Table 2.
Calculated degree of sulfation (DS) for reaction product mixtures afforded by O-sulfonation of N-cbz kanamycin (A), N-cbz apramycin (B and D), and N-cbz neomycin (C). Two different sulfating reagents were employed, Py·SO3 and ClSO3H. The percent at each sulfated state is expressed as %DS and the number of sulfates per molecule
| Rxn | Starting Material | Sulf Method | avg DS |
% DS 7SO4 |
% DS 6SO4 |
% DS 5SO4 |
% DS 4SO4 |
|---|---|---|---|---|---|---|---|
| A | N-cbz kanamycin | PySO3 | 6.0 | 17.8 | 66.0 | 16.2 | -- |
| B | N-cbz apramycin | PySO3 | 4.9 | NA | 18.4 | 55.5 | 26.1 |
| C | N-cbz neomycin | ClSO3H | 7 | 100 | -- | -- | -- |
| D | N-cbz apramycin | ClSO3H | 6 | NA | 100 | -- | -- |
[a]
NA, not applicable
[b]
--, below limit of detection