TABLE 3.
NMR spectral data of pestahivins B (2) and C (3).
| Amino acid residue | Position | 2 a | 3 b | ||
|---|---|---|---|---|---|
| 13C | 1H, mult. (J = Hz) | 13C | 1H, mult. (J = Hz) | ||
| N-Me-Ala (MALA-1) | N-Me | 36.6, CH3 | 3.18, s | 36.7, CH3 | 3.19, s |
| α | 58.3, CH | 3.95, q (6.8) | 58.3, CH | 3.97, q (6.8) | |
| β | 13.3, CH3 | 1.37, d (6.7) | 13.4, CH3 | 1.37, d (6.8) | |
| CO | 169.9, C | 170.0, C | |||
| (R)-2-hydroxy-4-cyanobutyric acid (DGCN-2) | 1 | 73.5, CH | 4.90, m | 73.6, CH | 4.88, dd (2.8, 10.9) |
| 2 | 26.3, CH2 | 1.71, m; 2.00, m | 26.4, CH2 | 1.70, m; 1.99, m | |
| 3 | 13.1, CH2 | 2.42, m; 2.46, m | 13.2, CH2 | 2.45, m; 2.45, m | |
| 4 | 120.6, CN | 120.7, CN | |||
| CO | 167.2, C | 167.3, C | |||
| (4R)-5-propyl-L-leucine (PrLEU-3) | N-H | 7.84, d (9.6) | 7.84, d (9.6) | ||
| 1 | 46.4, CH | 4.68, q (7.0) | 46.5, CH | 4.67, q (6.9) | |
| 2 | 39.3, CH2 | 1.49, m; 1.49, m | 39.4, CH2 | 1.50, m; 1.50, m | |
| 3 | 28.1, CH | 1.28, m | 28.1, CH | 1.28, m | |
| 3-Me | 19.9, C | 0.80, d (6.4) | 20.0, C | 0.80, d (6.3) | |
| 4 | 36.3, CH2 | 1.09, m; 1.19, m | 36.3, CH2 | 1.09, m; 1.18, m | |
| 5 | 28.5, CH2 | 1.17, m; 1.27, m | 28.6, CH2 | 1.17, m; 1.27, m | |
| 6 | 22.3, CH2 | 1.25, m; 1.25, m | 22.4, CH2 | 1.24, m; 1.24, m | |
| 7 | 13.9, CH3 | 0.85, t (6.8) | 14.0, CH3 | 0.86, t (6.9) | |
| CO | 169.8, C | 169.9, C | |||
| N-Me-Leu (MLEU-4) | N-Me | 27.8, CH3 | 2.40, s | 27.9, CH3 | 2.39, s |
| α | 57.3, CH | 4.10, m | 57.3, CH | 4.08, m | |
| β | 35.9, CH2 | 1.57, m; 1.64, m | 35.9, CH2 | 1.58, m; 1.64, m | |
| γ | 24.3, CH | 1.36, m | 24.4, CH | 1.37, m | |
| δ | 21.5, CH3 | 0.94, d (6.7) | 21.6, CH3 | 0.94, d (7.1) | |
| δ’ | 23.3, CH3 | 0.92, d (6.9) | 23.3, CH3 | 0.92, d (7.5) | |
| CO | 171.5, C | 171.5, C | |||
| Leu (LEU-5) | N-H | 8.35, d (6.3) | 8.33, d (6.2) | ||
| α | 47.3, CH | 4.10, m | 47.4, CH | 4.09, m | |
| β | 36.5, CH2 | −0.70, m; 1.40, m | 36.5, CH2 | −0.71, m; 1.39, m | |
| γ | 22.7, CH | 1.23, m | 22.8, CH | 1.22, m | |
| δ | 18.0, CH3 | −0.19, d (6.6) | 18.1, CH3 | −0.19, d (6.6) | |
| δ' | 22.5, CH3 | 0.40, d (6.4) | 22.5, CH3 | 0.39, d (6.4) | |
| CO | 172.6, C | 172.7, C | |||
| N’-methoxy-N-methyl-L-tryptophan (MTO-6) | N-Me | 28.4, CH3 | 2.79, s | 28.6, CH3 | 2.79, s |
| 1 | 60.3, CH | 4.84, m | 60.3, CH | 4.83, dd (3.4, 10.6) | |
| 2 | 23.0, CH2 | 3.04, m; 3.13, m | 23.1, CH2 | 3.03, m; 3.11, m | |
| 3 | 106.1, C | 106.2, C | |||
| 4 | 122.8, CH | 7.34, s | 122.9, CH | 7.36, s | |
| 5-OMe | 65.7, CH3 | 4.01, s | 65.8, CH3 | 4.01, s | |
| 6 | 131.7, C | 131.7, C | |||
| 7 | 123.3, C | 123.4, C | |||
| 8 | 118.5, CH | 7.62, d (8.0) | 118.6, CH | 7.62, d (8.0) | |
| 9 | 119.6, CH | 7.07, t (7.6) | 119.7, CH | 7.07, t (7.8) | |
| 10 | 122.3, CH | 7.19, t (7.5) | 122.4, CH | 7.20, t (7.3) | |
| 11 | 108.3, CH | 7.42, d (8.2) | 108.4, CH | 7.43, d (8.1) | |
| CO | 167.7, C | 167.9, C | |||
| Leu (LEU-7 in 2) | N-H | 8.62, d (10.0) | |||
| α | 46.2, CH | 4.88, m | |||
| β | 39.3, CH2 | 1.31, m; 1.44, m | |||
| γ | 23.6, CH | 1.31, m | |||
| δ | 21.8, CH3 | 0.89, d (6.0) | |||
| δ' | 23.0, CH3 | 0.87, d (6.5) | |||
| CO | 170.3, C | ||||
| (4R)-5-methyl-L-leucine (MeLEU-7 in 3) | N-H | 8.62, d (10.0) | |||
| 1 | 46.2, CH | 4.90, q (5.1) | |||
| 2 | 37.9, CH2 | 1.29, m; 1.50, m | |||
| 3 | 29.9, CH | 1.11, m | |||
| 3-Me | 18.3, CH3 | 0.87, d (5.9) | |||
| 4 | 29.4, CH2 | 1.10, m; 1.39, m | |||
| 5 | 11.2, CH3 | 0.82, t (6.8) | |||
| CO | 170.5, C | ||||
a1H (400 MHz) and 13C (100 MHz) in DMSO-d 6:chloroform-d (10:1).
b1H (400 MHz) and 13C (100 MHz) in DMSO-d 6. Assignments based on COSY, HSQC and HMBC. Chemical shifts (δ) in ppm. s, singlet; d, doublet; t, triplet, m, multiplet, dd, doublet of doublet; q, quartet.