Table 1.
1H (700 MHz) and 13C (175 MHz) NMR Spectroscopic Data for Grassypeptolides D (1) and E (2) in CDCl3.
| unit | position | Grassypeptolide D (1) | Grassypeptolide E (2) | ||
|---|---|---|---|---|---|
| δH, mult. (J in Hz) | δC, mult. | δH, mult. (J in Hz) | δC, mult. | ||
| Maba | 1 | - | 172.4, C | - | 172.9, C |
| 2 | 2.50, dq (7.0, 6.8) | 45.6, CH | 2.51, dq (7.0, 4.5) | 45.5, CH | |
| 3 | 4.22, m | 48.5, CH | 4.23, m | 47.0, CH | |
| 4 | 1.19, d (6.7) | 19.9, CH3 | 1.10, d (7.0) | 19.3, CH3 | |
| 5 | 1.12, d (7.0) | 14.4, CH3 | 1.16, d (7.0) | 14.4, CH3 | |
| NH | 7.70, br | 6.45, d (9.9) | |||
| Thr | 6 | - | 169.3, C | - | 170.5, C |
| 7 | 4.45, (6.8, 6.1) | 59.1, CH | 3.36, dd (6.9, 3.3) | 57.0, CH | |
| 8 | 4.02, m | 69.1, CH | 3.30, m | 67.9, CH | |
| 9 | 1.22, d (6.4) | 19.7, CH3 | 0.87, d (6.5) | 19.4, CH3 | |
| OH | 4.00, br | - | |||
| NH | 6.90, d (7.3) | 6.90, d (6.9) | |||
| N-Me-Leu | 10 | - | 170.3, C | - | 170.0, C |
| 11 | 4.70, br | 57.5, CH | 5.15, t (7.7) | 54.6, CH | |
| 12a | 1.97, m | 37.2, CH2 | 1.78, m | 37.1, CH2 | |
| 12b | 1.67, m | ||||
| 13 | 1.58, m | 25.3, CH | 1.52, m | 25.3, CH | |
| 14 | 0.98, d (6.4) | 23.2, CH3 | 0.98, d (6.6) | 23.2, CH3 | |
| 15 | 0.94, d (6.5) | 22.8, CH3 | 0.93, d (6.7) | 22.4, CH3 | |
| 16 | 3.20, s | 33.2, CH3 | 3.49, s | 30.7, CH3 | |
| Aba-thn-ca | 17 | - | 170.4, C | - | 169.3, C |
| 18 | 5.29, m | 78.1, CH | 5.07, m | 75.9, CH | |
| 19a | 3.60, m | 33.3, CH2 | 4.15, br dd | 35.5, CH2 | |
| 19b | 3.26, m | 3.44, dd (−11.2, 8.5) | |||
| 20 | - | 178.0, C | - | 175.0, C | |
| 21 | 4.55, m | 54.2, CH | 4.71, ddd (9.0, 4.0, 2.7) | 53.2, CH | |
| 22a | 2.11, m | 25.2, CH2 | 1.95, dqd (−11.5, 7.4, 4.0) | 28.5, CH2 | |
| 22b | 1.86, m | 1.48, m | |||
| 23 | 0.96, t (6.9) | 11.6, CH3 | 0.74, t (7.4) | 10.0, CH3 | |
| NH | 7.10, d (7.7) | 7.50, d (9.0) | |||
| N-Me-Phe-thn-ca | 24 | - | 173.7, C | - | 168.9, C |
| 25 | - | 84.0, C | - | 84.0, C | |
| 26a | 3.74, d (−11.5) | 43.1, CH2 | 3.29, d (−11.6) | 41.5, CH2 | |
| 26b | 3.17, d(−11.3) | 3.18, d(−11.7) | |||
| 27 | 1.35, s | 24.3, CH3 | 1.38, s | 23.9, CH3 | |
| 28 | - | 173.9, C | - | 173.9, C | |
| 29 | 5.39, dd (10.7, 6.4) | 58.9, CH | 5.87, dd (12.2, 3.0) | 55.8, CH | |
| 30a | 3.24, m | 36.0, CH2 | 3.55, br | 36.1, CH2 | |
| 30b | 3.16, m | 3.28, m | |||
| 31 | - | 135.5, C | - | 137.7, C | |
| 32/36 | 7.33, m | 129.2, CH | 7.18, m | 129.6, CH | |
| 33/35 | 7.22, m | 128.5, CH | 7.03, br | 129.3, CH | |
| 34 | 7.20, m | 127.6, CH | 7.08, m | 127.3, CH | |
| 37 | 3.21, s | 30.7, CH3 | 3.17, s | 30.2, CH3 | |
| Pro | 38 | - | 172.7, C | - | 171.2, C |
| 39 | 4.84, dd (8.8,5.1) | 57.5, CH | 5.10, br | 58.8, CH | |
| 40a | 2.22, m | 27.5, CH2 | 2.30, m | 31.2, CH2 | |
| 40b | 1.93, m | 2.10, m | |||
| 41a | 1.99, m | 24.9, CH2 | 2.01, m | 21.7, CH2 | |
| 41b | 1.63, m | ||||
| 42a | 3.97, m | 47.8, CH2 | 3.80, m | 46.9, CH2 | |
| 42b | 3.53, m | 3.69, m | |||
| N-Me-Val | 43 | - | 168.6, C | - | 168.5, C |
| 44 | 4.98, d (11.0) | 60.0, CH | 5.01, d (10.8) | 58.1, CH | |
| 45 | 2.32, m | 27.4, CH | 2.35, m | 28.1, CH | |
| 46 | 0.98, d (6.4) | 19.6, CH3 | 0.95, d (6.7) | 19.5, CH3 | |
| 47 | 0.88, d (6.6) | 18.0, CH3 | 0.85, d (6.7) | 18.6, CH3 | |
| 48 | 3.12, s | 30.0, CH3 | 3.20, s | 30.3, CH3 | |
| Pla | 49 | - | 170.2, C | - | 171.4, C |
| 50 | 5.33, dd (9.9, 3.2) | 72.4, CH | 5.33, dd (9.7, 3.8) | 72.4, CH | |
| 51a | 3.09, dd (−14.5, 9.9) | 36.9, CH2 | 3.16, m | 36.9, CH2 | |
| 51b | 3.04, dd (−14.4, 3.2) | 3.01, m | |||
| 52 | - | 134.9, C | - | 136.1, C | |
| 53/57 | 7.22, m | 129.1, CH | 7.12, m | 129.1, CH | |
| 54/56 | 7.24, m | 129.5, CH | 7.31, m | 129.5, CH | |
| 55 | 7.27, m | 127.6, CH | 7.24, m | 127.4, CH | |