Table 3.
1H (500 MHz) and 13C (100 MHz) NMR Spectroscopic Data for Compound 3 in Pyridine-d5a
| residue | position | δC, type | δH (J, Hz) | residue | position | δC, type | δH (J, Hz) |
|---|---|---|---|---|---|---|---|
| MeHA | 1 | 166.9, C | - | Leu1 | 1 | 176.8, C | - |
| 2 | 121.4, CH | 6.38, d (15.2) | 2 | 56.6, CH | 4.50, m | ||
| 3 | 152.2, CH | 7.14, dd (15.2, 7.8) | 3 | 41.1, CH2 | 2.12, 2.42, m | ||
| 4 | 39.05, CH | 2.33, m | 4 | 25.51, CH | 2.31, m | ||
| 5 | 29.8, CH2 | 1.42, 1.61, m | 5 | 22.5, CH3 | 0.97b | ||
| 6 | 12.6, CH3 | 1.00b | 6 | 23.5, CH3 | 1.11, d (6.4) | ||
| 7 | 19.8, CH3 | 1.08, d (6.7) | CONH | - | 8.13, br d (4.9) | ||
| MePro | 1 | 176.2, C | - | Leu2 | 1 | 175.7, C | - |
| 2 | 64.7, CH | 4.52, m | 2 | 57.2, CH | 4.44, m | ||
| 3 | 39.9, CH2 | 1.74, 2.42, m | 3 | 40.7, CH2 | 2.23, m | ||
| 4 | 34.3, CH | 2.12, m | 4 | 25.46, CH | 2.11, m | ||
| 5 | 55.2, CH2 | 3.68, 3.88, m | 5 | 23.1, CH3 | 1.00b | ||
| 6 | 17.2, CH3 | 0.93b | 6 | 23.25, CH3 | 0.95b | ||
| AHMD | 1 | 177.6. C | - | CONH | - | 8.76c | |
| 2 | 56.4, CH | 4.70, m | Aib2 | 1 | 176.6, C | - | |
| 3 | 36.5, CH2 | 1.62, 2.40, m | 2 | 57.0, C | - | ||
| 4 | 27.6, CH | 2.30, m | 3 | 23.7, CH3 | 1.75, s | ||
| 5 | 46.5, CH2 | 1.40, 1.60, m | 4 | 27.9, CH3 | 1.85, s | ||
| 6 | 68.1, CH | 3.85, m | CONH | - | 8.70, s | ||
| 7 | 39.07, CH2 | 1.54, 1.61, m | Aib3 | 1 | 178.0, C | - | |
| 8 | 29.0, CH2 | 1.50, 1.69, m | 2 | 57.5, C | - | ||
| 9 | 23.8, CH2 | 1.35, m | 3 | 23.29, CH3 | 1.68, s | ||
| 10 | 14.9, CH3 | 0.91b | 4 | 28.3, CH3 | 1.86, s | ||
| 11 | 20.7, CH3 | 1.05, d (6.6) | CONH | - | 8.16, s | ||
| CONH | - | 10.09, br d (6.5) | β-Ala | 1 | 174.8, C | - | |
| β-HyLeu | 1 | 174.0, C | - | 2 | 38.5, CH2 | 2.39, 3.27, m | |
| 2 | 63.8, CH | 4.59, dd (9.0, 4.6) | 3 | 38.3, CH2 | 3.33, 4.26, m | ||
| 3 | 74.1, CH | 4.51, m | CONH | - | 8.63, br dd (9.1, 4.2) | ||
| 4 | 30.9, CH | 2.24, m | MPD | 1 | 56.2, CH2 | 3.27, 3.73, m | |
| 5 | 15.8, CH3 | 1.41b | 2 | 43.2, CH | 4.68, m | ||
| 6 | 21.7, CH3 | 1.42b | 3 | 18.3, CH3 | 1.26b | ||
| CONH | - | 9.47, br d (4.6) | 4 | 34.8, CH3 | 2.99, s | ||
| Aib1 | 1 | 177.8, C | - | CONH | - | 7.77, br d (8.0) | |
| 2 | 57.3, C | - | NH-2 | - | n.d.d | ||
| 3 | 23.6, CH3 | 1.79, s | |||||
| 4 | 27.3, CH3 | 1.94, s | |||||
| CONH | - | 9.19, s |
a
Abbreviations: MeHA, 4-methyl-2-hexenoic acid; MePro, 4-methylproline; AHMD, 2-amino-6-hydroxy-4-methyldecanoic acid; β-HyLeu, β-hydroxyleucine; Aib, 2-aminobutyric acid; Leu, leucine; β-Ala, β-alanine; MPD, N1-methylpropane-1,2-diamine.
b
Multiplicity was not determined due to overlapping signal.
c
Overlapped with solvent signal; chemical shift was extracted from the COSY and HMBC correlation data.
d
Not detected.