Table 1.
1H (400 MHz) and 13C (100 MHz) NMR data for 1 and 2 in pyridine-d5.
| 1 | 2 | ||||||
|---|---|---|---|---|---|---|---|
| Unit | No. | δ C | δ H | Unit | No. | δ C | δ H |
| N-O-DiMe Glu | 1 | 170.0, C | N-Me Glu | 1 | 170.1, C | ||
| 2 | 62.8, CH | 4.37, dd (8.4, 4.6) | 2 | 63.0, CH | 4.44, dd (8.4, 4.7) | ||
| 3 | 24.7, CH2 | 2.85, m; 2.67, m | 3 | 24.9, CH2 | 2.95, m; 2.80, m | ||
| 4 | 30.5, CH2 | 2.70, m | 4 | 30.9, CH2 | 2.82, m | ||
| 5 | 173.2, C | 5 | 175.4, C | ||||
| NMe | 38.9, CH3 | 3.52, s | NMe | 38.9, CH3 | 3.55, s | ||
| OMe | 51.5, CH3 | 3.62, s | |||||
| Val | 1 | 173.3, C | Val | 1 | 173.3, C | ||
| 2 | 55.1, CH | 4.94, t (10.0) | 2 | 55.1, CH | 4.95, t (10.1) | ||
| 3 | 31.7, CH | 2.40, m | 3 | 31.7, CH | 2.41, m | ||
| 4 | 18.2, CH3 | 1.09, d (6.5) | 4 | 18.2, CH3 | 1.08, d (6.6) | ||
| 5 | 19.3, CH3 | 0.89, d (6.5) | 5 | 19.4, CH3 | 0.93, d (6.6) | ||
| NH | 9.23, d (10.0) | NH | 9.26, d (10.1) | ||||
| Pip | 1 | 172.8, C | Pip | 1 | 172.7, C | ||
| 2 | 52.9, CH | 5.54, br. d (4.3) | 2 | 52.9, CH | 5.51, overlapped | ||
| 3 | 28.0, CH2 | 2.14, m; 1.55, m | 3 | 28.0, CH2 | 2.15, m; 1.51, m | ||
| 4 | 19.9, CH2 | 1.35, m | 4 | 19.9, CH2 | 1.35, m | ||
| 5 | 24.8, CH2 | 1.59, m; 1.08, m | 5 | 24.7, CH2 | 1.58, m; 1.05, m | ||
| 6 | 43.8, CH2 | 3.77, m | 6 | 43.7, CH2 | 3.74, m | ||
| Ile | 1 | 171.2, b C | Ile | 1 | 171.2, d C | ||
| 2 | 53.7, CH | 5.22, br. d (8.2) | 2 | 53.7, CH | 5.20, br. d (8.0) | ||
| 3 | 36.8, CH | 2.05, m | 3 | 36.7, CH | 2.04, m | ||
| 4 | 23.0, CH2 | 1.59, m; 1.03, m | 4 | 22.9, CH2 | 1.57, m; 1.01, m | ||
| 5 | 11.7, CH3 | 0.95, t (6.8) | 5 | 11.7, CH3 | 0.95, t (6.8) | ||
| 3-Me | 16.5, CH3 | 1.11, d (6.7) | 3-Me | 16.5, CH3 | 1.13, d (6.7) | ||
| NH | 6.74, d (8.2) | NH | 6.72, d (8.3) | ||||
| N-Me Gln | 1 | 169.6, C | N-O-DiMe Glu | 1 | 169.3, C | ||
| 2 | 59.9, CH | 5.60, t (6.7) | 2 | 59.4, CH | 5.45, t (7.2) | ||
| 3 | 25.3, CH2 | 2.76, m; 2.40, m | 3 | 24.4, CH2 | 2.69, m; 2.19, m | ||
| 4 | 32.0, CH2 | 2.64, m | 4 | 30.3, CH2 | 2.60, m | ||
| 5 | 174.8, C | 5 | 172.9, C | ||||
| NMe | 29.7, CH3 | 3.00, s | NMe | 29.7, CH3 | 3.00, s | ||
| 5-NH2 | 7.65, s; 8.29, s | OMe | 51.5, CH3 | 3.65, s | |||
| N-Me Val | 1 | 170.7, C | N-Me Val | 1 | 170.5, C | ||
| 2 | 57.9, CH | 5.63, d (10.5) | 2 | 57.9, CH | 5.52, overlapped | ||
| 3 | 28.0, CH | 2.52, m | 3 | 28.1, CH | 2.55, m | ||
| 4 | 18.1, CH3 | 0.73, d (6.5) | 4 | 18.1, CH3 | 0.78, d (6.5) | ||
| 5 | 19.3, CH3 | 0.99, d (6.5) | 5 | 19.2, CH3 | 1.03, d (6.5) | ||
| NMe | 28.7, CH3 | 3.19, s | NMe | 28.7, CH3 | 3.19, s | ||
| Gly | 1 | 171.1, b C | Gly | 1 | 171.1, d C | ||
| 2 | 42.5, CH2 | 5.08, dd (17.4, 7.8)4.77, d (17.4) | 2 | 42.5, CH2 | 5.09, dd (17.4, 7.9)4.78, d (17.4) | ||
| NH | 8.57, d (7.8) | NH | 8.57. d (7.9) | ||||
| Pro | 1 | 171.4, a C | Pro | 1 | 171.3, c C | ||
| 2 | 60.9, CH | 4.89, dd (7.2, 5.1) | 2 | 60.8, CH | 4.89, dd (7.3, 5.1) | ||
| 3 | 29.6, CH2 | 2.11, m; 2.03, m | 3 | 29.5, CH2 | 2.10, m; 1.99, m | ||
| 4 | 25.2, CH2 | 2.09, m; 1.69, m | 4 | 25.2, CH2 | 2.08, m; 1.69, m | ||
| 5 | 47.6, CH2 | 3.87, m | 5 | 47.5, CH2 | 3.85, m | ||
| Phe | 1 | 171.4, a C | Phe | 1 | 171.3, c C | ||
| 2 | 53.4, CH | 5.34, t (10.6) | 2 | 53.4, CH | 5.35, td (8.8, 4.0) | ||
| 3 | 37.6, CH2 | 3.52, overlapped | 3 | 37.6, CH2 | 3.53, overlapped | ||
| 4 | 138.2, C | 4 | 138.2, C | ||||
| 5, 9 | 129.9, CH | 7.67, d (7.5) | 5, 9 | 129.9, CH | 7.69, d (7.5) | ||
| 6, 8 | 128.6, CH | 7.41, t (7.5) | 6, 8 | 128.6, CH | 7.42, d (7.5) | ||
| 7 | 126.8, CH | 7.24, t (7.5) | 7 | 126.8, CH | 7.24, d (7.5) | ||
| NH | 8.06, d (8.7) | NH | 8.09, d (8.8) | ||||
| Hmp | 1 | 169.1, C | Hmp | 1 | 169.1, C | ||
| 2 | 75.6, CH | 5.52, br. s | 2 | 75.6, CH | 5.54, d (1.5) | ||
| 3 | 36.4, CH | 2.31, m | 3 | 36.4, CH | 2.32, m | ||
| 4 | 26.1, CH2 | 1.15, m | 4 | 26.1, CH2 | 1.18, m | ||
| 5 | 11.6, CH3 | 0.70, t (7.3) | 5 | 11.6, CH3 | 0.72, (7.4) | ||
| 3-Me | 14.4, CH3 | 0.88, d (6.5) | 3-Me | 14.4, CH3 | 0.89, d (6.7) | ||
a–d These carbon signals are interchangeable.