1H NMR and HMBC data for M (minocycline) and minocycline-NAC adduct M5
NMR Proton/Carbon Numbers | M (Minocycline) | M5 | ||||
|---|---|---|---|---|---|---|
| δH ppm (Multiplicity†) | δC ppm | δH ppm (Multiplicity†) | δC ppm | |||
| 1 | — | 196.23 | — | N.S. | ||
| 2 | — | 97.71 | — | N.S. | ||
| 3 | — | 188.69 | — | 187.46 | ||
| 4 | 4.05 (d, 1H, J = 1.5Hz) | 70.94 | 4.15 (bs, 1H) | 74.03 | ||
| 4a | 2.90-2.97 (m, 1H) | 35.92 | 2.88-2.93 (m, 1H) | 40.00 | ||
| 5 | 1.63 (dt, 1H, J = 11.5, 14 Hz) | 35.08 | 1.80-1.94 (m, 2H) | 30.72 | ||
| 2.16-2.23 (m, 2H) | ||||||
| 5a | 2.90-2.97 (m, 2H) | 33.86 | 2.74-2.77 (m, 1H) | 41.01 | ||
| 6 | 2.16-2.23 (m, 2H) | 31.12 | 3.22-3.26 (m, 2H) | 28.20 | ||
| 3.42 (dd, 1H, J = 4.5, 15.5 Hz) | ||||||
| 6a | — | 139.38 | — | 135.60 | ||
| 7 | — | 144.96 | — | 145.12 | ||
| 8 | 7.43 (d, 1H, J = 9 Hz) | 129.70 | 7.42 (d, 1H, J = 9 Hz) | 130.70 | ||
| 9 | 6.90 (dd, 1H, J = 0.5, 9 Hz) | 117.00 | 6.75 (d, 1H, J = 9 Hz) | 116.90 | ||
| 10 | — | 161.05 | — | 161.04 | ||
| 10a | — | 118.63 | — | 114.82 | ||
| 11 | — | 196.15 | — | N.S. | ||
| 11a | — | 110.65 | — | 68.98 | ||
| 12 | — | 173.56 | — | N.S. | ||
| 12a | — | 75.75 | — | 82.19 | ||
| 13 | 3.00 (s, 6H) | 42.47 | 2.66 (s, 6H) | 43.73 | ||
| 14 | 3.00 (s, 6H) | 42.47 | 2.66 (s, 6H) | 43.73 | ||
| 15 | 2.63 (s, 6H) | 45.31 | 2.58 (s, 6H) | 44.90 | ||
| 16 | 2.63 (s, 6H) | 45.31 | 2.58 (s, 6H) | 44.90 | ||
| 17 | — | — | — | N.S. | ||
| 18 | — | — | 2.79 (dd, 1H, J = 9, 13 Hz) | 34.21 | ||
| 3.50 (dd, 1H, J = 4, 13 Hz) | ||||||
| 19 | — | — | 4.51 (dd, 1H, J = 4, 9 Hz) | 55.39 | ||
| 20 | — | — | — | 172.70 | ||
| 21 | — | — | 1.83 (s, 3H) | 22.60 | ||
| 22 | — | — | — | 176.19 | ||
Multiplicity: b, broad; s, singlet; d, doublet; q, quartet; dt, double triplet; dd, double doublet; m, multiplet; —, peaks absent in HMBC spectra. N.S., no peak was observed, presumably because these are quaternary carbons.
↵† NMR acquired in CD3OD.