Table 1.
1H (500 MHz) and 13C (100 MHz) NMR Spectroscopic Data for Compound 1 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 | 6.39, d (15.2) | 2 | 56.6, CH | 4.51, m | ||
| 3 | 152.0, CH | 7.15, dd (15.2, 7.8) | 3 | 41.1, CH2 | 2.12, 2.44, m | ||
| 4 | 39.1, CH | 2.36, m | 4 | 25.5, CH | 2.33, m | ||
| 5 | 29.8, CH2 | 1.44, 1.64, m | 5 | 22.5, CH3 | 0.99b | ||
| 6 | 12.6, CH3 | 1.03b | 6 | 23.5, CH3 | 1.12, d (7.3) | ||
| 7 | 19.8, CH3 | 1.10, d (7.2) | CONH | - | 8.10, br d (5.0) | ||
| MePro | 1 | 176.3, C | - | Leu2 | 1 | 175.7, C | - |
| 2 | 64.6, CH | 4.55, m | 2 | 57.3, CH | 4.44, m | ||
| 3 | 39.9, CH2 | 1.76, 2.44, m | 3 | 40.7, CH2 | 2.16, 2.26, m | ||
| 4 | 34.3, CH | 2.13, m | 4 | 25.4, CH | 2.12, m | ||
| 5 | 55.2, CH2 | 3.71, 3.89, m | 5 | 23.1, CH3 | 0.95, d (6.5) | ||
| 6 | 17.1, CH3 | 0.97b | 6 | 23.2, CH3 | 1.00b | ||
| AMOD | 1 | 177.6. C | - | CONH | - | 8.81, br d (4.7) | |
| 2 | 56.3, CH | 4.64, m | Aib2 | 1 | 176.6, C | - | |
| 3 | 37.5, CH2 | 1.69, 2.20, m | 2 | 57.0, C | - | ||
| 4 | 30.2, CH | 1.94, m | 3 | 23.6, CH3 | 1.76, s | ||
| 5 | 37.5, CH2 | 1.18, 1.35, m | 4 | 28.0, CH3 | 1.86, s | ||
| 6 | 21.79, CH2 | 1.56, 1.66, m | CONH | - | 8.76c | ||
| 7 | 43.1, CH2 | 2.33, m | Aib3 | 1 | 178.0, C | - | |
| 8 | 211.0, C | - | 2 | 57.5, C | - | ||
| 9 | 36.1, CH2 | 2.34, m | 3 | 23.3, CH3 | 1.68, s | ||
| 10 | 8.5, CH3 | 1.02b | 4 | 28.4, CH3 | 1.87, s | ||
| 11 | 18.9, CH3 | 0.91, d (6.6) | CONH | - | 8.17, s | ||
| CONH | - | 10.25, br d (6.8) | β-Ala | 1 | 174.8, C | - | |
| β-HyLeu | 1 | 174.0, C | - | 2 | 38.5, CH2 | 2.40, 3.29, m | |
| 2 | 64.0, CH | 4.55, m | 3 | 38.3, CH2 | 3.34, 4.27, m | ||
| 3 | 73.9, CH | 4.55, m | CONH | - | 8.66, br dd (9.0, 4.3) | ||
| 4 | 30.9, CH | 2.25, m | MPD | 1 | 56.2, CH2 | 3.27, 3.77, m | |
| 5 | 15.7, CH3 | 1.43b | 2 | 43.2, CH | 4.68, m | ||
| 6 | 21.75, CH3 | 1.44b | 3 | 18.3, CH3 | 1.27, d (6.7) | ||
| CONH | - | 9.65, br s | 4 | 34.8, CH3 | 3.00, s | ||
| Aib1 | 1 | 177.7, C | - | CONH | - | 7.75, br d (8.6) | |
| 2 | 57.2, C | - | NH-2 | - | n.d.d | ||
| 3 | 23.6, CH3 | 1.79, s | |||||
| 4 | 27.4, CH3 | 1.95, s | |||||
| CONH | - | 9.26, s |
a
Abbreviations: MeHA, 4-methyl-2-hexenoic acid; MePro, 4-methylproline; AMOD, 2-amino-4-methyl-8-oxodecanoic 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 HMBC correlation data.
d
Not detected.