Position | δH multiplicity (J in Hz) | ||||||
---|---|---|---|---|---|---|---|
Vincristinea,b | M2b | M2c | M3b | ||||
5 | 7.46 d (8) | 7.52 d (8) | 7.50 d (8) | 7.51 d (8) | |||
6 | 7.02 t (8) | 7.01 t (8) | 6.97 t (8) | 7.04 t (8) | |||
7 | 7.09 t (8) | 7.06 t (8) | 7.03 t (8) | 7.15 t (8) | |||
8 | 7.26 d (8) | 7.19 overlapped | 7.30 d (8) | 7.39 d (8) | |||
10a | 4.18 dd (15.5, 10) | 3.47 overlapped | 3.29 overlapped | 3.10 overlapped | |||
10b | 3.15 dd (15.5, 5.5) | 3.16 overlapped | 3.06 overlapped | 3.01 dd (15, 6) | |||
11a | 3.36 obsc | 3.62 overlapped | 3.48 overlapped | 4.14 dd (12.5, 7) | |||
11b | 3.51 overlapped | 2.94 dt (6, 12) | |||||
13a | 2.92 d (14.5) | 7.35 br s | 7.41 s | ||||
13b | 2.86 d (14.5) | ||||||
15a | 1.55 overlapped | 2.12 overlapped | 2.03 ABd | 2.67 overlapped | |||
15b | 1.45 overlapped | ||||||
16 | 0.87 m | 2.33 m | 2.11 md | 2.13 m | |||
17a | 3.51 d (14) | 3.51 overlapped | 3.23 dd (14,2.5)d | 3.11 dd (12.5, 6.5)d | |||
17b | 2.52 dd (14, 4.5) | 3.04 m | 2.95 overlappedd | 3.05 dd (12.5, 3.3)d | |||
18a | 4.06 dd (15.5, 14) | 3.14 overlapped | 2.97 dd (16, 6.5)d | 2.76 dd (13.5, 6) | |||
18b | 2.37 dd (15.5, 4) | 2.21 overlapped | 2.20 br d (16.5)d | 2.67 overlapped | |||
20a | 1.37 q (7.5) | 2.17 overlapped | 2.10 m | 2.44 q (7.5) | |||
20b | 1.77 m | 1.81 m | |||||
21 | 0.91 t (7.5) | 0.80 t (7) | 0.74 t (7.5) | 0.98 t (7.5) | |||
23 | 3.69 s | 3.59 s | 3.52 br s | ||||
2′ | 4.58 s | 4.64 s | 4.52 s | 4.60 s | |||
5′ | 6.90 s | 6.97 br s | 6.90 s | 6.72 s | |||
8′ | 7.23 s | 7.20 s | 7.30 very br | 7.17 s | |||
10a′ | 2.09 ddd (13, 9, 4) | 2.30 overlapped | 2.23 overlapped | 2.20 obsc | |||
10b′ | 1.78 dt (6.5, 12.5) | 2.06 overlapped | 2.04 overlapped | 2.10 overlapped | |||
11a′ | 3.28 obsc | 3.36 overlapped | 3.28 overlapped | 3.36 dt (7, 10.5)d | |||
11b′ | 2.61 dt (3.5, 11) | 2.74 dt (11, 3.5) | 2.54 overlapped | 2.57 dt (4.5, 11) | |||
13a′ | 3.29 obsc | 3.36 overlapped | 3.31 overlapped | 3.28 obsc | |||
13b′ | 2.85 br d (15.5) | 2.91 br d (16) | 2.74 br d (16) | 2.72 br d (16) | |||
14′ | 5.89 dd (10, 5) | 5.90 dd (10, 5) | 5.83 dd (10, 4.8) | 5.76 dd (10, 4.8) | |||
15′ | 5.41 d (10) | 5.41 d (10) | 5.32 d (10) | 5.14 d (10) | |||
17′ | 3.03 s | 3.10 s | 2.86 s | 2.63 s | |||
18′ | 5.15 s | 5.14 s | 5.01 s | 4.95 s | |||
20a′ | 1.54 overlapped | 1.44 m | 1.40 m | 1.20 dq (15, 7.5) | |||
20b′ | 1.41 overlapped | 1.30 m | 0.78 dq (15, 7.5) | ||||
21′ | 0.79 t (7.5) | 0.45 br t (6) | 0.47 t (7) | 0.07 t (7.5) | |||
22′ | 8.93 s | 9.01 s | e | 8.86 s | |||
23′ | 3.91 s | 3.85 s | 3.76 s | 3.95 s | |||
25′ | 2.00 s | 2.02 s | 1.93 s | 1.91 s | |||
27′ | 3.63 s | 3.63 s | 3.56 s | 3.60 s |
s, singlet; d, doublet; t, triplet; q, quartet; dd, double doublet; dt, double triplet; AB, center of AB spin system; m, multiplet; br, broad.
↵ a The vincristine used was isolated from the CYP3A5 incubation mixture.
↵ b In CD3OD at 25°C.
↵ c In DMSO-d6 at 100°C.
↵ d Assignments either made or confirmed by selective 1D ZQFTOCSY experiment.
↵ e Very broad peak with peak width >1 ppm. This peak was observed at 9.04 ppm (br s) at 25°C.