Dataset Information

Glycerol as Precursor of Organoselanyl and Organotellanyl Alkynes.

ABSTRACT: Herein we describe the synthesis of organoselanyl and organotellanyl alkynes by the addition of lithium alkynylchalcogenolate (Se and Te) to tosyl solketal, easily obtained from glycerol. The alkynylchalcogenolate anions were generated in situ and added to tosyl solketal in short reaction times, furnishing in all cases the respective products of substitution in good yields. Some of the prepared compounds were deprotected using an acidic resin to afford new water-soluble 3-organotellanylpropane-1,2-diols. The synthetic versatility of the new chalcogenyl alkynes was demonstrated in the iodocyclization of 2,2-dimethyl-1,3-dioxolanylmethyl(2-methoxyphenylethynyl)selane 3f, which afforded 3-iodo-2-(2,2-dimethyl-1,3-dioxolanylmethyl) selenanylbenzo[b]furan in 85% yield, opening a new way to access water-soluble Se-functionalized benzo[b]furanes.

SUBMITTER: Lenardao EJ

PROVIDER: S-EPMC6155406 | biostudies-other | 2017 Mar

REPOSITORIES: biostudies-other

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Glycerol as Precursor of Organoselanyl and Organotellanyl Alkynes.

Lenardão Eder J EJ Borges Elton L EL Stach Guilherme G Soares Liane K LK Alves Diego D Schumacher Ricardo F RF Bagnoli Luana L Marini Francesca F Perin Gelson G

Molecules (Basel, Switzerland) 20170302 3

Herein we describe the synthesis of organoselanyl and organotellanyl alkynes by the addition of lithium alkynylchalcogenolate (Se and Te) to tosyl solketal, easily obtained from glycerol. The alkynylchalcogenolate anions were generated in situ and added to tosyl solketal in short reaction times, furnishing in all cases the respective products of substitution in good yields. Some of the prepared compounds were deprotected using an acidic resin to afford new water-soluble 3-organotellanylpropane-1 ...[more]

PMID: 28257120

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Project description:BackgroundGlycerol is a substrate for gluconeogenesis and fatty acid esterification in the liver, processes which are upregulated in obesity and may contribute to excess fat accumulation. Glycine and glutamate, in addition to cysteine, are components of glutathione, the major antioxidant in the liver. In principle, glycerol could be incorporated into glutathione via the TCA cycle or 3-phosphoglycerate, but it is unknown whether glycerol contributes to hepatic de novo glutathione biosynthesis.MethodsGlycerol metabolism to hepatic metabolic products including glutathione was examined in the liver from adolescents undergoing bariatric surgery. Participants received oral [U-13C3]glycerol (50 mg/kg) prior to surgery and liver tissue (0.2-0.7g) was obtained during surgery. Glutathione, amino acids, and other water-soluble metabolites were extracted from the liver tissue and isotopomers were quantified with nuclear magnetic resonance spectroscopy.ResultsData were collected from 8 participants (2 male, 6 female; age 17.1 years [range 14-19]; BMI 47.4 kg/m2 [range 41.3-63.3]). The concentrations of free glutamate, cysteine, and glycine were similar among participants, and so were the fractions of 13C-labeled glutamate and glycine derived from [U-13C3]glycerol. The signals from all component amino acids of glutathione - glutamate, cysteine and glycine - were strong and analyzed to obtain the relative concentrations of the antioxidant in the liver. The signals from glutathione containing [13C2]glycine or [13C2]glutamate derived from the [U-13C3]glycerol drink were readily detected, and 13C-labelling patterns in the moieties were consistent with the patterns in corresponding free amino acids from the de novo glutathione synthesis pathway. The newly synthesized glutathione with [U-13C3]glycerol trended to be lower in obese adolescents with liver pathology.ConclusionsThis is the first report of glycerol incorporation into glutathione through glycine or glutamate metabolism in human liver. This could represent a compensatory mechanism to increase glutathione in the setting of excess glycerol delivery to the liver.

Project description:Crude glycerol (CG) and glycerol pitch (GP) are highly alkaline residues from biodiesel and oleochemical plants, respectively, and have organic content which incurs high disposal cost and poses an environmental threat. Characterization of these residues for composition and properties could provide insight into their quality for proper disposal and can help the biodiesel industry to adopt more sustainable practices, such as reducing waste and improving the efficiency of the production process, hence minimizing the impact of the biodiesel supply chain to the environment. These data also allow the identification and exploration of new ways for their utilization and transformation into highly value-added products. In this study, we evaluated four CG samples (B, C, D, and E) and two GP samples (F and G) obtained from Malaysian palm oil refineries, and the results were compared with pure glycerol (A). Spectroscopic analysis was performed using FTIR, 1H-, and 13C-NMR. All samples had similar density to A (1.26 g/cm3), except for F (1.31 g/cm3), while the density for E and G could not be determined due to their physical states. The pH and viscosity largely varied in the range of 7.26–11.89 and 43–225 cSt, respectively. The glycerol content of CG (B, C, D, and E) was high and consistent (81.7–87.3%) whereas GP F and G had 71.5 and 63.9% glycerol content, respectively. Major contaminants in CG and GP were water and matter organic non-glycerol (MONG), respectively. The water, ash, soap, and salt content were considerably low, which varied from 3.4 to 14.1%, 3.9 to 13.0%, 0.1 to 5.7%, and 4.1 to 9.2% respectively. Thermal analysis of CG and GP exhibited four phases of decomposition attributed to the impurities compared to the single phase in A. All samples had calorific values lower than A (18.1 MJ/kg) between 9.0 and 17.7 MJ/kg. Based on the results, CG and GP have high glycerol content which reveals their potential to be used as feedstock in bioconversion and chemical or thermal treatment while impurities may be removed by pre-treatment if required. As palm oil is one of the main feedstocks for the oleochemical industry, this work underlines the importance of characterization of the residue generated to provide additional data and information on palm-based agricultural industry wastes, minimize the impact of palm oil supply chain on the environment, and explore its potential usage for value-addition. Supplementary Information The online version contains supplementary material available at 10.1007/s13399-023-04003-4.

Dataset Information

Glycerol as Precursor of Organoselanyl and Organotellanyl Alkynes.

Publications

Glycerol as Precursor of Organoselanyl and Organotellanyl Alkynes.

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