TABLE 2.
NMR analysis of the compounds formed in biotransformation experiments
| Substrate | Chemical shifts (δ)a
|
Identification | |
|---|---|---|---|
| 1H NMR | 13C NMR | ||
| Xanthene | 7.27 (H-6′, d, J = 7.5 Hz), 7.09 (H-4′, t, J = 7.5 Hz), 6.90 (H-5′, t, J = 7.5 Hz), 6.79 (H-3′, d, J = 7.5 Hz), 6.73–6.82 (H-4,5,6), 3.90 (CH2, s) | ND | 2,2′,3-Trihydroxydiphenylmethane |
| Phenoxathiin | 7.35 (H-6′, d, J = 7.5 Hz), 7.24 (H-4′, t, J = 7.5 Hz), 6.95 (H-3′, d, J = 7.5 Hz), 6.87 (H-5′, t, J = 7.5 Hz), 6.85 (H-4,6, d, J = 8.0 Hz), 6.74 (H-5, t, J = 8.0 Hz) | 155.8, 144.0, 143.4, 134.6, 130.9, 125.0, 121.6, 121.3, 119.4, 118.7, 116.0, 115.8 | 2,2′,3-Trihydroxydiphenyl sulfide |
| Dibenzothiophene | 7.98 (2H, d, J = 7.5 Hz), 7.80 (2H, d, J = 7.5 Hz), 7.59 (2H, t, J = 7.5 Hz), 7.49 (2H, t, J = 7.5 Hz) | ND | Dibenzothiophene-5-oxide |
| Naphthalene | 7.12–7.54 (H-5,6,7,8), 6.54 (H-4, d, J = 10 Hz), 6.07 (H-3, dd, J = 10 Hz, 4.5 Hz), 4.70 (H-1, d, J = 4.5 Hz), 4.39 (H-2, t, J = 4.5 Hz) | ND | cis-1,2-Dihydroxy-1,2-dihydronaphthalene |
| Anthracene | 7.45–7.98 (H-5,6,7,8,9,10), 6.73 (H-4, d, J = 9.8 Hz), 6.15 (H-3, dd, J = 9.8 Hz, 4.0 Hz), 4.87 (H-1, d, J = 4.0 Hz), 4.46 (H-2, t, J = 4.0 Hz) | ND | cis-1,2-Dihydroxy-1,2-dihydroanthracene |
| Fluoranthene | 7.70–7.73 (H-7,10), 7.60 (H-6, d, J = 7.1 Hz), 7.40–7.42 (H-4,5,8), 7.32 (H-9, t, J = 7.0 Hz), 6.65 (H-1, d, J = 4.8 Hz), 4.98 (H-3, d, J = 4.8 Hz), 4.79 (H-2, t, J = 4.8 Hz) | 141.9 (C), 138.6 (C), 136.9 (C), 135.9 (C), 134.3 (C), 132.8 (C), 129.7 (C-5), 129.3 (C-8), 127.3 (C-9), 125.1 (C-4), 122.4 (C-10), 122.1 (C-1), 120.9 (C-7), 70.1 (C-2), 69.5 (C-3) | cis-2,3-Dihydroxy-2,3-dihydrofluoranthene |
| 8.11 (H-4 or 6, d, J = 6.5 Hz), 7.95 (H-1, d, J = 7.0 Hz), 7.86 (H-3, d, J = 8.5 Hz), 7.82 (H-4 or 6, d, J = 8.5 Hz), 7.62–7.66 (H-2,5), 7.56 (H-10, d, J = 8.0 Hz), 7.26 (H-9, t, J = 8.0 Hz), 6.81 (H-8, d, J = 8.0 Hz) | ND | 7-Hydroxyfluoranthene | |
| Biphenyl | 7.55 (H-2′,6′, d, J = 4.0 Hz), 7.37 (H-3′,5′, t, J = 4.0 Hz), 7.30 (H-4′, t, J = 4.0 Hz), 6.37 (H-6, d, J = 5.5 Hz), 6.11 (H-5, m), 5.90 (H-4, d, J = 9.5 Hz), 4.61 (H-3, m), 4.51 (H-2, d, J = 6.0 Hz) | ND | cis-2,3-Dihydroxy-2,3-dihydrobiphenyl |
a
Determined at 500 MHz (1H NMR) or 125 MHz (13C NMR) in CDCl3. Chemical shift multiplicities are abbreviated as follows: s, singlet; d, doublet; t, triplet; m, multiplet; dd, doublet of doublets. (C), 13C chemical shifts of quaternary carbons; ND, not determined.