Table 3. pKa Values of Individual Nitrogen Atoms of Amikacin Determined Using 1H, 13C, and 15N HMBC NMR Spectroscopy in This Work and Then Compared with the Published Data, as Indicated.
individual nitrogen atoms pKa |
||||
---|---|---|---|---|
method | N-3 | N-6′ | N-3″ | N-4‴ |
15N NMRa | 7.62 | 8.92 | 8.13 | 9.70 |
1H NMRb | 7.70 | 8.93c | 8.05 | 9.92 |
13C NMRb | 7.63 | 8.70 | 8.00 | 9.85 |
15N HMBC NMRb | 7.60 | 8.80 | 8.10 | 9.90 |
pKa values of individual nitrogen atoms of amikacin determined using 15N NMR spectroscopy in H2O/D2O (85:15 v/v) relative to 15NH4Cl at 25 °C.16
This work.
The pKa value of N-6′ of amikacin determined using 1H NMR spectroscopy (in this work) is the average pKa of the values of N-6′ obtained using 1H NMR spectroscopic data for 6′a (8.90) and 6′b (8.96).