Electrochemical oxidation of cholesterol

Morzycki, Jacek W.; Sobkowiak, Andrzej

doi:10.3762/bjoc.11.45

Cited by 31 publications

(20 citation statements)

References 72 publications

(65 reference statements)

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“…Moreover, the hydroxyl groups of cholesterol may be oxidized to ketonic groups by the QD nanocomposite and adsorbed on the surface of the nanocomposite. 53 , 68 − 70 …”

Section: Resultsmentioning

confidence: 99%

Nanocomposite of CuInS/ZnS and Nitrogen-Doped Graphene Quantum Dots for Cholesterol Sensing

et al. 2021

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In this paper, nitrogen graphene quantum dots (N-GQDs) and copper indium sulfide/zinc sulfide (CIS/ZnS) QDs were synthesized via facile hydrothermal and aqueous solution routes, respectively. Herein, a fluorescent nanocomposite has been synthesized between N-GQDs and CIS/ZnS QDs in an aqueous phase. This nanocomposite was characterized by photoluminescence, Raman, and ultraviolet–visible (UV–vis) spectroscopies, high-resolution transmission electron microscopy (HRTEM), and X-ray diffraction (XRD). This fluorescent nanocomposite was developed as a highly sensitive, selective nonenzymatic cholesterol optical biosensor in 0.312–5 mM cholesterol. HRTEM micrographs confirmed the preparation of CIS/ZnS QDs and N-GQDs with average diameters of 3 and 5 nm, respectively. The as-prepared NG/CIS/ZnS QD nanocomposite had a high sensitivity for cholesterol with a wide linear range of concentration of 0.312–5 mM with an excellent correlation coefficient (R 2) of 0.9688 and limit of detection (LOD) of 0.222 mM.

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“…Moreover, the hydroxyl groups of cholesterol may be oxidized to ketonic groups by the QD nanocomposite and adsorbed on the surface of the nanocomposite. 53 , 68 − 70 …”

Section: Resultsmentioning

confidence: 99%

Nanocomposite of CuInS/ZnS and Nitrogen-Doped Graphene Quantum Dots for Cholesterol Sensing

et al. 2021

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“…We chose this condition for further studies. It should be noted that this is one of the best synthetic procedures so far reported for the direct formation of 25-HC from cholestanes or cholesterols [ 15 , 18 , 19 , 20 , 21 ]. As little as 2 moL% Ru(Bpga) catalyst gave the 25-HC derivatives in 46% yield, indicating the robustness of the catalyst under oxidative conditions.…”

Section: Resultsmentioning

confidence: 99%

Preparation of Oxysterols by C–H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst

et al. 2021

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Seven mono- and dihydroxycholesterols were prepared by direct C–H oxidation of the cholestane skeleton with a recently developed Ru(Bpga) catalyst (Ru(Bpga) = [RuCl (bpga) (PPh3)] Cl; bpga = 2-(bis(pyridin-2-ylmethyl)amino)-N-(2,6-dimethylphenyl)acetamide)). Due to the high selectivity of the Ru(Bpga) complex for tertiary C–H, the reaction afforded a mixture of 25-, 20-, 17-, and 14-oxygenated cholesterols that could be easily separated by high-performance liquid chromatography. These results suggest that late-stage C–H oxidation could be a viable strategy for preparing candidate metabolites of biologically important molecules.

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“…Several electrochemical methods were applied in the oxidation of cholesterol and derivatives affording, namely, allylic acetoxylation or hydroxylation products [95,96]. In effect, an electrochemical system for the aerobic oxidation of cholesteryl acetate induced by iron picolinate complexes was reported by Okamoto et al Interestingly, this procedure mainly afforded 7-hydroxylated products with high stereoselectivity (α:β ratio > 100:9), despite relatively low yields [97].…”

Section: Allylic Oxidationmentioning

confidence: 99%

“…Electrochemical methods were also developed and applied in the halogenation of steroids [96,[98][99][100], including Δ 5 -steroids, to afford 5α,6β-halogenated derivatives that have high biological interest and can be useful in the protection of the double bond in synthetic chemistry. In addition, these procedures can be valuable alternatives to the use of less green reagents namely chlorine gas.…”

Section: Other Oxidation Reactionsmentioning

confidence: 99%

Recent Highlights in Green Oxidative Chemical Processes Applied to Steroid Chemistry

Silvestre¹,

Silva²,

Salvador³

2016

Green Nanotechnology - Overview and Further Prospects

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Steroids and their oxidation products are widely distributed in living organisms and are important intermediates for the synthesis of many biologically active molecules. Due to their pharmacological and synthetic relevance, several oxidative chemical processes for the functionalization of the steroid nucleus have been developed. Green chemistry principles have been incorporated in some oxidative transformations of steroids, allowing significant advances in synthetic chemistry applied to these compounds. This chapter presents a selection of relevant applications of pharmaceutical green chemistry to steroid's oxidative processes. Special emphasis is given to catalytic processes encompassing heterogeneous nanocatalysts, whose application in this context is increasing over the past years. This chapter is organized according to the reaction type that includes alcohol oxidation, epoxidation of alkenes, and allylic oxidation of alkenes to enones, among other relevant oxidative transformations. Biocatalytic oxidative methods applied to steroid synthesis are not included in this review.

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Electrochemical oxidation of cholesterol

Cited by 31 publications

References 72 publications

Nanocomposite of CuInS/ZnS and Nitrogen-Doped Graphene Quantum Dots for Cholesterol Sensing

Nanocomposite of CuInS/ZnS and Nitrogen-Doped Graphene Quantum Dots for Cholesterol Sensing

Preparation of Oxysterols by C–H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst

Recent Highlights in Green Oxidative Chemical Processes Applied to Steroid Chemistry

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