TABLE 2.
NMR spectral data a of pestahivin (1).
| Amino acid residue | Position | 13C | 1H, mult. (J = Hz) |
|---|---|---|---|
| N-Me-Ala (MALA-1) | N-Me | 36.7, CH3 | 3.19, s |
| α | 58.3, CH | 3.98, q (6.8) | |
| β | 13.4, CH3 | 1.36, d (6.7) | |
| CO | 170.0, C | ||
| (R)-2-hydroxy-4-cyanobutyric acid (DGCN-2) | 1 | 73.6, CH | 4.88, dd (3.5, 10.4) |
| 2 | 26.4, CH2 | 1.71, m; 2.00, m | |
| 3 | 13.1, CH2 | 2.42, m; 2.46, m | |
| 4 | 120.7, C | ||
| CO | 167.3, C | ||
| (4R)-5-propyl-L-leucine (PrLEU-3) | NH | 7.85, d (9.6) | |
| 1 | 46.5, CH | 4.68, q (7.7) | |
| 2 | 39.4, CH2 | 1.50, m; 1.50, m | |
| 3 | 28.1, CH | 1.27, m | |
| 3-Me | 20.0, CH3 | 0.80, d (6.4) | |
| 4 | 36.3, CH2 | 1.07, m; 1.18, m | |
| 5 | 28.5, CH2 | 1.17, m; 1.27, m | |
| 6 | 22.4, CH2 | 1.24, m; 1.24, m | |
| 7 | 13.9, CH3 | 0.86, t (6.9) | |
| CO | 169.8, C | ||
| N-Me-Leu (MLEU-4) | N-Me | 27.9, CH3 | 2.40, s |
| α | 57.3, CH | 4.09, m | |
| β | 35.9, CH2 | 1.57, m; 1.64, m | |
| γ | 24.4, CH | 1.35, m | |
| δ | 21.6, CH3 | 0.94, d (6.7) | |
| δ’ | 23.3, CH3 | 0.92, d (6.9) | |
| CO | 171.5, C | ||
| Leu (LEU-5) | N-H | 8.33, d (6.4) | |
| α | 47.4, CH | 4.09, m | |
| β | 36.5, CH2 | −0.70, m; 1.36, m | |
| γ | 22.8, CH | 1.23, m | |
| δ | 18.1, CH3 | −0.20, d (6.6) | |
| δ' | 22.5, CH3 | 0.40, d (6.4) | |
| CO | 172.6, C | ||
| N’-methoxy-N-methyl-L-tryptophan (MTO-6) | N-Me | 28.6, CH3 | 2.78, s |
| 1 | 60.4, CH | 4.83, dd (4.1, 10.7) | |
| 2 | 23.1, CH2 | 3.05, m; 3.10, m | |
| 3 | 106.2, C | ||
| 4 | 122.9, CH | 7.36, s | |
| 5-OMe | 65.8, CH3 | 4.01, s | |
| 6 | 131.7, C | ||
| 7 | 123.4, C | ||
| 8 | 118.6, CH | 7.63, d (7.7) | |
| 9 | 119.7, CH | 7.07, t (7.0) | |
| 10 | 122.3, CH | 7.20, t (7.7) | |
| 11 | 108.3, CH | 7.43, d (8.4) | |
| CO | 167.9, C | ||
| (4R)-5-propyl-L-leucine (PrLEU-7) | N-H | 8.60, d (9.9) | |
| 1 | 46.1, CH | 4.91, m | |
| 2 | 38.4, CH2 | 1.26, m; 1.51, m | |
| 3 | 28.2, CH | 0.87, m | |
| 3-Me | 18.7, CH3 | 0.87, d (6.1) | |
| 4 | 36.5, CH2 | 1.05, m; 1.30, m | |
| 5 | 28.7, CH2 | 1.16, m; 1.28, m | |
| 6 | 22.3, CH2 | 1.24, m; 1.24, m | |
| 7 | 14.0, CH3 | 0.86, t (6.9) | |
| CO | 170.4, C |
a1H (400 MHz) and
13C (100 MHz) in DMSO-d 6 . Assignments based on COSY, HSQC and HMBC and comparison with literature. Chemical shifts (δ) in ppm. s, singlet; d, doublet; t, triplet, m, multiplet, dd, doublet of doublet; q, quartet.