TY - JOUR
T1 - Multinuclear Nuclear Magnetic Resonance Spectroscopy Is Used to Determine Rapidly and Accurately the Individual pKa Values of 2-Deoxystreptamine, Neamine, Neomycin, Paromomycin, and Streptomycin
AU - Alkhzem, Abdulaziz H.
AU - Woodman, Timothy J.
AU - Blagbrough, Ian S.
PY - 2021/2/2
Y1 - 2021/2/2
N2 - Unambiguous assignments have been made for each individual pKa value of the amino group and guanidine substituents on 2-deoxystreptamine, neamine, neomycin, paromomycin, and streptomycin by pH-titration evaluation of their 1H, 13C, and 15N (by 1H-15N heteronuclear multiple-bond correlation (HMBC) spectra) NMR chemical shifts (δXs) as the reporter nuclei. These data require minor revisions of the literature data in terms of the assignment order for neomycin and paromomycin. In situ titrations and NMR spectroscopy are shown to be a powerful combination for rapidly (minutes) obtaining each distinct pKa value of the similar amine and guanidine functional groups, which decorate aminoglycoside antibiotics.
AB - Unambiguous assignments have been made for each individual pKa value of the amino group and guanidine substituents on 2-deoxystreptamine, neamine, neomycin, paromomycin, and streptomycin by pH-titration evaluation of their 1H, 13C, and 15N (by 1H-15N heteronuclear multiple-bond correlation (HMBC) spectra) NMR chemical shifts (δXs) as the reporter nuclei. These data require minor revisions of the literature data in terms of the assignment order for neomycin and paromomycin. In situ titrations and NMR spectroscopy are shown to be a powerful combination for rapidly (minutes) obtaining each distinct pKa value of the similar amine and guanidine functional groups, which decorate aminoglycoside antibiotics.
U2 - 10.1021/acsomega.0c05138
DO - 10.1021/acsomega.0c05138
M3 - Article
SN - 2470-1343
VL - 6
SP - 2824
EP - 2835
JO - ACS OMEGA
JF - ACS OMEGA
IS - 4
ER -