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Reactivity of (Vicinal) Carbonyl Compounds with Urea.

ABSTRACT: Urea removal from dialysate is the major obstacle in realization of a miniature dialysis device, based on continuous dialysate regeneration in a closed loop, used for the treatment of patients suffering from end-stage kidney disease. For the development of a polymeric urea sorbent, capable of removing urea from dialysate with high binding capacities and fast reaction kinetics, a systematic kinetic study was performed on the reactivity of urea with a library of low-molecular-weight carbonyl compounds in phosphate-buffered saline (pH 7.4) at 323 K. It was found that dialdehydes do not react with urea under these conditions but need to be activated under acidic conditions and require aldehyde groups in close proximity to each other to allow a reaction with urea. Among the 31 (hydrated) carbonyl compounds tested, triformylmethane, ninhydrin, and phenylglyoxaldehyde were the most reactive ones with urea. This is attributed to the low dehydration energies of these compounds, as calculated by Gibbs free energy differences between the hydrated and dehydrated carbonyl compounds, which are favorable for the reaction with urea. Therefore, future urea sorbents should contain such functional groups at the highest possible density.

SUBMITTER: Jong JAW

PROVIDER: S-EPMC6681983 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Electrochemically driven desaturation of carbonyl compounds.

Project description:Electrochemical techniques have long been heralded for their innate sustainability as efficient methods to achieve redox reactions. Carbonyl desaturation, as a fundamental organic oxidation, is an oft-employed transformation to unlock adjacent reactivity through the formal removal of two hydrogen atoms. To date, the most reliable methods to achieve this seemingly trivial reaction rely on transition metals (Pd or Cu) or stoichiometric reagents based on I, Br, Se or S. Here we report an operationally simple pathway to access such structures from enol silanes and phosphates using electrons as the primary reagent. This electrochemically driven desaturation exhibits a broad scope across an array of carbonyl derivatives, is easily scalable (1-100 g) and can be predictably implemented into synthetic pathways using experimentally or computationally derived NMR shifts. Systematic comparisons to state-of-the-art techniques reveal that this method can uniquely desaturate a wide array of carbonyl groups. Mechanistic interrogation suggests a radical-based reaction pathway.

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Carbonyl compounds in the gas phase are critical determinants of wood smoke toxicity

Project description:Epidemiological studies identified air pollution as one of the prime causes for human morbidity and mortality due to harmful effects mainly on the cardiovascular and respiratory system. Damage to the lung leads to several severe diseases such as fibrosis, chronic obstructive pulmonary disease and cancer. Noxious environmental aerosols are comprised of a gas and particulate phase representing highly complex chemical mixtures composed of myriads of compounds. Although some critical pollutants, foremost particulate matter (PM), could be linked to adverse health effects, a comprehensive understanding of relevant biological mechanisms and detrimental aerosol constituents is still lacking. Here, we employed a systems toxicology approach focusing on wood combustion, an important source for air pollution, and demonstrate a key role of the gas phase, specifically carbonyls, to drive adverse effects. Transcriptional profiling and biochemical analysis of human lung cells exposed at the air-liquid-interface determined the DNA damage and stress response as well as perturbation of cellular metabolism as major key events. Connectivity mapping revealed a high similarity of gene expression signatures induced by wood smoke and agents prompting DNA-protein crosslinks (DPCs). Indeed, various gaseous aldehydes were detected in wood smoke, which promote DPCs, initiate similar genomic responses and are responsible for DNA damage provoked by wood smoke. Hence, systems toxicology enables the discovery of critical constituents of complex mixtures i.e. aerosols and highlights the role of carbonyls on top of particulate matter as important health hazard.

2023-09-01 | GSE228624 | GEO

Direct nucleophilic trifluoromethylation of carbonyl compounds by potent greenhouse gas, fluoroform: Improving the reactivity of anionoid trifluoromethyl species in glymes.

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Carbonyl Compounds in Mainstream Smoke of Hemp Cigarettes.

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Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds.

Project description:A nickel-catalyzed conjunctive cross-coupling of non-conjugated alkenes, alkyl halides, and alkylzinc reagents is reported. Regioselectivity is controlled by chelation of a removable bidentate 8-aminoquinoline directing group. Under optimized conditions, a wide range of 1,2-dialkylated products can be accessed in moderate to excellent yields. To the best of our knowledge, this report represents the first example of three-component 1,2-dialkylation of non-conjugated alkenes to introduce differentiated alkyl fragments.

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Directed, nickel-catalyzed 1,2-alkylsulfenylation of alkenyl carbonyl compounds.

Project description:We report a regioselective, nickel-catalyzed syn-1,2-carbosulfenylation of non-conjugated alkenyl carbonyl compounds with alkyl/arylzinc nucleophiles and tailored N-S electrophiles. This method allows the simultaneous installation of a variety of C(sp3) and S(Ar) (or Se(Ar)) groups onto unactivated alkenes, which complements previously developed 1,2-carbosulfenylation methodology in which only C(sp2) nucleophiles are compatible. A bidentate directing auxiliary controls regioselectivity, promotes high syn-stereoselectivity with a variety of E- and Z-internal alkenes, and enables the use of an array of electrophilic sulfenyl (and seleno) electrophiles. Among compatible electrophiles, those with N-alkyl-benzamide leaving groups were found to be especially effective, as determined through comprehensive structure-reactivity mapping.

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Reactivity of a Ruthenium-Carbonyl Complex in the Methanol Dehydrogenation Reaction.

Project description:Finding new catalysts for the release of molecular hydrogen from methanol is of high relevance in the context of the development of sustainable energy carriers. Herein, we report that the ruthenium complex Ru(salbinapht)(CO)(Pi-Pr3) {salbinapht=2-[({2'-[(2-hydroxybenzyl)amino]-[1,1'-binaphthalen]-2-yl}imino)methyl]phenolato} (2) catalyzes the methanol dehydrogenation reaction in the presence of base and water to yield H2, formate, and carbonate. Dihydrogen is the only gas detected and a turnover frequency up to 55?h-1 at 82?°C is reached. Complex 2 bears a carbonyl ligand that is derived from methanol, as is demonstrated by labeling experiments. The carbonyl ligand can be treated with base to form formate (HCOO-) and hydrogen. The nature of the active species is further shown not to contain a CO ligand but likely still possesses a salen-derived ligand. During catalysis, formation of Ru(CO)2(H)2(P-iPr3)2 is occasionally observed, which is also an active methanol dehydrogenation catalyst.

| S-EPMC5129501 | biostudies-literature

Dynamic thiol exchange with ?-sulfido-?,?-unsaturated carbonyl compounds and dithianes.

Project description:A reversible covalent bond exchange of thiols, ?-sulfido-?,?-unsaturated carbonyls, and dithianes has been studied in DMSO and D(2)O/DMSO mixtures. The equilibrium between thiols and ?-sulfido-?,?-unsaturated carbonyls is obtained within a few hours, while the equilibration starting with the ?-dithiane carbonyls and thiols requires a few days. This time scale makes the system ideal for utilization in dynamic combinatorial chemistry.

| S-EPMC3472802 | biostudies-literature

Reactive carbonyl compounds (RCCs) cause aggregation and dysfunction of fibrinogen.

Project description:Fibrinogen is a key protein involved in coagulation and its deposition on blood vessel walls plays an important role in the pathology of atherosclerosis. Although the causes of fibrinogen (fibrin) deposition have been studied in depth, little is known about the relationship between fibrinogen deposition and reactive carbonyl compounds (RCCs), compounds which are produced and released into the blood and react with plasma protein especially under conditions of oxidative stress and inflammation. Here, we investigated the effect of glycolaldehyde on the activity and deposition of fibrinogen compared with the common RCCs acrolein, methylglyoxal, glyoxal and malondialdehyde. At the same concentration (1 mmol/L), glycolaldehyde and acrolein had a stronger suppressive effect on fibrinogen activation than the other three RCCs. Fibrinogen aggregated when it was respectively incubated with glycolaldehyde and the other RCCs, as demonstrated by SDS-PAGE, electron microscopy and intrinsic fluorescence intensity measurements. Staining with Congo Red showed that glycolaldehyde- and acrolein-fibrinogen distinctly formed amyloid-like aggregations. Furthermore, the five RCCs, particularly glycolaldehyde and acrolein, delayed human plasma coagulation. Only glycolaldehyde showed a markedly suppressive effect on fibrinogenesis, none did the other four RCCs when their physiological blood concentrations were employyed, respectively. Taken together, it is glycolaldehyde that suppresses fibrinogenesis and induces protein aggregation most effectively, suggesting a putative pathological process for fibrinogen (fibrin) deposition in the blood.

| S-EPMC4875355 | biostudies-literature

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