A concise and stereoselective total synthesis of the clinically relevant tricyclic prostaglandin D2 metabolite (tricyclic-PGDM) methyl ester in racemic form was accomplished eight steps from a readily available known cyclopentene-diol derivative. The features nickel-catalyzed Ueno–Stork-type dicarbofunctionalization to generate two consecutive stereocenters, palladium-catalyzed carbonylative sp...

Aldehydes are electrophilic compounds to which humans are pervasively exposed. Despite a significant health risk due to exposure, the mechanisms of aldehyde toxicity are poorly understood. This ambiguity is likely due to the structural diversity of aldehyde derivatives and corresponding differences in chemical reactions and biological targets. To gain mechanistic insight, we have used parameter...

CDP-2,3-di-O-geranylgeranyl-sn-glycerol:L-serine O-archaetidyltransferase (archaetidylserine synthase) activity in cell extracts of Methanothermobacter thermautotrophicus cells was characterized. The enzyme catalyzed the formation of unsaturated archaetidylserine from CDP-unsaturated archaeol and L-serine. The identity of the reaction products was confirmed by thin-layer chromatography, fast at...

Ester compounds are widely used in applications such as solvents, plasticizers, polymers, lubricants, cosmetics, medicinals, agrochemicals, soaps and other surface active agents, to mention a few. In many of these applications the simultaneous knowledge of the phase behavior and interfacial properties is an advantage for designing better products and improved processes. The van der Waals densit...

Ozonolysis of methyl oleate monolayers at the air-water interface results in surprisingly rapid loss of material through cleavage of the C=C bond and evaporation/dissolution of reaction products. We determine using neutron reflectometry a rate coefficient of (5.7 ± 0.9) × 10(-10) cm(2) molecule(-1) s(-1) and an uptake coefficient of ∼3 × 10(-5) for the oxidation of a methyl ester monolayer: the...

In this study, an unexplored oil from the wodyetia bifurcata fruit was used for biodiesel production. The transesterification process implemented to convert raw into methyl ester (WBME) and influence of variables on WBME yield examined with response surface method (RSM) assisted Box-Behnken optimization. results RSM show that a maximum 94.67% achieved reaction time identified as influencing var...

Using protein kinase C partially purified from mouse brain cytosol, we examined the effect of a number of phorbol ester and nonphorbol tumor promoters on protein kinase C enzymatic activity and [3H]phorbol 12,13-dibutyrate binding. Mezerein and phorbol 12-retinoate 13-acetate, second stage tumor promoters, as well as the weak tumor promoter 4-O-methylphorbol 12-myristate 13-acetate stimulated k...

Ethanol causes pancreatic damage by an unknown mechanism. Previously, we demonstrated that a sustained rise of the cytosolic Ca(2+) concentration ([Ca(2+)](i)) causes pancreatic acinar cell injury. Here we have investigated the effects of ethanol and its metabolites on Ca(2+) signaling in pancreatic acinar cells. Most cells exposed to ethanol (up to 850 mM) showed little or no increase in [Ca(2...

Lovastatin has been shown to reduce cholesterol esterification in cholesterol-loaded human macrophages. Surprisingly, in nonloaded macrophages, lovastatin produces the opposite effect, lowering free cholesterol and increasing cholesteryl ester levels, as measured by high-performance liquid chromatography. In cholesterol-loaded cells, lovastatin reduced the cholesteryl esters of unsaturated but ...

The direct γ-carbon functionalization of α,β-unsaturated esters via N-Heterocyclic Carbene (NHC) catalysis is disclosed. This catalytically generated nucleophilic γ-carbon undergoes highly enantioselective additions to hydrazones. The resulting δ-lactam products can be readily transformed to optically enriched pipecolic acid derivatives.