Table 1.
Chemical shifts of carbon and proton signals of carbohydrate moieties of compound 4, the corresponding isolated derivative and glycopeptide 5.a
| Synthetic trisaccharide 4 | Yoshida-Moriguchi et al. | Glycopeptide 5 | ||||
|---|---|---|---|---|---|---|
| H1 | C13 | H1 | C13 | H1 | C13 | |
| A1 | 3.61,3.86 | 65.85 | 3.63,3.87 | 65.80 | 4.95 | 104.15 |
| A2 | 3.90 | 73.18 | 3.92 | 73.10 | 3.85 | 72.37 |
| A3 | 3.67 | 71.93 | 3.68 | 71.90 | 3.82 | 71.71 |
| A4 | 4.00 | 78.76 | 4.02 | 78.70 | 3.90 | 79.17 |
| A5 | 3.82 | 71.90 | 3.89 | 71.70 | 3.81 | 73.15 |
| A6 | 3.87,4.01 | 67.66 | 3.92,4.06 | 68.30 | 3.98 | 65.32 |
| B1 | 4.68 | 103.53 | 4.64 | 103.50 | 4.61 | 103.96 |
| B2 | 3.83 | 57.14 | 3.85 | 57.11 | 3.86 | 56.98 |
| B3 | 3.71 | 83.68 | 3.76 | 83.60 | 3.80 | 83.50 |
| B4 | 3.47 | 71.87 | 3.49 | 71.80 | 3.52 | 73.38 |
| B5 | 3.55 | 77.47 | 3.54 | 77.50 | 3.57 | 77.98 |
| B6 | 3.69, 3.92 | 63.79 | 3.71, 3.94 | 63.80 | 3.69,3.76 | 63.44 |
| C1 | 4.48 | 104.29 | 4.49 | 104.20 | 4.50 | 104.20 |
| C2 | 3.83 | 55.23 | 3.84 | 55.21 | 3.84 | 55.26 |
| C3 | 3.72 | 73.18 | 3.74 | 73.20 | 3.73 | 73.25 |
| C4 | 3.90 | 70.39 | 3.91 | 70.40 | 3.91 | 70.45 |
| C5 | 3.69 | 77.70 | 3.69 | 77.70 | 3.68 | 77.69 |
| C6 | 3.74 | 63.64 | 3.77 | 63.80 | 3.75 | 63.70 |
a
1H-13C HMQC NMR correlation spectra of compound 4 and the corresponding isolated derivative are presented in the supporting information (Figure SI 1). Letters refer to the sugar residues proceeding from the reducing end, A=Man, B=GlcNAc and C=GalNAc, with the associated numbers referring to the carbon atom involved.