′-deoxyriboside with aminotriols formed by trans opening of racemic dihydrodiol epoxides using liquid NH3. The diastereomeric adducts were separated by HPLC and their absolute configurations were assigned by circular dichroism. 1H NMR studies revealed significant differences in conformation of the tetrahydroaromatic ring between the sterically unrestricted naphthalene derivative and the sterically congested derivatives of benzo[a]pyrene and benzo[c]phenanthrene. These differences may have a bearing on the higher carcinogenicity shown by the latter hydrocarbons. Undecadeoxyoligonucleotides bearing regio- and stereochemically defined adenine N6-anti-trans-benzo[a]pyrene adducts have been prepared." @default.
- W2024901968 created "2016-06-24" @default.
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- W2024901968 date "1995-06-01" @default.
- W2024901968 modified "2023-09-23" @default.
- W2024901968 title "An efficient route to N6 deoxyadenosine adducts of diol epoxides of carcinogenic polycyclic aromatic hydrocarbons" @default.
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- W2024901968 doi "https://doi.org/10.1016/0968-0896(95)00065-o" @default.
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