1H NMR and 13C NMR data of NBP, 3-hydroxy-NBP, 10-hydroxy-NBP, NBP-11-oic acid, 10-keto-NBP, 11- hydroxy-NBP, and 3-N-acetylcysteine-NBP
| Position | NBP | 3-Hydroxy-NBP | 10-Hydroxy-NBP | NBP-11-Oic Acid | 10-Keto-NBP | 11-Hydroxy-NBP | 3-N -Acetylcysteine-NBP* | |||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| δC | δH(J/Hz) | δC | δH(J/Hz) | δC | δH(J/Hz) | δC | δH(J/Hz) | δC | δH(J/Hz) | δC | δH(J/Hz) | δC | δH(J/Hz) | |
| 1 | 170.7 | 168.4 | 172.8 | 175.1 | 172.9 | 172.9 | 170.5 | |||||||
| 2 | ||||||||||||||
| 3 | 81.4 | 5.47(1H, dd, 7.9, 4.1) | 107.5 | 83.1 | 5.66(1H, dd, 7.6, 3.9) | 85.5 | 5.61(1H, dd, 6.8, 3.9) | 82.8 | 5.60(1H, dd, 8.0, 3.1) | 83.8 | 5.60(1H, dd, 7.7, 3.9) | 96.7 | ||
| 4 | 125.6 | 7.43(1H, dd, 7.7, 0.7) | 125.5 | 7.57(1H, m) | 126.2 | 7.59(1H, m) | 128.7 | 7.59(1H, m) | 126.8 | 7.60(1H, m) | 126.7 | 7.58(1H, m) | 126.2 | 7.56(1H, m) |
| 5 | 129.0 | 7.67(1H, td, 7.5, 1.0) | 130.5 | 7.70(1H, t, 6.7) | 130.4 | 7.79(1H, t, 7.5) | 133.5 | 7.76(1H, td, 7.6, 1.0) | 131.0 | 7.76(1H, t, 7.3) | 130.8 | 7.75(1H, td, 7.7, 1.1) | 131.3 | 7.75(1H, m) |
| 6 | 121.7 | 7.52(1H, t, 7.5) | 122.2 | 7.57(1H, m) | 123.4 | 7.62(1H, t) | 125.9 | 7.59(1H, m) | 124.0 | 7.62(1H, m) | 123.9 | 7.58(1H, m) | 123.9 | 7.61(1H, m) |
| 7 | 133.9 | 7.89(1H, d, 7.7) | 134.6 | 7.86(1H, t, 11.9) | 135.6 | 7.87(1H, d, 7.6) | 138.1 | 7.85(1H, d, 7.6) | 136.2 | 7.85(1H, d, 7.5) | 136.1 | 7.84(1H, d, 7.7) | 136.4 | 7.85(1H, m) |
| 8 | 34.4 | 2.06(1H, m) | 38.6 | 2.21(1H, m) | 34.8 | 2.18(1H, m) | 37.1 | 2.17(1H, m) | 30.0 | 2.42(1H, m) | 35.9 | 2.14(1H, m) | 31.5 | 2.15(2H, m) |
| 1.76(1H, m) | 2.08(1H, m) | 1.91(1H, m) | 1.75(1H, m) | 1.90(1H, m) | 1.77(1H, m) | |||||||||
| 9 | 26.8 | 25.3 | 31.8 | 1.59(1H, m) | 24.0 | 39.6 | 2.71(1H, m) | 22.8 | 27.0 | |||||
| 1.42(4H, m) | 1.29(4H, m) | 1.46(1H, m) | 1.70(2H, m) | 2.58(1H, m) | 1.52(4H, m) | 1.24(4H, m) | ||||||||
| 10 | 22.4 | 22.4 | 67.9 | 3.80(1H, m) | 37.4 | 2.37(2H, t, 6.8) | 210.6 | 33.7 | 23.3 | |||||
| 11 | 13.9 | 0.90(3H,t) | 13.8 | 0.86(3H, t, 7.2) | 23.5 | 1.20(3H, d, 6.2) | 179.8 | 30.4 | 2.13(3H, s) | 63.1 | 3.54(2H, t, 6.2) | 14.1 | 0.78(3H, t, 7.2) | |
| 12 | 151.4 | 148.8 | 151.8 | 154.1 | 151.8 | 152.3 | 151.3 | |||||||
| 13 | 126.1 | 126.7 | 127.0 | 129.4 | 127.4 | 127.5 | 127.5 | |||||||
d, double; H, hydrogen atom; m, multiple; NMR, nuclear magnetic resonance; t, triplet.
↵* Chemical shifts of the N-acetylcysteine moiety are not shown.