TABLE 1.
1H and 13C NMR chemical shifts and signal assignments for pseudovitamin B12, factor A, and vitamin B12a
| Assignment | Pseudovitamin B12a
|
Factor Aa
|
Vitamin B12b
|
|||
|---|---|---|---|---|---|---|
| δ(1H) (ppm) | δ(13C)c (ppm) | δ(1H) (ppm) | δ(13C) (ppm) | δ(1H) (ppm) | δ(13C) (ppm) | |
| β-CN | 124.2 | NM | ||||
| C1 | 87.9 | 88.5 | 87.9 | |||
| C1A | 0.33 | 22.2 | 0.34 | 22.8 | 0.34 | 22.2 |
| C2 | 50.4 | 50.9 | 50.1 | |||
| C21 | 2.27 | 45.9 | 2.27 | 46.2 | 2.29 | 45.6 |
| C22 | 179.5 | 180.0 | 178.6 | |||
| C2A | 1.29 | 19.8 | 1.29 | 20.0 | 1.29 | 19.6 |
| C3 | 3.94 | 59.5 | 3.96 | 60.2 | 4.06 | 59.2 |
| C31 | 1.86(Hsi) | 28.5 | 1.85(Hsi) | 29.3 | 1.84 | 28.8 |
| C31 | 1.98(Hre) | 28.5 | 1.95(Hre) | 29.3 | 28.8 | |
| C32 | 2.40 | 38.2 | 2.34(Hre) | 38.7 | 2.39 | 37.8 |
| C32 | 2.40 | 38.2 | 2.42(Hsi) | 38.7 | 2.47 | 37.8 |
| C33 | 182.1 | 182.1 | 180.7 | |||
| C4 | 183.2 | 183.7 | 182.8 | |||
| C5 | 111.7 | 112.4 | 110.3 | |||
| C51 | 2.31 | 18.9 | 2.34 | 19.0 | 2.43 | 18.2 |
| C6 | 167.6 | 167.9 | 168.1 | |||
| C7 | 53.8 | 54.6 | 54.2 | |||
| C71 | 2.08(Hre) | 46.5 | 2.05(Hre) | 47.1 | 2.09 | 45.9 |
| C71 | 2.44(Hsi) | 46.5 | 2.42(Hsi) | 47.1 | 2.48 | 45.9 |
| C72 | 179.4 | 179.5 | 177.9 | |||
| C7A | 1.66 | 22.1 | 1.70 | 22.4 | 1.76 | 21.9 |
| C8 | 3.25 | 59.5 | 3.24 | 59.9 | 3.31 | 58.5 |
| C81 | 0.87(Hre) | 29.1 | 0.95(Hre) | 29.3 | 28.8 | |
| C81 | 1.78(Hsi) | 29.1 | 1.85(Hsi) | 29.3 | 1.91 | 28.8 |
| C82 | 1.22(Hre) | 35.1 | 1.22(Hre) | 34.9 | 0.91 | 34.6 |
| C82 | 1.72(Hsi) | 35.1 | 1.79(Hsi) | 34.9 | 1.74 | 34.6 |
| C83 | 181.9 | 181.6 | 180.0 | |||
| C9 | 176.9 | 177.4 | 176.4 | |||
| C10 | 5.94 | 97.3 | 5.94 | 97.6 | 5.98 | 97.7 |
| C11 | 179.3 | 179.5 | 179.7 | |||
| C12 | 51.0 | 51.6 | 50.9 | |||
| C12A | 1.38 | 22.0 | 1.36 | 22.4 | 1.34 | 22.1 |
| C12B | 1.06 | 34.4 | 1.05 | 34.8 | 1.09 | 34.1 |
| C13 | 3.20 | 57.1 | 3.20 | 57.4 | 3.22 | 56.5 |
| C131 | 1.87 | 31.3 | 1.85 | 31.2 | 1.87 | 30.8 |
| C132 | 2.54 | 37.8 | 2.53 | 38.4 | 2.52 | 37.5 |
| C133 | 182.1 | 182.1 | 181.0 | |||
| C14 | 169.6 | 170.5 | 168.8 | |||
| C15 | 105.9 | 106.4 | 106.9 | |||
| C151 | 2.44 | 18.1 | 2.44 | 18.1 | 2.46 | 18.0 |
| C16 | 181.8 | 182.7 | 181.7 | |||
| C17 | 62.4 | 63.0 | 62.0 | |||
| C171 | 1.68(Hsi) | 36.0 | 1.69(Hsi) | 36.5 | 1.71 | 35.3 |
| C171 | 2.51(Hre) | 36.0 | 2.52(Hre) | 36.5 | 2.40 | 35.3 |
| C172 | 1.92(Hre) | 35.7 | 1.94(Hre) | 35.8 | 2.01 | 34.3 |
| C172 | 2.37(Hsi) | 35.7 | 2.40(Hsi) | 35.8 | 2.55 | 34.3 |
| C173 | 178.3 | 178.9 | 177.5 | |||
| C17B | 1.25 | 19.6 | 1.24 | 20.0 | 1.28 | 18.8 |
| C18 | 2.64 | 42.0 | 2.64 | 42.4 | 2.65 | 41.9 |
| C181 | 2.57 | 34.9 | 2.58 | 35.0 | 2.57 | 35.0 |
| C181 | 2.62 | 34.9 | 2.62 | 35.0 | 2.64 | 35.0 |
| C182 | 179.5 | 180.1 | 178.5 | |||
| C19 | 3.97 | 78.4 | 3.97 | 78.9 | 4.00 | 77.7 |
| C175 | 2.78 | 48.71 | 2.77 | 49.0 | 2.85 | 48.3 |
| C175 | 3.48 | 48.71 | 3.50 | 49.0 | 3.50 | 48.3 |
| C176 | 4.16 | 76.12 | 4.17 | 76.1 | 4.19 | 75.8 |
| C177 | 1.14 | 22.03 | 1.14 | 22.3 | 1.15 | 21.8 |
| C1R | 6.40 | 92.2 | 6.37 | 93.0 | 6.25 | 89.8 |
| C2R | 4.14 | 73.34 | 4.15 | 74.3 | 4.17 | 71.7 |
| C3R | 4.57 | 75.75 | 4.59 | 76.9 | 4.62 | 75.9 |
| C4R | 3.91 | 85.86 | 3.92 | 85.9 | 3.93 | 84.9 |
| C5R | 3.62 | 63.3 | 3.63 | 63.5 | 3.64 | 63.3 |
| C5R | 3.81 | 63.3 | 3.81 | 63.5 | 3.82 | 63.3 |
| O2R | 5.61 | 5.62 | ||||
| C2N | 8.00 | 156.6 | 166.3 | 135.8(DMB-C5N) | ||
| C4N | 113.1 | 111.8 | 139.5(DMB-C9N) | |||
| C5N | 160.7 | 161.5 | 132.8(DMB-C8N) | |||
| C6N | 155.1 | 155.7 | 114.3(DMB-C7N) | |||
| C8N | 7.06 | 147.7 | 7.03 | 147.7 | 7.10 | 144.7(DMB-C2N) |
| C21N | 2.26 | 28.4 | 2.16 | 22.8(DMB-C10N) | ||
a
1H NMR, δ with δ(H2O)int = 4.67 ppm; 13C NMR, δ with δ(TSP)ext = 0.0 ppm. NM, not measured.
b
All chemical shifts are from Calafat and Marzilli (16). 1H chemical shifts are referenced to H2O by subtracting 0.11 ppm to the reported values (relative to TSP).
c
31P-13C couplings: 1, JCP = 4.8 Hz; 2, JCP = 6.2 Hz; 3, JCP no information because of signal overlap; 4, JCP < 1 Hz; 5, JCP = 2.8 Hz; 6, JCP = 7.0 Hz.