Table 3.
NMR data of products from reaction with YgbB protein
| Position | Chemical shifts,
ppm
|
Coupling constants, Hz
|
|||||
|---|---|---|---|---|---|---|---|
| 1H* | 13C† | 31P‡ | JHH | JPC | JPP | JCC | |
| 2C-methyl-d-erythritol 2,4-cyclodiphosphate (8) | |||||||
| 1 | 3.51 (d, 1) | 66.95 | 12.2 (/1§) | 41.8 (2)¶∥ | |||
| 1§ | 3.66 (d, 1) | 12.2 (1) | |||||
| 2 | 83.87 | 8.4 (P-2)∥ | 39.8 (2-Me)¶∥ | ||||
| 2-Me | 1.31 (s, 3) | 16.30 | 5.3 (P-2)∥ | 39.8 (2)¶∥ | |||
| 3 | 4.01 (m, 1) | 68.42 | ND | ND | 46.0 (2)¶ | ||
| 4 | 4.02 (m, 1) | 65.72 | ND | 6.6 (P-4)** | 42.7 (3)¶ | ||
| 4§ | 4.07 (m, 1) | ND | |||||
| P-4 | −7.65 | 23.6 (P-2) | |||||
| P-2 | −11.66 | 8.5 (2)∥, 5.3 (2-Me)∥ | 23.6 (P-4) | ||||
| 2C-methyl-d-erythritol 3,4-cyclomonophosphate (7) | |||||||
| 1 | 3.38 (d, 1) | 65.64 | 12.0 (1§) | ||||
| 1§ | 3.47 (d, 1) | 12.0 (1) | |||||
| 2 | 73.02 | 6.5∥ | |||||
| 2-Me | 1.09 (s, 3) | 17.73 | |||||
| 3 | 4.15 (m, 1) | 77.61 | 1.7∥ | ||||
| 4 | 4.18 (m, 1) | 64.96 | 1.1∥ | ||||
| 4§ | 4.34 (ddd, 1) | 11.2 (4), 3.8, 7.2 (3) | |||||
| P | 21.67 (s) | ||||||
*
Referenced to external trimethylsilylpropane sulfonate. The multiplicities and the relative integral values of 1H NMR signals of an unlabeled sample are indicated in parentheses.
†Referenced to external trimethylsilylpropane sulfonate.
‡Referenced to external phosphoric acid (85%, vol/vol).
§Indicates one of diastereotopic hydrogens bonded to the respective index carbon.
¶From the reaction with [1,2,2-methyl,3,4-13C5] 4-diphosphocytidyl-2C-methyl-d-erythritol 2-phosphate.
∥From the reaction with [2,2-methyl-13C2]4-diphosphocytidyl-2C-methyl-d-erythritol 2-phosphate.
**From the reaction with [1,3,4-13C1]4-diphosphocytidyl-2C-methyl-d-erythritol 2-phosphate.