Individual p K a Values of Tobramycin, Kanamycin B, Amikacin, Sisomicin, and Netilmicin Determined by Multinuclear NMR Spectroscopy

ACS Omega. 2020 Aug 11;5(33):21094-21103. doi: 10.1021/acsomega.0c02744. eCollection 2020 Aug 25.

Abstract

NMR spectroscopy is a powerful technique for separating and measuring each distinct pK a value of the amino groups around aminoglycoside antibiotics. Unambiguous assignments were made for each individual amine substituent on 2-deoxystreptamine, tobramycin, kanamycin B, amikacin, sisomicin, and netilmicin using variations in the NMR spectroscopic chemical shift (δ) with 1H, 13C, and 15N HMBC; the individual pK a values of netilmicin are reported for the first time.