Abstract
Bile acids and sterols in general have long been considered practically inactive for direct redox processes. Herein, a novel way of electrochemical oxidation of primary bile acids is reported, involving an initial acid-induced dehydration step, as confirmed by capillary electrophoresis–mass spectrometry, thereby extending the electrochemical activity of the steroid core. Oxidation potentials were found to be ca + 1.2 V vs. Ag/AgNO3 in acetonitrile on boron doped diamond, glassy carbon, and platinum electrodes in a mixed acetonitrile–aqueous medium employing perchloric acid as a chemical reagent, and as a supporting electrolyte for the voltammetric measurements. The chemical step proved to be effective only for primary bile acids, possessing an axial 7α-hydroxyl group, which is a prerequisite for providing a well-developed voltammetric signal. Preliminary results show that other steroids, e.g., cholesterol, can also be oxidized by employing a similar approach.
| Original language | English |
|---|---|
| Pages (from-to) | 99-103 |
| Number of pages | 5 |
| Journal | Electrochemistry Communications |
| Volume | 86 |
| DOIs | |
| Publication status | Published - 1 Jan 2018 |
| Externally published | Yes |
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Keywords
- Bare electrode
- Bile acids
- Electrochemical oxidation
- Steroid dehydration
- Voltammetry
ASJC Scopus subject areas
- Electrochemistry
Cite this
Bile acids : Electrochemical oxidation on bare electrodes after acid-induced dehydration. / Klouda, Jan; Barek, Jiří; Kočovský, Pavel; Herl, Thomas; Matysik, Frank Michael; Nesměrák, Karel; Schwarzová-Pecková, Karolina.
In: Electrochemistry Communications, Vol. 86, 01.01.2018, p. 99-103.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Bile acids
T2 - Electrochemical oxidation on bare electrodes after acid-induced dehydration
AU - Klouda, Jan
AU - Barek, Jiří
AU - Kočovský, Pavel
AU - Herl, Thomas
AU - Matysik, Frank Michael
AU - Nesměrák, Karel
AU - Schwarzová-Pecková, Karolina
PY - 2018/1/1
Y1 - 2018/1/1
N2 - Bile acids and sterols in general have long been considered practically inactive for direct redox processes. Herein, a novel way of electrochemical oxidation of primary bile acids is reported, involving an initial acid-induced dehydration step, as confirmed by capillary electrophoresis–mass spectrometry, thereby extending the electrochemical activity of the steroid core. Oxidation potentials were found to be ca + 1.2 V vs. Ag/AgNO3 in acetonitrile on boron doped diamond, glassy carbon, and platinum electrodes in a mixed acetonitrile–aqueous medium employing perchloric acid as a chemical reagent, and as a supporting electrolyte for the voltammetric measurements. The chemical step proved to be effective only for primary bile acids, possessing an axial 7α-hydroxyl group, which is a prerequisite for providing a well-developed voltammetric signal. Preliminary results show that other steroids, e.g., cholesterol, can also be oxidized by employing a similar approach.
AB - Bile acids and sterols in general have long been considered practically inactive for direct redox processes. Herein, a novel way of electrochemical oxidation of primary bile acids is reported, involving an initial acid-induced dehydration step, as confirmed by capillary electrophoresis–mass spectrometry, thereby extending the electrochemical activity of the steroid core. Oxidation potentials were found to be ca + 1.2 V vs. Ag/AgNO3 in acetonitrile on boron doped diamond, glassy carbon, and platinum electrodes in a mixed acetonitrile–aqueous medium employing perchloric acid as a chemical reagent, and as a supporting electrolyte for the voltammetric measurements. The chemical step proved to be effective only for primary bile acids, possessing an axial 7α-hydroxyl group, which is a prerequisite for providing a well-developed voltammetric signal. Preliminary results show that other steroids, e.g., cholesterol, can also be oxidized by employing a similar approach.
KW - Bare electrode
KW - Bile acids
KW - Electrochemical oxidation
KW - Steroid dehydration
KW - Voltammetry
UR - http://www.scopus.com/inward/record.url?scp=85037137162&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85037137162&partnerID=8YFLogxK
U2 - 10.1016/j.elecom.2017.11.024
DO - 10.1016/j.elecom.2017.11.024
M3 - Article
AN - SCOPUS:85037137162
VL - 86
SP - 99
EP - 103
JO - Electrochemistry Communications
JF - Electrochemistry Communications
SN - 1388-2481
ER -