1H NMR and 13C NMR chemical shift assignment (ppm) of FYX-051 and its conjugates
FYX-051 | Glucuronide A | Glucuronide B | Glucoside A | Glucoside B | |
|---|---|---|---|---|---|
| Proton | |||||
| H1 | 15.34 (1H, br) | ||||
| H8 | 8.47 (1H, dd, J = 1.6, 1.1) | 8.56 (1H, s) | 8.36 (1H, s) | 8.55 (1H, d, J = 0.4) | 8.42 (1H, d, J = 0.3) |
| H10 | 8.25 (1H, dd, J = 5.0, 1.9) | 8.33 (1H, dd, J = 5.1, 1.6) | 8.11 (1H, d, J = 4.4) | 8.32 (1H, dd, J = 5.2, 1.6) | 8.16 (1H, dd, J = 5.2, 1.6) |
| H11 | 8.88 (1H, dd, J = 5.3, 1.1) | 8.91 (1H, d, J = 5.2) | 9.01 (1H, d, J = 5.0) | 8.92 (1H; d, J = 5.2) | 9.00 (1H, d, J = 5.2) |
| H14/H18 | 8.76 (2H, dd, J = 4.6, 1.9) | 8.85 (2H, d, J = 5.8) | 8.79 (2H, br) | 8.86 (2H, dd, J = 4.4, 1.6) | 8.75 (2H, d, J = 4.5, 1.6) |
| H15/H17 | 7.96 (2H, dd, J = 4.6, 1.9) | 7.83 (2H, d, J = 5.8) | 8.05 (2H, br) | 7.84 (2H, dd, J = 4.4, 1.6) | 8.01 (2H, d, J = 4.6, 1.6) |
| H1′ | 5.38 (1H, d, J = 8.3) | 5.66 (1H, d, J = 8.3) | 5.35 (1H, d, J = 8.9) | 5.46 (1H, d, J = 8.9) | |
| H2′ | 4.03 (1H, m) | 3.97 (1H, m) | 4.09 (1H, m) | 4.02 (1H, t, J = 8.9) | |
| H3′ | 3.41 (1H, m) | 3.47 (1H, m) | 3.39 (1H, m) | 3.42 (1H, t, J = 8.9) | |
| H4′ | 3.36 (1H, m) | 3.51 (1H, m) | 3.24 (1H, m) | 3.24 (1H, t, J = 9.1) | |
| H5′ | 3.68 (1H, br, J = 7.3) | 4.14 (1H, d, J = 7.9) | 3.52 (1H, m) | 3.59 (1H, m) | |
| H6′ | 3.80 (1H, m) | 3.78 (1H, d, J = 11.7) | |||
| 3.49 (1H, m) | 3.51 (1H, m) | ||||
| 2′OH | 5.42 (1H, d, J = 6.0) | 5.56 (1H, br) | |||
| 3′OH | 5.37 (1H, br) | 5.27 (1H, d, J = 5.2) | 5.38 (1H, br) | ||
| 4′OH | 5.17 (1H, d, J = 5.4) | 5.26 (1H, br) | |||
| 6′OH | 4.79 (1H, t, J = 6.0) | 4.81 (1H, br) | |||
| Carbon | |||||
| C3 | 156.5 | 157.1 | 153.6 | 157.1 | 153.6 |
| C5 | 155.9 | 155.4 | 159.1 | 155.6 | 155.8 |
| C7 | 138.1 or 133.5 | 139.0 or 133.6 | 135.6 or 133.6 | 138.9 or 133.6 | 135.7 or 133.7 |
| C8 | 125.0 | 125.2 | 128.3 | 125.2 | 128.1 |
| C9 | 138.1 or 133.5 | 139.0 or 133.6 | 135.6 or 133.6 | 138.9 or 133.6 | 135.7 or 133.7 |
| C10 | 123.6 | 123.7 | 127.2 | 123.8 | 127.0 |
| C11 | 152.2 | 152.2 | 152.1 | 152.2 | 152.1 |
| C12 | 117.2 | 117.1 | 117.0 | 117.2 | 117.0 |
| C14/C18 | 150.6 | 150.5 | 150.5 | 150.6 | 150.5 |
| C15/C17 | 120.1 | 123.1 | 120.6 | 123.0 | 120.2 |
| C16 | 134.7 | 133.9 | 136.8 | 133.8 | 137.0 |
| C1′ | 86.0 | 85.6 | 86.0 | 85.8 | |
| C2′ | 71.3 | 71.5 | 71.3 | 71.3 | |
| C3′ | 76.6 | 75.8 | 76.7 | 76.6 | |
| C4′ | 71.7 | 71.1 | 69.7 | 69.7 | |
| C5′ | 75.8 | 77.0 | 79.8 | 79.6 | |
| C6′ |
| 171.5 | 169.6 | 60.8 | 60.8 |
s, singlet; d, doublet; dd, doublet of doublet; t, triplet; m, multiplet; br, broad; J, coupling constant (Hz).