Basicity of the amino groups of the aminoglycoside amikacin using capillary electrophoresis and coupled CE-MS-MS techniques.
This paper describes the use of capillary electrophoresis (CE), and coupled CE and mass spectrometric techniques, to measure the values of the pKa of the amino groups of the aminoglycoside antibiotic amikacin and of its acetylated derivatives. These values of pKa (8.4, 6.7, 9.7, 8.4) were determined by measuring the electrophoretic mobilities of the molecules as a function of pH; they are within 0.7 unit of certain values reported in the literature (by 13C and 15N NMR spectroscopies) but resolved ambiguities left by these earlier studies. The range of values of pKa of amino groups also indicates the complex dependence of the acidity of a functional group (and thus the extent of ionization at a specified value of pH) on the molecular environment of that group.
Kane
R S
RS
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Glink
P T
PT
Chapman
R G
RG
McDonald
J C
JC
Jensen
P K
PK
Gao
H
H
Pasa-Tolić
L
L
Smith
R D
RD
Whitesides
G M
GM
D000107:Acetylation; D000583:Amikacin / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D019075:Electrophoresis, Capillary / Q000379:methods*; D006863:Hydrogen-Ion Concentration; D013058:Mass Spectrometry / Q000379:methods; D008969:Molecular Sequence Data; D017550:Spectroscopy, Fourier Transform Infrared
D000588:Amines; D000900:Anti-Bacterial Agents; D000583:Amikacin