Polarographic and Voltammetric Behavior of the Antibiotic Cefetamet; Reduction of the Methoxyimino Group

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Title:Polarographic and Voltammetric Behavior of the Antibiotic Cefetamet; Reduction of the Methoxyimino Group
Creators:
Aleksić, Mara
Kapetanović, Vera
Zuman, Petr
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 7, pp. 1429-1442
Uncontrolled Keywords:Oximino group, Cephalosporins, Antibiotics, Electrochemistry, Cefetamet, Polarography, Voltammetry, Electroreduction

Abstract

Evaluation of DC polarographic <i>i</i>-<i>E</i> curves and analogous curves obtained by cyclic voltammetry in aqueous buffers as well as in buffers containing 30% v/v ethanol indicated that the methoxyimino group of cefetamet is reduced on DME and HDME in the following way: the methoxyimino group can be at the electrode surface rapidly protonated up to pH about 9. In the protonated form of the grouping (&gt;C=NH-OCH<sub>3</sub>)<sup>+</sup>, the OCH<sub>3</sub> is cleaved off in the first two-electron step. The resulting imine is in equilibrium with its protonated form, which is reduced in a second two-electron step. At pH higher than about 10, the unprotonated form of the methoxyimino group is reduced in a single four-electron step to amine. Studies using cyclic voltammetry were complicated by adsorption phenomena. <p>

Title:Polarographic and Voltammetric Behavior of the Antibiotic Cefetamet; Reduction of the Methoxyimino Group
Creators:
Aleksić, Mara
Kapetanović, Vera
Zuman, Petr
Uncontrolled Keywords:Oximino group, Cephalosporins, Antibiotics, Electrochemistry, Cefetamet, Polarography, Voltammetry, Electroreduction
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:69
Number:7
Page Range:pp. 1429-1442
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20041429UNSPECIFIED
ID Code:2282
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Aleksić, Mara; Kapetanović, Vera; Zuman, Petr (2004) Polarographic and Voltammetric Behavior of the Antibiotic Cefetamet; Reduction of the Methoxyimino Group. Collection of Czechoslovak Chemical Communications, 69 (7). pp. 1429-1442. ISSN 0010-0765

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