Effect of a peri fluoro substituent on the conformation of dihydrodiol derivatives of polycyclic aromatic hydrocarbons
Chiu P-L; Fu, PP; Yang, SK
| HERO ID | 2136482 |
|---|---|
| In Press | No |
| Year | 1982 |
| Title | Effect of a peri fluoro substituent on the conformation of dihydrodiol derivatives of polycyclic aromatic hydrocarbons |
| Authors | Chiu P-L; Fu, PP; Yang, SK |
| Journal | Biochemical and Biophysical Research Communications |
| Volume | 106 |
| Issue | 4 |
| Page Numbers | 1405-1411 |
| Abstract | HEEP COPYRIGHT: BIOL ABS. trans-3,4-, 5,6-, 8,9-, and 10,11-dihydrodiols formed from the metabolism of 7-fluorobenz(a)anthracene by rat liver microsomes were isolated by reversed-phase high performance liquid chromatography. UV absorption, mass, and NMR spectral analyses indicated that the 5,6- and 8,9-dihydrodiols were preferentially in quasi-diaxial conformations, whereas the 3,4- and 10,11-dihydrodiols were preferentially in quasi-diequatorial conformations. CPK (Cory-Pauling-Koltun) space-filling models suggest that the quasi-diaxial conformation is primarily the result of electronic repulsion between the fluorine and the peri hydroxyl oxygen. These findings provide a structural basis in the interpretation of the carcinogenic potencies of some fluorinated polycyclic aromatic hydrocarbons. |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |