Transfer Hydrogenation as a Redox Process in Nucleotides

Achrainer, Florian; Emel′yanenko, Vladimir N.; Tantawy, Waled A.; Verevkin, Sergey P.; Zipse, Hendrik

doi:10.1021/jp507855k

Cited by 11 publications

(13 citation statements)

References 18 publications

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“…Among four alcohols given in Table , ethylene glycol results in the formation of the smallest Pd nanoparticles, and MeOH forms the greatest nanoparticles. The hydrogenation enthalpies of the corresponding three aldehydes in the gas phase including methanal, ethanal, and 1‐propanal are −92.4, −69.1, and −61.27 kJ mol −1 , respectively. These values show that the oxidation rate of MeOH is lower than EtOH and PrOH.…”

Section: Resultsmentioning

confidence: 99%

Fabrication of High‐Performance Palladium Supported on Activated Charcoal Nanocatalyst for Synthesis of Morphine Opioid Analgesics

et al. 2020

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High-performance palladium supported on activated charcoal (Pd/AC H ) is an important nanocatalyst for the synthesis of different types of opioid analgesics. In this work, the Pd/AC H nanocatalysts are fabricated by a suitable method using the chemical reduction with ethylene glycol (EG), 1-propanol, ethanol, and methanol, which act as reducing, stabilizing, and dispersing agents. Since this method does not require surfactants and reducing agents that are hazardous to the environment and human health, it is an environmentally friendly method. The activity of produced nanocatalysts was determined by catalytic hydrogenation of 14-hydroxynormorphinone to noroxymorphone because noroxymorphone is the key active metabolite of oxycodone, noroxycodone, and oxymorphone. Among catalysts, it is specified that nanocatalyst prepared by EG (Pd/AC HEG ) has the highest activity. The effect of the EG for increasing the rate of Pd reduction is related to its high boiling point, which results in a decrease in particle size. The results of the reusability of the Pd/AC HEG nanocatalyst show that the activity of nanocatalyst is reduced by 12 % after four runs. Fourier-transform infrared (FTIR), inductively coupled plasma (ICP), transmission electron microscopy (TEM), x-ray diffraction (XRD), Brunauer-Emmett-Teller (BET), x-ray photoelectron spectroscopy (XPS), and H 2 chemisorption analyses were used for the analysis of Pd/AC H nanocatalysts.[a] Dr. Scheme 1. The CH reaction of 14-hydroxynormorphinone to noroxymorphone in presence Pd/AC catalyst ChemistrySelect Full Papers

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Section: Resultsmentioning

confidence: 99%

Fabrication of High‐Performance Palladium Supported on Activated Charcoal Nanocatalyst for Synthesis of Morphine Opioid Analgesics

et al. 2020

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“…We note at this point that hydrogenation energies ∆ hyd H obtained through combination of theoretically calculated reaction energies ∆ trh H for the transfer hydrogenation process (5) with the experimentally measured hydrogenation enthalpy of ethylene ∆ hyd H ( 2 ) = −136.3 ± 0.2 kJ/mol [23] are significantly more accurate than hydrogenation energies ∆ hyd H calculated for the direct reaction of H 2 with the respective alkenes [7].…”

Section: Resultsmentioning

confidence: 99%

“…Recent results obtained in a combined theoretical and experimental study to determine the heats of hydrogenation of the pyrimidine and purine bases indicate that the hydrogenation enthalpies of ketones and aldehydes derived from sugar models are, in part, closely similar to those of the pyrimidine bases [7]. The hydrogenation enthalpies are shown in Figure 1 such that a side-by-side comparison of all possible hydrogen transfer reactions is possible in a graphical way.…”

Section: Introductionmentioning

confidence: 99%

Transfer Hydrogenation in Open-Shell Nucleotides — A Theoretical Survey

Achrainer

Zipse

2014

Molecules

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Abstract:The potential of a larger number of sugar models to act as dihydrogen donors in transfer hydrogenation reactions has been quantified through the calculation of hydrogenation energies of the respective oxidized products. Comparison of the calculated energies to hydrogenation energies of nucleobases shows that many sugar fragment radicals can reduce pyrimidine bases such as uracil in a strongly exothermic fashion. The most potent reducing agent is the C3' ribosyl radical. The energetics of intramolecular transfer hydrogenation processes has also been calculated for a number of uridinyl radicals. The largest driving force for such a process is found for the uridin-C3'-yl radical, whose rearrangement to the C2'-oxidized derivative carrying a dihydrouracil is predicted to be exothermic by 61.1 kJ/mol in the gas phase.

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“…1 below) in microRNA mimics [5] regarding the binding kinetics of monoaquated Cisplatin, cis-[(NH 3 ) 2 PtCl(OH 2 )] + . The role of hydrogen transfer in redox processes involving nucleosides (i.e., the nucleobase and sugar residues) is yet another example [6]. Similarly, e.g., toll-like http://dx.doi.org/10.1016/j.ica.2016.02.048 0020-1693/Ó 2016 Elsevier B.V. All rights reserved.…”

Section: Introductionmentioning

confidence: 99%