Table 2.
1H and 13C data (CDCl3) of SphA degradation metabolite (SphA-Met 10). Chemical shifts reported in δ-values (ppm) from CDCl3 reference
| Atom (C) | 13Ca δ (ppm) | 1Ha δ (ppm) | HMBC 1H–13 (ppm) |
|---|---|---|---|
| 1 | 24.0 | 2.03 [1.98–2.05], m, 1H | 1.56 (3′) |
| 1’ | 2.12 [2.09–2.18], m, 1H | ||
| 2 | 19.3 | 1.67 [1.62–1.70], m, 1H | 2.12 (1′) |
| 2’ | 1.75 [1.72–1.77], m, 1H | ||
| 3 | 38.8 | 1.46 [1.42–1.50], m, 1H | 1.25 (18) |
| 3’ | 1.56 [1.53–1.60], m, 1H | ||
| 4 | 30.8 | — | 1.20 (19), 1.25 (18), 1.56 (3′) |
| 5 | 133.0 | — | 2.12 (1′), 1.20 (19), 1.25 (18), 1.56 (3′) |
| 6 | 172.0 | — | 1.20 (19), 1.25 (18), 2.03 (1), 1.56 (3′) |
| 7b | 169.5 | — | 7.20 (14) |
| 8b | 125.6 | — | 7.20 (14), 1.82 (11), 1.94 (11′) |
| 9 | 82.0 | — | 1.65 (12), 1.82 (11), 1.94 (11′/12′), 2.03 (1), 2.12 (1′) |
| 10 | 164.3 | — | 2.12 (1′), 1.67 (2), 1.94 (11′) |
| 11 | 31.7 | 1.82 [1.78–1.85], m, 1H | 1.65 (12), 1.94 (12′) |
| 11′ | 1.94 [1.89–1.98], m, 1H | ||
| 12 | 31.0 | 1.65 [1.62–1.70], m, 1H | 1.20 (17), 5.80 (15) |
| 12′ | 1.94 [1.89–1.98], m, 1H | ||
| 13 | 39.5 | — | 1.20 (17), 1.65 (12), 1.82 (11), 1.94 (11′/12′), 5.06 (16), 5.11 (16′), 5.80 (15) |
| 14 | 156.0 | 7.20, br s, 1H | 1.20 (17), 1.65 (12), 5.80 (15) |
| 15 | 143.8 | 5.80, dd, 1H, J = 17.4, 10.5 Hz | 1.20 (17), 1.65 (12), 1.94 (12′), 5.06 (16) |
| 16 | 114.3 | 5.06, d, 1H, J = 17.4 Hz | |
| 16′ | 5.11, d, 1H, J = 10.5 Hz | ||
| 17 | 25.1 | 1.20, S, 3H | 1.65 (12), 1.94 (12′), 5.80 (15) |
| 18c | 27.0 | 1.25, S, 3H | 1.20 (19), 1.46 (3) |
| 19c | 25.9 | 1.20, S, 3H | 1.25 (18) |
a
1H and 13C signals assigned accordingly by implementing 2D 1H, 1H (COSY), 2D 13C, 1H (HSQC, HMBC) and APT NMR spectroscopy.
b
13C NMR spectroscopy signal not visible in original 13C NMR spectra, but identified from additional HMBC correlation cross-peaks. Assignments in red obtained from the additional HMBC correlation information (Fig. S22†).
c
13C and 1H NMR spectroscopic signals of 18 and 19 are interchangeable.