A selective electrochemical method of glycosylation of 3β-hydroxy-Δ5-steroids

Morzycki, Jacek W.; Łotowski, Zenon; Siergiejczyk, Leszek; Wałejko, Piotr; Witkowski, Stanisław; Kowalski, Jan; Płoszyńska, Jolanta; Sobkowiak, Andrzej

doi:10.1016/j.carres.2010.03.018

Cited by 11 publications

(4 citation statements)

References 34 publications

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“…Because the current response was not very stable and the noise was quite significant at 1.6 V potential, we settled on 1.5 V to be used for further experiments. This value compared well with other applied potentials for direct electrooxidation of cholesterol reported in the literature such as 1.9 V [ 22 , 34 ] or 1.5 V [ 23 ].…”

Section: Resultssupporting

confidence: 84%

“…Although cholesterol has been regarded as an electrochemically inactive compound [ 21 ], recent studies [ 22 , 23 ] show that direct electrochemical oxidation of cholesterol is also possible and affords different products depending on the reaction condition. The first direct electrochemical oxidation of cholesterol was performed in glacial acetic acid on a platinum anode under constant current in a divided cell [ 22 ].…”

Section: Introductionmentioning

confidence: 99%

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Innovative Non-Enzymatic Electrochemical Quantification of Cholesterol

Carp¹,

Pinteala²,

Arvinte³

2022

Sensors

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The use of the Liebermann–Burchard reaction in this study has been explored in the development of a simple, reliable, and robust quantitative electrochemical method to assay cholesterol, and hence provide a good alternative to colorimetric methods. The optimization of batch mode operation for electrochemical oxidation of cholesterol in the Liebermann–Burchard reagents included the applied potential and acidic volume. Tested using chronoamperometry, the developed method showed a high sensitivity (14.959 μA mM−1) and low detection limit (19.78 nM) over a 0.025–3 mM concentration range, with remarkable linearity (R2  =  0.999), proving an analytical performance either higher or comparable to most of the cholesterol sensors discussed in literature. The influence of possible interfering bioactive agents, namely, glucose, uric acid, ascorbic acid, KCl and NaCl, has been evaluated with no or negligible effects on the measurement of cholesterol. Our study was directed at finding a new approach to chemical processing arising from the use of external potential as an additional level of control for chemical reactions and the transfer of electrons between surfaces and molecules. Finally, the optimized method was successfully applied for the determination of cholesterol content in real blood samples.

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Section: Resultssupporting

confidence: 84%

Section: Introductionmentioning

confidence: 99%

Innovative Non-Enzymatic Electrochemical Quantification of Cholesterol

Carp¹,

Pinteala²,

Arvinte³

2022

Sensors

View full text Add to dashboard Cite

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“…The formation of byproducts was diminished with this system. The presented system proved suitable for the electrochemical glycosylation of 3β-hydroxy-Δ 5 -steroids [ 43 ]. In this case, 2,3,4,6-tetra- O -acetyl-D-glucopyranose was used as a nucleophile ( Scheme 10 ).…”

Section: Reviewmentioning

confidence: 99%

Electrochemical oxidation of cholesterol

Morzycki¹,

Sobkowiak²

2015

Beilstein J. Org. Chem.

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SummaryIndirect cholesterol electrochemical oxidation in the presence of various mediators leads to electrophilic addition to the double bond, oxidation at the allylic position, oxidation of the hydroxy group, or functionalization of the side chain. Recent studies have proven that direct electrochemical oxidation of cholesterol is also possible and affords different products depending on the reaction conditions.

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“…During anodic oxidation of cholesterol in dichloromethane (the choice of solvent is crucial as the reaction course may be different in other solvents) [ 1 ], splitting of the carbon–oxygen bond in an intermediate radical cation occurs, thus leading to a mesomerically stabilized homoallylic carbocation and a hydroxyl radical ( Scheme 1 ) [ 2 ]. However, the glycosylation reaction was not very efficient due to competition between the sugar alcohol and cholesterol for the carbocation [ 3 ]. If cholesterol wins the competition, the dimer 2 (dicholesteryl ether) is formed.…”

Section: Introductionmentioning

confidence: 99%

3α,5α-Cyclocholestan-6β-yl ethers as donors of the cholesterol moiety for the electrochemical synthesis of cholesterol glycoconjugates

Tomkiel¹,

Biedrzycki²,

Płoszyńska³

et al. 2015

Beilstein J. Org. Chem.

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Summary3α,5α-Cyclocholestan-6β-yl alkyl and aryl ethers were proved to be efficient cholesteryl donors in the electrochemical synthesis of glycoconjugates. 3α,5α-Cyclocholestan-6β-ol (i-cholesterol) and its tert-butyldimethylsilyl ether can also be used for this purpose. The i-cholesterol derivatives show similar reactivities to those of previously studied 3α,5α-cyclocholestan-6β-thioethers.

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A selective electrochemical method of glycosylation of 3β-hydroxy-Δ5-steroids

Cited by 11 publications

References 34 publications

Innovative Non-Enzymatic Electrochemical Quantification of Cholesterol

Innovative Non-Enzymatic Electrochemical Quantification of Cholesterol

Electrochemical oxidation of cholesterol

3α,5α-Cyclocholestan-6β-yl ethers as donors of the cholesterol moiety for the electrochemical synthesis of cholesterol glycoconjugates

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