TABLE 1.
400.13 MHz 1H and 100.62 MHz 13C NMR chemical shift data (in ppm) and J coupling constants of the rhamnosyl oligosaccharides (III, V, VII, and IV)
Chemical shift data were measured at 297 K for solutions in D2O. 13C NMR data were obtained from a proton-decoupled one-dimensional spectrum for compounds III, IV, and V and from HSQC spectra of compound VII.
|
Carbohydrate signals |
Octyl |
||||||||
|---|---|---|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | 6 | 1 | 2 | CH3 | |
| Compound III | |||||||||
| A →3)-β-d-Galp-(1 → | |||||||||
| 1H | 4.42 | 3.61 | 3.68 | 4.00 | 3.70 | 3.77/3.73 | 3.89/3.67 | 1.62 | 0.85 |
| JH,H (Hz) | (7.8) | (9.9) | 81.36 | (3.1, 1.0) | 75.83 | 61.63 | 71.46 | 29.51 | 14.19 |
| 13C | 103.32 | 70.89a | 69.23 | ||||||
| B →3)-α-l-Rhap-(1 → | |||||||||
| 1H | 5.00 | 4.15 | 3.89 | 3.54 | 3.80 | 1.28 | |||
| JH,H (Hz) | (1.8) | (3.1) | (9.7) | (9.7) | 70.12 | (6.2) | |||
| 13C | 103.05 | 70.67 | 79.15 | 72.08 | 17.46b | ||||
| C α-l-Rhap-(1 → | |||||||||
| 1H | 5.04 | 4.06 | 3.84 | 3.45 | 3.80 | 1.29 | |||
| JH,H (Hz) | (1.7) | (3.3) | (9.7) | (9.6) | 69.93 | (6.3) | |||
|
13C
|
103.22
|
70.96a |
70.96a |
72.81
|
17.38b |
||||
| Compound V | |||||||||
| A →3)-β-d-Galp-(1 → | |||||||||
| 1H | 4.43 | 3.61 | 3.68 | 4.00 | 3.69 | 3.78-3.72 | 3.94/3.68 | 1.65-1.58 | 0.85 |
| JH,H (Hz) | (7.6) | (9.6) | 81.38 | (3.2) | 75.84 | 61.63 | 71.47 | 29.57 | 14.19 |
| 13C | 103.32 | 70.89a | 69.24 | ||||||
| B →3)-α-l-Rhap-(1 → | |||||||||
| 1H | 5.02b | 4.14c | 3.90 | 3.56d | 3.88-3.82 | 1.29c | |||
| JH,H (Hz) | (2.0) | (3.6) | (9.6) | (9.6) | 70.12 | (6.2) | |||
| 13C | 103.05f | 70.76a | 79.17 | 72.08 | 17.44 | ||||
| C →3)-α-l-Rhap-(1 → | |||||||||
| 1H | 5.01b | 4.17c | 3.90 | 3.54d | 3.92-3.88 | 1.28e | |||
| JH,H (Hz) | (2.0) | (3.2) | (9.6) | (9.6) | 70.12 | 17.44g | |||
| 13C | 103.26f | 70.96a | 79.17 | 72.08 | |||||
| D α-l-Rhap-(1 → | |||||||||
| 1H | 5.04 | 4.07 | 3.84 | 3.46 | NDh | 1.29e | |||
| JH,H (Hz) | (1.6) | (3.2) | (9.6) | (9.6) | 69.93 | 17.37g | |||
|
13C
|
100.82
|
70.96a |
70.65a |
72.79
|
|||||
| Compound VII | |||||||||
| A →3)-β-d-Galp-(1 → | |||||||||
| 1H | 4.40 | 3.55 | 3.66 | 3.97 | ∼3.66 | ∼3.70 | 3.83/3.64 | 1.59 | 0.82 |
| JH,H (Hz) | (7.6) | (9.6) | 81.5 | (2.9, 1.0) | 75.9 | 61.7 | 71.5 | 29.5 | 14.8 |
| 13C | 103.4 | 70.7 | 69.3 | ||||||
| B →3)-α-l-Rhap-(1 → | |||||||||
| 1H | 4.97 | 4.10 | 3.76 | 3.52 | 3.80-3.89 | 1.26c | |||
| JH,H (Hz) | (1.6) | (3.3) | (10.1) | (10.1) | ND | (6.0) | |||
| 13C | 103.1 | 70.7 | 79.1 | 72.5 | 17.4 | ||||
| C →2)-α-l-Rhap-(1 → | |||||||||
| 1H | 5.17 | 4.03 | 3.91 | 3.45 | 3.80-3.89 | 1.25c | |||
| JH,H (Hz) | (1.6) | (3.2) | (9.8) | (9.9) | ND | (6.1) | |||
| 13C | 101.7 | 78.5 | 70.0 | 73.0 | 17.4 | ||||
| D α-l-Rhap-(1 → | |||||||||
| 1H | 4.92 | 4.03 | 3.86 | 3.40 | 3.63 | 1.22 | |||
| JH,H (Hz) | (1.6) | (3.2) | (9.6) | (9.6) | 70.6 | (6.4) | |||
|
13C
|
103.1
|
71.0
|
71.0
|
73.0
|
17.4
|
||||
| Compound IV | |||||||||
| A →3)-β-d-Galp-(1 → | |||||||||
| 1H | 4.43 | 3.59 | 3.68 | 4.01 | 3.70 | 3.75/3.65 | 3.92/3.67 | 1.59 | 0.82 |
| JH,H (Hz) | (7.8) | (9.9) | 81.45 | (3.0, 1.0) | 75.74 | 61.51 | 71.37b | 29.41 | 14.11 |
| 13C | 103.20 | 70.86a | 69.12 | ||||||
| JC,H (Hz) | (163.8) | ||||||||
| B →2)-α-l-Rhap-(1 → | |||||||||
| 1H | 5.14 | 4.25 | 3.84 | 3.48 | 3.84 | 1.28 | |||
| JH,H (Hz) | (1.5) | (3.5) | (9.8) | (9.7) | 70.04c | (6.3) | |||
| 13C | 100.74 | 79.14 | 70.16c | 73.01d | 17.28 | ||||
| JC,H (Hz) | (172.5) | ||||||||
| C β-l-Rhap-(1 → | |||||||||
| 1H | 4.70 | 4.01 | 3.58 | 3.38 | 3.38 | 1.31 | |||
| JH,H (Hz) | (1.5) | (3.3) | 71.61 | (9.5) | 72.91d | (5.7) | |||
| 13C | 99.13 | 70.69a | 72.61d | 17.28 | |||||
| JC,H (Hz) | (160.5) | ||||||||
a
Assignments are interchangeable.
b
Assignments are interchangeable.
c
Assignments are interchangeable.
d
ND, not determined.