Activated Fjord-Region Metabolites of Dibenzo[a,l]pyrene: Synthesis and Mutagenic Activities of the Diastereomeric syn− and anti−11,12-Dihydrodiol 13,14-Epoxides

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• Analytical data for syn-DB[a,l]PDE 10 were as follows: UV, λmax (nm, ε [cm2mmol−1]) 207 (36,300) 226 (22,400) 240 (24,400) 271 (25,400) 282 (30,400) 294 (34,000) 325 (16,200) 340 (21,300); 400 MHz 1H-NMR (DMSO-d6/acetone-d6/D2O), δ 3.98 (dd, 1H, H12, J12,13 = 1.9 Hz), 4.03 (dd, 1H, H13), 4.47 (d, 1H, H14, J13,14 = 4.2 Hz), 4.87 (d, 1H, H11, J11,12 = 8.6 Hz), 7.33–7.86 (m, 2H, H2, H3), 8.09 (pseudo-t, 1H, H6), 8.16 (s, 2H, H8, H9), 8.29 (d, 1H, H7, J6,7 = 7.6 Hz), 8.49 (s, 1H, H10), 9.04 (d, 1H, H4, J3,4 = 9.0 Hz), 9.06 (d, 1H, H5, J5,6 = 8.2 Hz), 9.18 (d, 1H, H1, J1,2 = 8.4 Hz); MS (m/z, relative abundance) 353 (23%, MH+), 352 (100%, M+), 335 (17%, MH+-H2O), 334 (83%, M+-H2O). Analytical data for anti-DB[a,l]PDE 11 were as follows: UV, λmax (nm, ε [cm2mmol−1]) 208 (47,600) 225 (26,600) 241 (30,600) 262 (28,200) 272 (31,000) 295 (36,500) 327 (19,900) 342 (25,100); 400 MHz 1H-NMR (DMSO-d6/acetone-d6,/D2O), δ 3.83 (dd, 1H, H13), 3.93 (dd, 1H, H12, J12,13 = 1.4 Hz), 4.81 (d, 1H, H14, J13,14 = 4.3 Hz), 5.07 (d, 1H, H11, J11,12 = 9.1 Hz), 7.72–7.74 (m, 1H, H2), 7.78–7.80 (m, 1H, H3), 8.05 (pseudo-t, 1H, H6), 8.13 (s, 2H, H8, H9), 8.26 (dd, 1H, H7, J6,7 = 7.5 Hz), 8.51 (bs, 1H, H10), 8.74 (dd, 1H, H1, J1,2 = 8.1 Hz, J1,3 = 1.0 Hz), 8.95 (d, 1H, H4, J3,4 = 8.0 Hz), 9.00 (d, 1H, H5, J5,6 = 7.7 Hz); MS (m/z, relative abundance) 353 (5%, MH+), 352 (20%, M+), 335 (30%, MH+-H2O), 334 (100%, M+-H2O).
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