Table 1.
NMR Data for Symplocamide A (1) Acquired in DMSO-d6
| position | δH (J in Hz)a | δC, mult.b | HMBC |
|---|---|---|---|
| Val 1 | 172.3, qC | ||
| 2 | 4.67, m | 56.2, CH | Val-1, Val-3, Val-4, Val-5 |
| 3 | 2.04, m | 30.7, CH | Val-2, Val-4, Val-5 |
| 4 | 0.86, d (7.0) | 19.3, CH3 | Val-2, Val-3, Val-5 |
| 5 | 0.74, d (7.0) | 17.6, CH3 | Val-2, Val-3, Val-4 |
| NH | 7.65, d (10.2) | Btyr-1 | |
| Btyr 1 | 169.0, qC | ||
| 2 | 5.05, dd (11.1, 2.7) | 60.4, CH | Btyr-1, Btyr-3, Btyr-NMe |
| 3 | 2.77, dd (11.1, 14.8) | 32.8, CH2 | Btyr-4, Btyr-5 |
| 3′ | 3.21 dd (14.8, 2.7) | 32.8, CH2 | Btyr-4, Btyr-5 |
| 4 | 131.3, qC | ||
| 5 | 7.19, dd (1.8, 8.4) | 130.1, CHx | Btyr-3, Btyr-6, Btyr-7, Btyr-9 |
| 6 | 7.02, d (8.4) | 113.0, CH | Btyr-5, Btyr-7, Btyr-8 |
| 7 | 154.5, qC | ||
| 8 | 111.0, qC | ||
| 9 | 7.39, d (1.8) | 133.6, CH | Btyr-3, Btyr-4, Btyr-7, Btyr-8 |
| OMe | 3.76, s | 56.3, CH3 | Btyr-7 |
| NMe | 2.73, s | 30.2, CH3 | Ile-1, Btyr-2 |
| Ile 1 | 169.7, qC | ||
| 2 | 4.37, m | 54.2, CH | Ahp-5, Ile-3, Ile-6 |
| 3 | 1.79, m | 33.0, CH | |
| 4 | 1.09, m | 23.7, CH2 | Ahp-5, Ile-2 |
| 5 | 0.62, m | 10.3, CH3 | Ile-3, Ile-4 |
| 6 | −0.16, d (6.7) | 13.8, CH3 | Ile-2, Ile-3, Ile-4 |
| Ahp 1 | 168.8, qC | ||
| 2 | 4.44, m | 48.9, CH | Ahp-1, Ahp-3 |
| 3 | 1.74/2.57, m | 21.8, CH2 | |
| 4 | 1.74, m | 29.7, CH2 | |
| 5 | 4.91, bs | 74.0, CH | Ahp-1, Ile-2 |
| OH | 6.14, bs | ||
| NH | 7.33, d (9.3) | Cit-1 | |
| Cit 1 | 170.2, qC | ||
| 2 | 4.24, ddd (4.0, 9.4, 9.4) | 52.4, CH | |
| 3 | 1.42/1.95, m/m | 27.6, CH2 | |
| 4 | 1.34, m | 26.6, CH2 | Cit-2, Cit-5 |
| 5 | 2.92, dt (6.0, 6.3) | 38.9, CH2 | Cit-3, Cit-4, Cit-6 |
| NH′ | 5.99, bt (6.0) | ||
| 6 | 158.7, qC | ||
| NH2 | 5.37, bs | ||
| NH | 8.51, d (7.9) | Thr-1, Cit-2 | |
| Thr 1 | 169.0, qC | ||
| 2 | 4.63, m | 54.8, CH | Gln-1, Thr-1, Thr-3 |
| 3 | 5.50, q (6.3) | 71.9, CH | Val-1, Thr-1, Thr-4 |
| 4 | 1.20, d (6.7) | 17.7, CH3 | Thr-2, Thr-3 |
| NH | 7.84, d (9.3) | Gln-1 | |
| Gln 1 | 172.5, qC | ||
| 2 | 4.37, m | 52.0, CH | But-1, Gln-1, Gln-3 |
| 3 | 1.72/1.89, m/m | 27.3, CH2 | Gln-1, Gln-2, Gln-4, Gln-5 |
| 4 | 2.13, m | 31.5, CH2 | Gln-2, Gln-3, Gln-5 |
| 5 | 173.9, qC | ||
| NH2 | 6.75/7.29, bs/bs | Gln-4, Gln-5 | |
| NH | 8.05, d (8.0) | But-1, Gln-2, Gln-3 | |
| But 1 | 172.3, qC | ||
| 2 | 2.11, t (7.0) | 37.1, CH2 | But-1, But-3, But-4 |
| 3 | 1.52, m | 18.7, CH2 | But-1, But-2, But-4 |
| 4 | 0.86, t (7.0) | 13.6, CH3 | But-2, But-3 |
a
Recorded at 400 MHz.
b
Recorded at 100 MHz.