Basicity of the amino groups of the aminoglycoside amikacin using capillary electrophoresis and coupled CE-MS-MS techniques

被引：31

作者：

Kane, RS

Glink, PT

Chapman, RG

McDonald, JC

Jensen, PK

Gao, HY

Pasa-Tolic, L

Smith, RD

Whitesides, GM

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

[2] Pacific NW Natl Lab, Environm Mol Sci Lab, Richland, WA 99352 USA

来源：

ANALYTICAL CHEMISTRY | 2001年 / 73卷 / 16期

关键词：

D O I：

10.1021/ac010173m

中图分类号：

O65 [分析化学];

学科分类号：

070302 ; 081704 ;

摘要：

This paper describes the use of capillary electrophoresis (CE), and coupled CE and mass spectrometric techniques, to measure the values of the pK(a) of the amino groups of the aminoglycoside antibiotic amikacin and of its acetylated derivatives. These values of pK(a) (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 C-13 and (NNMR)-N-15 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.

引用

收藏

页码：4028 / 4036

页数：9

相关论文

共 18 条

[1] ''Colored'' noise waveforms and quadrupole excitation for the dynamic range expansion of Fourier transform ion cyclotron resonance mass spectrometry [J].

Bruce, JE ;

Anderson, GA ;

Smith, RD .

ANALYTICAL CHEMISTRY, 1996, 68 (03) :534-541

[2] Long-range electrostatic contributions to protein-ligand binding estimated using protein charge ladders, affinity capillary electrophoresis, and continuum electrostatic theory [J].

Caravella, JA ;

Carbeck, JD ;

Duffy, DC ;

Whitesides, GM ;

Tidor, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4340-4347

[3] Correlations between the charge of proteins and the number of ionizable groups they incorporate: Studies using protein charge ladders, capillary electrophoresis, and Debye-Huckel theory [J].

Carbeck, JD ;

Colton, IJ ;

Anderson, JR ;

Deutch, JM ;

Whitesides, GM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (46) :10671-10679

[4] Formation of protein charge ladders by acylation of amino groups on proteins [J].

Colton, IJ ;

Anderson, JR ;

Gao, JM ;

Chapman, RG ;

Isaacs, L ;

Whitesides, GM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (52) :12701-12709

[5] Noncovalent polycationic coatings for capillaries in capillary electrophoresis of proteins [J].

Cordova, E ;

Gao, JM ;

Whitesides, GM .

ANALYTICAL CHEMISTRY, 1997, 69 (07) :1370-1379

[6] Biologically important conformations of aminoglycoside antibiotics bound to an aminoglycoside 3'-phosphotransferase as determined by transferred nuclear Overhauser effect spectroscopy [J].

Cox, JR ;

Serpersu, EH .

BIOCHEMISTRY, 1997, 36 (09) :2353-2359

[7] Structure of the A site of Escherichia coli 16S ribosomal RNA complexed with an aminoglycoside antibiotic [J].

Fourmy, D ;

Recht, MI ;

Blanchard, SC ;

Puglisi, JD .

SCIENCE, 1996, 274 (5291) :1367-1371

[8] Determination of intramolecular hydrogen bonds in amikacin in water solution by NMR spectroscopy [J].

Gaggelli, E ;

Gaggelli, N ;

Maccotta, A ;

Valensin, G ;

Marini, D ;

DiCocco, ME ;

Delfini, M .

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 1995, 51 (11) :1959-1963

[9] DETERMINATION OF THE EFFECTIVE CHARGE OF A PROTEIN IN SOLUTION BY CAPILLARY ELECTROPHORESIS [J].

GAO, JM ;

GOMEZ, FA ;

HARTER, R ;

WHITESIDES, GM .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (25) :12027-12030

[10] USING CAPILLARY ELECTROPHORESIS TO FOLLOW THE ACETYLATION OF THE AMINO-GROUPS OF INSULIN AND TO ESTIMATE THEIR BASICITIES [J].

GAO, JM ;

MRKSICH, M ;

GOMEZ, FA ;

WHITESIDES, GM .

ANALYTICAL CHEMISTRY, 1995, 67 (18) :3093-3100