Synthesis and structure determination of the adducts of dibenzo[a,f]pyrene diol epoxides and deoxyadenosine or deoxyguanosine

Kai Ming Li, N. V S Ramakr1Shna, Ercole Cavalieri, Eleanor G Rogan, N. S. Padmavathi

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

(±)-5yn-dibenzo[a, l]pyrene diol epoxide (DB[a,l]PDE) and (+)-anti-DB[a,[]?DE were reacted with deoxyadenosine (dA) or deoxyguanosine (dG) in dimethylformamide at 100 °C for 30 min. The crude products were purified by reverse phase HPLC under gradient and isocratic conditions. The structure of each adduct was assigned by 1D and 2D NMR spectra and by fast atom bombardment mass spectrometry. Five adducts were isolated from the reaction of (±)-s)w-DB[a,/]PDE and dA: yy/j-DBta^PDE-N^A-1,. syn-DB[fl,/]PDE-N6dA-2,. yy/z-DB[a,/]PDE-N6dA-3,. yjw-DBfoqPDE-NftiA^ and. yytf-DB[a,/]PDE-N7Ade. Four adducts were isolated from the reaction of (±)-anti-DB[a,{]PDE and dA: anri-DB[a,f]PDE-^6A~, anti-DB[a,/]PDE-N6d A-2, fl/7//-DB[tf,/]PDE-N6dA~3 and tfAW-DB[r/,/]PDE-N6dA-4. Two adducts were isolated from the reaction of (±)-.vy/?-DB[fl,/]PDE and dG: (±)-11,12, n-trihydroxy-tetrahydroDBtcG/JP-M-NfdG and (±)-11,12,13-trihydroxy-tetrahydroDB[a,/]P-14-N7Gua. Two adducts were isolated from the reaction of {±yanri-DB[a>l]PDE and dG: (±)-11,12,13-trihydroxy-tetra-hydroDB[a,/]P-14-N2dG and (±)-11, ^O-trihydroxy-tetrahydroDB^/lP-M-^Gua.

Original languageEnglish (US)
Pages (from-to)207-213
Number of pages7
JournalPolycyclic Aromatic Compounds
Volume6
Issue number1-4
DOIs
StatePublished - Jan 1 1994

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Deoxyguanosine
Epoxy Compounds
Pyrene
Dimethylformamide
Mass spectrometry
Nuclear magnetic resonance
Atoms
pyrene
2'-deoxyadenosine

Keywords

  • Dibenzo[a,l]
  • pyrene diol epoxides deoxyribonucleoside adducts synthesis structure determination

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Cite this

Synthesis and structure determination of the adducts of dibenzo[a,f]pyrene diol epoxides and deoxyadenosine or deoxyguanosine. / Li, Kai Ming; Ramakr1Shna, N. V S; Cavalieri, Ercole; Rogan, Eleanor G; Padmavathi, N. S.

In: Polycyclic Aromatic Compounds, Vol. 6, No. 1-4, 01.01.1994, p. 207-213.

Research output: Contribution to journalArticle

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abstract = "(±)-5yn-dibenzo[a, l]pyrene diol epoxide (DB[a,l]PDE) and (+)-anti-DB[a,[]?DE were reacted with deoxyadenosine (dA) or deoxyguanosine (dG) in dimethylformamide at 100 °C for 30 min. The crude products were purified by reverse phase HPLC under gradient and isocratic conditions. The structure of each adduct was assigned by 1D and 2D NMR spectra and by fast atom bombardment mass spectrometry. Five adducts were isolated from the reaction of (±)-s)w-DB[a,/]PDE and dA: yy/j-DBta^PDE-N^A-1,. syn-DB[fl,/]PDE-N6dA-2,. yy/z-DB[a,/]PDE-N6dA-3,. yjw-DBfoqPDE-NftiA^ and. yytf-DB[a,/]PDE-N7Ade. Four adducts were isolated from the reaction of (±)-anti-DB[a,{]PDE and dA: anri-DB[a,f]PDE-^6A~, anti-DB[a,/]PDE-N6d A-2, fl/7//-DB[tf,/]PDE-N6dA~3 and tfAW-DB[r/,/]PDE-N6dA-4. Two adducts were isolated from the reaction of (±)-.vy/?-DB[fl,/]PDE and dG: (±)-11,12, n-trihydroxy-tetrahydroDBtcG/JP-M-NfdG and (±)-11,12,13-trihydroxy-tetrahydroDB[a,/]P-14-N7Gua. Two adducts were isolated from the reaction of {±yanri-DB[a>l]PDE and dG: (±)-11,12,13-trihydroxy-tetra-hydroDB[a,/]P-14-N2dG and (±)-11, ^O-trihydroxy-tetrahydroDB^/lP-M-^Gua.",
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T1 - Synthesis and structure determination of the adducts of dibenzo[a,f]pyrene diol epoxides and deoxyadenosine or deoxyguanosine

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AU - Ramakr1Shna, N. V S

AU - Cavalieri, Ercole

AU - Rogan, Eleanor G

AU - Padmavathi, N. S.

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N2 - (±)-5yn-dibenzo[a, l]pyrene diol epoxide (DB[a,l]PDE) and (+)-anti-DB[a,[]?DE were reacted with deoxyadenosine (dA) or deoxyguanosine (dG) in dimethylformamide at 100 °C for 30 min. The crude products were purified by reverse phase HPLC under gradient and isocratic conditions. The structure of each adduct was assigned by 1D and 2D NMR spectra and by fast atom bombardment mass spectrometry. Five adducts were isolated from the reaction of (±)-s)w-DB[a,/]PDE and dA: yy/j-DBta^PDE-N^A-1,. syn-DB[fl,/]PDE-N6dA-2,. yy/z-DB[a,/]PDE-N6dA-3,. yjw-DBfoqPDE-NftiA^ and. yytf-DB[a,/]PDE-N7Ade. Four adducts were isolated from the reaction of (±)-anti-DB[a,{]PDE and dA: anri-DB[a,f]PDE-^6A~, anti-DB[a,/]PDE-N6d A-2, fl/7//-DB[tf,/]PDE-N6dA~3 and tfAW-DB[r/,/]PDE-N6dA-4. Two adducts were isolated from the reaction of (±)-.vy/?-DB[fl,/]PDE and dG: (±)-11,12, n-trihydroxy-tetrahydroDBtcG/JP-M-NfdG and (±)-11,12,13-trihydroxy-tetrahydroDB[a,/]P-14-N7Gua. Two adducts were isolated from the reaction of {±yanri-DB[a>l]PDE and dG: (±)-11,12,13-trihydroxy-tetra-hydroDB[a,/]P-14-N2dG and (±)-11, ^O-trihydroxy-tetrahydroDB^/lP-M-^Gua.

AB - (±)-5yn-dibenzo[a, l]pyrene diol epoxide (DB[a,l]PDE) and (+)-anti-DB[a,[]?DE were reacted with deoxyadenosine (dA) or deoxyguanosine (dG) in dimethylformamide at 100 °C for 30 min. The crude products were purified by reverse phase HPLC under gradient and isocratic conditions. The structure of each adduct was assigned by 1D and 2D NMR spectra and by fast atom bombardment mass spectrometry. Five adducts were isolated from the reaction of (±)-s)w-DB[a,/]PDE and dA: yy/j-DBta^PDE-N^A-1,. syn-DB[fl,/]PDE-N6dA-2,. yy/z-DB[a,/]PDE-N6dA-3,. yjw-DBfoqPDE-NftiA^ and. yytf-DB[a,/]PDE-N7Ade. Four adducts were isolated from the reaction of (±)-anti-DB[a,{]PDE and dA: anri-DB[a,f]PDE-^6A~, anti-DB[a,/]PDE-N6d A-2, fl/7//-DB[tf,/]PDE-N6dA~3 and tfAW-DB[r/,/]PDE-N6dA-4. Two adducts were isolated from the reaction of (±)-.vy/?-DB[fl,/]PDE and dG: (±)-11,12, n-trihydroxy-tetrahydroDBtcG/JP-M-NfdG and (±)-11,12,13-trihydroxy-tetrahydroDB[a,/]P-14-N7Gua. Two adducts were isolated from the reaction of {±yanri-DB[a>l]PDE and dG: (±)-11,12,13-trihydroxy-tetra-hydroDB[a,/]P-14-N2dG and (±)-11, ^O-trihydroxy-tetrahydroDB^/lP-M-^Gua.

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