Table 3.
NMR (B0 = 11.74 T) data on MTM SA-Trpa.
| Position | δH (J in Hz) | δCb, multiplicity | HMBC |
|---|---|---|---|
| 1 | (203.5, C)c | ||
| 2 | 4.43, d (11.5) | 77.4, CH | 44.6, 102.1 |
| 3 | 2.29, d (13.0) | 44.6, CH | |
| 4 | 1.73–1.98 (m, 5 H) 2.32–2.42 (m, 1 H) | 27.2, CH2 | 77.4, 80.8, 117.9, 135.9 |
| 4a | 135.9, C | ||
| 5 | 6.56, s | 101.7, CH | 108.2, 111.3, 117.9, 159.6 |
| 6 | 159.6, C | ||
| 7 | 111.3, C | ||
| 7-CH3 | 2.14, s | 8.7, CH3 | 111.3, 156.4, 159.6 |
| 8 | 156.4, C | ||
| 8a | 108.2, C | ||
| 9 | (164.5, C)d | ||
| 9a | 102.1, C | ||
| 10 | 5.93, s | 117.9, CH | 27.2, 101.7, 108.2, 139.1 |
| 10a | 139.1, C | ||
| 1′ | 4.06, s | 80.8, CH | 27.2, 44.6, 59.9, 77.4, 173.9 |
| 1′-OCH3 | 3.47, s | 59.9, CH3 | 80.8 |
| 2′ | 173.9, C | ||
| 4′ | 4.95–5.02 (m, complex) | 53.1, CH | 173.2, 173.9 |
| 5′ | 173.2, C | ||
| 5′-OCH3 | 3.81, s | 52.8, CH3 | 173.2 |
| 2″ | 7.21, s (overlap) | 124.1, CH | 110.9, 112.3, 119.3, 128.5, 137.8 |
| 3″ | 110.9, C | ||
| 3″a | 128.5, C | ||
| 4″ | 7.66, d (7.5) | 119.3, CH | 110.9, 112.3, 122.7, 128.5, 137.8 |
| 5″ | 7.21, t (7.5) (overlap) | 122.7, CH | 110.9, 112.3, 119.3, 128.5, 137.8 |
| 6″ | 7.06, t (7.5) | 119.9, CH | 110.9, 112.3, 124.1, 128.5, 137.8 |
| 7″ | 7.43, d (8.0) | 112.3, CH | 119.9, 124.1, 128.5 |
| 7″a | 137.8, C | ||
| 8″ | 3.37–3.43 (m, 2 H) 3.50, dd (4.3, 15.3) | 28.0, CH2 | 53.1, 110.9, 124.1, 128.5 53.1, 110.9, 124.1, 128.5 |
| 1A | 5.32, d (9.0) | 97.7, CH | |
| 2A | 1.73–1.98 (m, 5 H) 2.48, dd (4.0, 10.5) | 37.9, CH2 | 97.7 76.0, 80.3 |
| 3A | 3.65–3.78 (m, 4 H) | 80.3, CH | |
| 4A | 3.04, t (9.0) | 76.0, CH | 18.2, 73.2, 80.3 |
| 5A | 3.32–3.34 (m, 1 H) | 73.2, CH | |
| 6A | 1.44, d (6.0) | 18.2, CH3 | 73.2, 76.0 |
| 1B | 4.65, dd (1.5, 9.5) | 99.7, CH | 80.3 |
| 2B | 1.50–1.66 (m, 3 H) 2.22 (m, 1 H) | 40.4, CH2 | 71.4, 99.7 71.4, 77.8, 99.7 |
| 3B | 3.65–3.78 (m, 4 H) | 71.4, CH | 77.8 |
| 4B | 2.98, t (9.0) | 77.8, CH | 17.6, 71.4, 73.2 |
| 5B | 3.65–3.78 (m, 4 H) | 73.2, CH | |
| 6B | 1.31–1.37 (m, 6 H) | 17.6, CH3 | 73.2, 77.8 |
| 1C | 5.04, d (9.5) | 101.8, CH | |
| 2C | 1.50–1.66 (m, 3 H) 2.56, dd (4.0, 11.0) | 37.9, CH2 | 80.5, 101.8 76.0, 80.5, 101.8 |
| 3C | 3.83–3.93 (m, 2 H) | 80.5, CH | 76.0 |
| 4C | 3.14, t (8.8) | 76.0, CH | 18.2, 73.4, 80.5 |
| 5C | 3.37–3.43 (m, 2 H) | 73.4, CH | |
| 6C | 1.31–1.37 (m, 6 H) | 18.2, CH3 | 73.2, 76.0 |
| 1D | 4.78, dd (1.0, 9.5) | 100.0, CH | 80.5 |
| 2D | 1.73–1.98 (m, 5 H) 1.73–1.98 (m, 5 H) | 33.0, CH2 | 77.0, 100.0 70.2, 77.0, 100.0 |
| 3D | 3.83–3.93 (m, 2 H) | 77.0, CH | 100.0 |
| 4D | 3.65–3.78 (m, 4 H) | 70.2, CH | 77.0 |
| 5D | 3.54–3.64 (m, 3 H) | 71.4, CH | 16.8, 70.2 |
| 6D | 1.29, d (6.5) | 16.8, CH3 | 70.2, 71.4 |
| 1E | 4.95–5.02 (m, 2 H) | 98.8, CH | 27.5, 44.8, 77.0 |
| 2E | 1.50–1.66 (m, 3 H) 1.73–1.98 (m, 5 H) | 44.8, CH2 | 71.4, 98.8 71.4, 77.4, 98.8 |
| 3E | 70.0, C | ||
| 3E-CH3 | 1.24, s | 27.5, CH3 | 44.8, 71.4, 77.4, 98.8 |
| 4E | 2.92, d (9.5) | 77.8, CH | 18.2, 71.4 |
| 5E | 3.54–3.64 (m, 3 H) | 71.4, CH | 70.0, 98.8 |
| 6E | 1.26, d (6.5) | 18.2, CH3 | 77.8, 71.4 |
a
The solvent used for NMR experiments was methanol-d4.
b
13C NMR data was inferred from gHSQC and gHMBC spectra.
c
The numbers in the parentheses are based on previously published mithramycin data [19].