Table 1.
NMR-spectroscopic data of petrocidin A (1) in MeOD-d4 and DMSO-d6 (1H: 600 MHz; 13C: 150 MHz).
| Position | δC, Type | δH (J, Hz) | COSY | HMBC a | HMBC b |
|---|---|---|---|---|---|
| 1 | 114.7, C | - | - | - | - |
| 2 | 151.7, C | - | - | - | - |
| 3 | 147.0, C | - | - | - | - |
| 4 | 121.3, CH | 6.98 (1H, d, J = 7.8 Hz) | 6.71 | 151.7, 147.0, 121.9 | - |
| 5 | 119.6, CH | 6.71 (1H, t, J = 7.8 Hz) | 6.98, 7.34 | 147.0, 114.7, 121.3 | - |
| 6 | 121.9, CH | 7.34 (1H, d, J = 7.8 Hz) | 6.71 | 174.2, 151.7, 121.3 | - |
| 7 | 174.2, C | - | - | - | - |
| Orn | - | - | - | - | - |
| CO | 172.8, C | - | - | - | - |
| α | 60.3, CH | 4.26 (1H, t, J = 8.5 Hz) | 2.30, 2.01 | 172.8, 29.1, 23.7 | - |
| β | 29.1, CH2 | 2.30 (1H, m), 2.01 (1H, m) | 2.02, 1.94 | 46.4, 23.7, 60.3, 172.8 | 171.9 (C-7) |
| γ | 23.7, CH2 | 2.02 (1H, m), 1.94 (1H, m) | 2.30, 2.01, 2.02, 1.94 | 29.1, 60.3, 46.4 | - |
| δ | 46.4, CH2 | 3.51 (2H, t, J = 4.7 Hz) | 2.02, 1.94 | 168.9, 29.1, 23.7 | - |
| Leu | - | - | - | - | - |
| NH | - | 8.02 (1H, s, DMSO-d6) | - | - | 37.8 (Leu β-C), 52.6 (Leu α-C), 58.5 (Orn α-C), 166.6 (Leu CO) |
| CO | 168.9, C | - | - | - | - |
| α | 54.6, CH | 4.13 (1H, t, J = 5.6 Hz) | 1.91, 1.52 | 168.9, 39.4, 25.8 | - |
| β | 39.4, CH2 | 1.52 (1H, m), 1.91 (1H, m) | 1.89, 4.13 | 168.9, 54.6, 25.8, 23.2, 22.2 | - |
| γ | 25.8, CH | 1.89 (1H, m) | 0.96, 0.95, 1.52, 1.91 | 39.4 | - |
| δ | 22.2, 23.2, CH3 | 0.96 (3H, d, J = 6.5 Hz) | 1.89 | 25.8, 39.4 | - |
| 0.95 (3H, d, J = 3.1, 6.2 Hz) |
a HMBC correlations, optimized for 8.3 Hz in MeOD-d4, are from protons stated to the indicated carbon; b HMBC correlations, optimized for 8.3 Hz in DMSO-d6, are from protons stated to the indicated carbon.