Table 3.
NMR data of 4-diphosphocytidyl-2C-methyl-d-erythritol 2-phosphate
| Position | Chemical
shifts, ppm
|
Coupling constants,
Hz
|
Correlation
pattern
|
|||||||
|---|---|---|---|---|---|---|---|---|---|---|
| 1H† | 13C‡ | 31P§ | JHH | JPC | JPP | JCC | DOF-COSY | HMBC¶ | INADEQUATE†† | |
| 1 | 3.58(m,1) | 65.78 | 3.8∥(P-2) | 39.8††(2) | 1* | 2 | ||||
| 1* | 3.64(m,1) | 1 | ||||||||
| 2 | 81.91 | 7.4¶(P-2) | 38.9¶(2-me) | 2-methyl,1,3 | 1,2-methyl,3 | |||||
| 2-methyl | 1.26(s,3) | 17.92 | 1.9¶(P-2) | 38.9¶(2) | 1,3 | 2 | ||||
| 3 | 3.81(m,1) | 73.96 | 7.3∥(P-2,P-4) | 4,4* | 2,4 | |||||
| 4 | 3.89(m,1) | 67.16 | 5.7|(P-4) | 42.9††(3) | 3,4* | 3 | ||||
| 4* | 4.19(m,1) | 3,4 | ||||||||
| 1′ | 5.87(d,1) | 90.21 | 4.4 | 2′ | Cyt-6 | |||||
| 2′ | 4.21(t,1) | 75.24 | 4.9 | 1′,3′ | ||||||
| 3′ | 4.25(t,1) | 70.22 | 4.9 | 2′,4′ | ||||||
| 4′ | 4.17(m,1) | 83.85 | 3′,5′ | |||||||
| 5′ | 4.09(ddd,1) | 65.49 | 12.2,5.4 | 4′,5′* | ||||||
| 5′* | 4.17(m,1) | 5′ | ||||||||
| Cyt-2 | 156.50 | Cyt-6 | ||||||||
| Cyt-4 | 165.49 | Cyt-5,Cyt-6 | ||||||||
| Cyt-5 | 6.07(d,1) | 97.35 | 7.6 | Cyt-6 | Cyt-6 | |||||
| Cyt-6 | 7.92(d,1) | 143.03 | 7.6 | Cyt-5 | Cyt-5 | |||||
| P(2) | 0.49 | 1.7¶(2-me),7.6¶(2) | ||||||||
| P(4) | −7.28 | 20.8 | ||||||||
| P(5′) | −8.00 | 20.8 | ||||||||
*
Indicates downfield shifted 1H NMR signals of diastereotopic hydrogen pairs.
† 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).
¶ From the spectrum of [2,2-methyl-13C2]4-diphosphocytidyl-2C-methyl-d-erythritol 2-phosphate.
∥ From the spectrum of [1,3,4-13C1]4-diphosphocytidyl-2C-methyl-d-erythritol 2-phosphate.
†† From the spectrum of [1,2,2-methyl,3,4-13C5]4-diphosphocytidyl-2C-methyl-d-erythritol 2-phosphate.