Table 1.
1H (400 MHz) and 13C NMR (100 MHz) Data of Compounds 1−4 in CD3OD
| position | 1 | 2 | 3 | 4 | ||||
|---|---|---|---|---|---|---|---|---|
| δH, mult. (J in Hz) | δC | δH, mult. (J in Hz) | δC | δH, mult. (J in Hz) | δC | δH, mult. (J in Hz) | δC | |
| Erp-Trp | ||||||||
| 1 | 173.8 | 173.9 | 173.8 | 173.9 | ||||
| 2 | 4.90, dd (11.2, 4.1) | 51.8 | 4.90, dd (11.0, 4.1) | 51.8 | 4.90, dd (11.2, 4.4) | 51.8 | 4.89, dd (11.2, 4.1) | 52.0 |
| 3 | 3.16, dd (−13.2, 4.1) | 28.2 | 3.16, dd (−13.3, 4.1) | 28.2 | 3.16, dd (−13.2, 4.4) | 28.2 | 3.19, dd (−13.2, 4.1) | 28.3 |
| 3.41, dd (−13.2, 11.2) | 3.41, dd (−13.3, 11.0) | 3.41, dd (−13.2, 11.2) | 3.41, dd (−13.2, 11.2) | |||||
| 4 | 7.15, s | 125.7 | 7.16, s | 125.7 | 7.15, s | 125.4 | 7.12, s | 125.2 |
| 5 | 109.3 | 109.3 | 108.8 | 108.8 | ||||
| 6 | 130.5 | 130.4 | 130.4 | 130.4 | ||||
| 7 | 7.54, brd (7.8) | 119.5 | 7.55, brd (7.8) | 119.6 | 7.53, m | 119.4 | 7.53, m | 119.4 |
| 8 | 7.07, m | 120.6 | 7.05, m | 120.6 | 7.03, m | 120.3 | 7.04, m | 120.3 |
| 9 | 7.14, m | 122.7 | 7.13, m | 122.7 | 7.06, m | 122.1 | 7.07, m | 122.1 |
| 10 | 7.79, brd (7.3) | 114.7 | 7.80, brd (7.3) | 114.7 | 7.50, m | 115.2 | 7.51, m | 115.3 |
| 11 | 137.1 | 137.1 | 136.8 | 136.9 | ||||
| 12 | 59.2 | 59.2 | 60.1 | 60.1 | ||||
| 13 | 3.23, dd (4.1, 2.6) | 58.9 | 3.25, dd (4.1, 2.6) | 58.9 | 6.12, dd (17.5, 10.7) | 145.3 | 6.13, dd (10.7, 17.5) | 145.3 |
| 14 | 2.81, dd (−4.6, 2.6) | 45.9 | 2.82, dd (−4.6, 2.6) | 46.0 | 5.16, brd (17.5) | 114.1 | 5.17, brd (17.5) | 114.1 |
| 2.86, dd (−4.6, 4.1) | 2.87, dd (−4.6, 4.1) | 5.20, brd (10.7) | 5.21, brd (10.7) | |||||
| 15 | 1.51, s | 23.1 | 1.52, s | 23.1 | 1.70, s | 28.4 | 1.71, s | 28.4 |
| 16 | 1.67, s | 25.1 | 1.68, s | 25.1 | 1.70, s | 28.5 | 1.71, s | 28.5 |
| TrcGly | ||||||||
| 17 | 173.3 | 173.3 | 173.2 | 173.3 | ||||
| 18 | 4.60, m | 53.4 | 4.60, m | 53.4 | 4.59, m | 53.3 | 4.59, m | 53.4 |
| 19 | 2.77, m | 36.2 | 2.76, m | 36.2 | 2.79, m | 36.2 | 2.86, m | 36.1 |
| 2.49, m | 2.46, m | 2.50, m | 2.55, m | |||||
| 20 | 5.18, m | 125.2 | 5.17, m | 125.3 | 5.18, m | 125.2 | 5.19, m | 125.0 |
| 21 | 5.50, m | 131.3 | 5.50, m | 131.3 | 5.49, m | 131.3 | 5.50, m | 131.6 |
| 22 | 1.56, brd (6.2) | 18.7 | 1.57, brd (6.2) | 18.6 | 1.56, m | 18.7 | 1.57, brd (6.4) | 18.6 |
| Leu | ||||||||
| 23 | 174.0 | 173.9 | 173.9 | 174.2 | ||||
| 24 | 4.59, m | 54.9 | 4.59, m | 54.9 | 4.61, m | 54.9 | 4.56, m | 55.0 |
| 25 | 1.73~1.80, m | 44.7 | 1.76, m | 44.5 | 1.73~1.76, m | 44.7 | 1.60, m | 44.3 |
| 1.74, m | ||||||||
| 26 | 1.73, m | 25.9 | 1.75, m | 26.0 | 1.73, m | 25.9 | 1.61, m | 25.9 |
| 27 | 0.94, d (6.3) | 21.9 | 0.94, d (6.3) | 22.0 | 0.94, d (5.8) | 22.0 | 0.92, d (6.5) | 21.6 |
| 28 | 0.97, d (6.2) | 23.2 | 0.97, d (6.2) | 23.2 | 0.97, d (5.8) | 23.3 | 0.94, d (6.5) | 23.5 |
| NMeLeu | ||||||||
| 29 | 171.5 | 171.3 | 171.5 | 171.5 | ||||
| 30 | 5.05, t (7.2) | 59.8 | 4.99, t (7.0) | 60.2 | 5.05, t (7.2) | 59.7 | 4.98, dd (6.2, 8.0) | 60.1 |
| 31 | 1.84, m | 33.7 | 1.44, m | 33.9 | 1.83, m | 33.7 | 1.57, m | 38.4 |
| 2.19, m | 1.94, m | |||||||
| 32 | 1.47, m | 33.3 | 1.58, m | 33.5 | 1.47, m | 33.2 | 1.49, m | 25.7 |
| 33 | 0.92, d (6.9) | 17.3 | 0.95, d (6.9) | 17.8 | 0.92, d (6.9) | 17.3 | 0.97, d (6.6) | 23.0 |
| 34 | 3.33, m | 68.4 | 3.40, m | 68.3 | 3.33, m | 68.4 | 0.97, d (6.6) | 23.5 |
| 3.45, m | 3.47, m | 3.45, m | ||||||
| N-Me | 2.74, s | 29.7 | 2.75, s | 29.8 | 2.74, s | 29.7 | 2.73, s | 30.0 |
| Ala | ||||||||
| 35 | 175.1 | 175.0 | 175.0 | 175.3 | ||||
| 36 | 4.83, q (6.9) | 46.7 | 4.87, q (6.9) | 46.8 | 4.83, q (6.9) | 46.7 | 4.85, q (6.8) | 46.7 |
| 37 | 1.24, d (6.9) | 17.1 | 1.25, d (6.9) | 17.0 | 1.24, d (6.9) | 17.2 | 1.27, d (6.8) | 17.3 |
| mNO2-Tyr | ||||||||
| 38 | 172.3 | 172.3 | 172.3 | 173.2 | ||||
| 39 | 4.58, m | 55.5 | 4.59, m | 55.4 | 4.59, m | 55.5 | 4.59, m | 55.6 |
| 40 | 3.04, dd (−13.1, 9.9) | 38.2 | 3.04, dd (−13.1, 9.9) | 38.2 | 3.04, dd (−13.1, 9.8) | 38.2 | 2.99, dd (−13.3, 9.0) | 38.8 |
| 2.72, m | 2.72, m | 2.71, m | 2.58, m | |||||
| 41 | 129.5 | 129.5 | 129.5 | 128.3 | ||||
| 42 | 7.79, d (2.2) | 126.7 | 7.79, d (2.2) | 126.8 | 7.78, d (2.2) | 126.7 | 6.93, m | 131.3 |
| 43 | 135.5 | 135.5 | 135.4 | 6.66, m | 116.3 | |||
| 44 | 154.6 | 154.6 | 154.6 | 157.3 | ||||
| 45 | 7.05, d (8.6) | 121.1 | 7.05, d (8.6) | 121.1 | 7.06, d (8.6) | 121.1 | 6.66, m | 116.3 |
| 46 | 7.41, dd (8.6, 2.2) | 139.2 | 7.41, dd (8.6, 2.2) | 139.2 | 7.40, dd (8.6, 2.2) | 139.2 | 6.93, m | 131.3 |
| NMeLeu | ||||||||
| 47 | 169.6 | 169.6 | 169.6 | 169.4 | ||||
| 48 | 4.66, dd (11.6, 3.2) | 59.7 | 4.67, dd (11.6, 3.4) | 59.7 | 4.67, dd (11.7, 3.0) | 59.7 | 4.63, m | 59.9 |
| 49 | 1.64, m | 38.4 | 1.62, m | 38.4 | 1.61, m | 38.4 | 1.58, m | 38.4 |
| −0.67, m | −0.66, m | −0.67, m | −0.69, m | |||||
| 50 | 1.08, m | 25.4 | 1.06, m | 25.4 | 1.08, m | 25.4 | 1.08, m | 25.4 |
| 51 | 0.16, d (6.7) | 21.0 | 0.17, d (6.7) | 21.0 | 0.17, d (6.7) | 21.0 | 0.16, d (6.6) | 21.0 |
| 52 | 0.37, d (6.7) | 23.5 | 0.37, d (6.7) | 23.5 | 0.38, d (6.7) | 23.5 | 0.37, d (6.6) | 23.5 |
| N-Me | 2.68, s | 29.8 | 2.68, s | 29.9 | 2.68, s | 29.8 | 2.58, s | 29.9 |