1H NMR data of glafenine, 5-hydroxyglafenine (M3), and its GSH conjugate (M1) (δ in CD3OD)
Refer to Fig. 6 for signal assignments of the thioether moiety; cysteine 1″–H: δ 3.3/3.4, cysteine 2″–H: δ 4.4, glutamate 3″–H: δ 2.5, glutamate 4″–H: δ 2.1/2.3, glutamate 5″–H: δ 3.6, glycine 6″–H: δ 3.7.
| Proton Signals | |||
|---|---|---|---|
| Glafenine | M3 | M1 | |
| C3 | 7.74 (1H, bd, J = 8.2 Hz) | 7.50 (1H, d, J = 8.8 Hz) | 7.27 (1H, d, J = 8.6 Hz) |
| C4 | 7.62 (1H, ddd, J = 8.2, 7.9 and 1.8 Hz) | 7.13 (1H. dd, J = 8.8 and 2.9 Hz) | 7.10 (1H, d, J = 8.6 Hz) |
| C2′ | 8.57 (1H, d, J = 5.4 Hz) | 8.41 (1H, d, J = 5.8 Hz) | 8.33 (1H, d, J = 6.2 Hz) |
| C3′ | 7.41 (1H, d, J = 5.4 Hz) | 6.93 (1H, d, J = 5.8 Hz) | 6.36 (1H, d, J = 6.2 Hz) |
| C5′ | 8.20 (1H, d, J = 9.0 Hz) | 8.28 (1H, d, J = 9.0 Hz) | 8.46 (1H, d, J = 9.0 Hz) |
| C6′ | 7.60 (1H, dd, J = 9.0 and 2.1 Hz) | 7.60 (1H, dd, J = 9.0 and 1.9 Hz) | 7.60 (1H, dd, J = 9.0 and 2.0 Hz) |
| C8′ | 7.94 (1H, d, J = 2.1 Hz) | 7.89 (1H, d, J = 1.9 Hz) | 7.87 (1H, d, J = 2.0 Hz) |
| C6 | 8.19 (1H, dd, J = 8.1 and 1.8 Hz) | 7.57 (1H, d, J = 2.9 Hz) | |
| C5 | 7.16 (1H, bdd, J = 8.1 and 7.9 Hz) | ||