Browse
Submit Data
Databases
API
Help

Dataset Information

29 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Separation of Saturated Fatty Acids and Fatty Acid Methyl Esters with Epoxy Nanofiltration Membranes.

ABSTRACT: Epoxy nanofiltration membranes were fabricated by the step polymerization of a primary diamine and a diepoxide or triepoxide conomomer. Membrane selectivity and flux were tuned by changing the identity of the diepoxides and by increasing the concentration of triepoxides in the polymerization. The membranes were used to separate even chain length saturated fatty acids (FAs) and saturated fatty acid methyl esters (FAMEs) that possessed molecular weights between 80 - 300 g mol-1. Our membranes show excellent selectivities of up to 100:1 for the separation of the C4-C18 FAMEs. The flux of the FAMEs through the membranes showed an exponential dependence based on the number of carbons. Fabrication of thin epoxy membranes with thicknesses of 150 nm allowed for an increase in flux of FAMEs through the membrane and demonstrated that these separations can be used under industrially relevant conditions.

SUBMITTER: Gilmer CM

PROVIDER: S-EPMC5858744 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Separation of Saturated Fatty Acids and Fatty Acid Methyl Esters with Epoxy Nanofiltration Membranes.

Gilmer Chad M CM Zvokel Christina C Vick Alexandra A Bowden Ned B NB

RSC advances 20171208

Epoxy nanofiltration membranes were fabricated by the step polymerization of a primary diamine and a diepoxide or triepoxide conomomer. Membrane selectivity and flux were tuned by changing the identity of the diepoxides and by increasing the concentration of triepoxides in the polymerization. The membranes were used to separate even chain length saturated fatty acids (FAs) and saturated fatty acid methyl esters (FAMEs) that possessed molecular weights between 80 - 300 g mol<sup>-1</sup>. Our mem ...[more]

PMID: 29568507

Similar Datasets

Reactive Epoxy Nanofiltration Membranes with Disulfide Bonds for the Separation of Multicomponent Chemical Mixtures.

Project description:This article reports the fabrication of organic solvent nanofiltration membranes containing a labile disulfide bond, which is broken by reaction with a chemical stimulus. These membranes are a new generation of smart membranes that have tailored selectivities and flux that can be altered by reacting with a chemical stimulus. The selectivity and flux of chemicals through the membranes was controlled by varying the concentration of disulfide bonds in the membrane. When the disulfide bonds were cleaved, the pores in the membrane became larger and yielded different separation properties. The membrane selectivity was changed by up to 70% and flux was increased up to 5×. The rapid change in selectivity of the membrane allowed for the separation of three-component mixtures. A three-component mixture of 33.3% m-dinitrobenzene, 33.3% triphenylmethane, and 33.3% 1,3,5-tris(diphenylamino)benzene (TDAB) was separated into three different fractions that were significantly enriched in one of the three molecules. The first fraction contained m-dinitrobenzene at 82% purity and 84% yield, the second fraction contained triphenylmethane at 67% purity and 49% yield, and the third fraction contained TDAB at 71% purity and 88% yield.

| S-EPMC6120735 | biostudies-literature

Structural characterization of saturated branched chain fatty acid methyl esters by collisional dissociation of molecular ions generated by electron ionization.

Project description:Saturated branched chain fatty acids (BCFA) are present as complex mixtures in numerous biological samples. The traditional method for structure elucidation, electron ionization (EI) mass spectrometry, sometimes does not unambiguously enable assignment of branching in isomeric BCFA. Zirrolli and Murphy (Zirrolli , J. A. , and R. A. Murphy. 1993. Low-energy tandem mass spectrometry of the molecular ion derived from fatty acid methyl esters: a novel method for analysis of branched-chain fatty acids. J. Am. Soc. Mass Spectrom. 4: 223-229.) showed that the molecular ions of four BCFA methyl ester (BCFAME) yield highly characteristic fragments upon collisional dissociation using a triple quadrupole instrument. Here, we confirm and extend these results by analysis using a tabletop 3-D ion trap for activated molecular ion EI-MS/MS to 30 BCFAME. iso-BCFAME produces a prominent ion (30-100% of base peak) for [M-43] (M-C₃H₇), corresponding to the terminal isopropyl moiety in the original iso-BCFAME. Anteiso-FAME yield prominent ions (20-100% of base peak) corresponding to losses on both side of the methyl branch, [M-29] and [M-57], and tend to produce more prominent m/z 115 peaks corresponding to a cyclization product around the ester. Dimethyl and tetramethyl FAME, with branches separated by at least one methylene group, yield fragment on both sides of the sites of methyl branches that are more than 6 C away from the carboxyl carbon. EI-MS/MS yields uniquely specific ions that enable highly confident structural identification and quantification of BCFAME.

| S-EPMC3243476 | biostudies-literature

Saturated fatty acids regulate retinoic acid signaling and suppress tumorigenesis by targeting fatty acid-binding protein 5

Project description:Long chain fatty acids (LCFA) serve as energy sources, components of cell membranes, and precursors for signalling molecules. Here we show that these important biological compounds also regulate gene expression by controlling the transcriptional activities of the retinoic acid (RA)-activated nuclear receptors RAR and PPARβ/δ. Our data indicates that these activities of LCFA are mediated by FABP5, a protein that delivers ligands from the cytosol to nuclear PPARβ/δ. Both saturated and unsaturated LCFA (SLCFA, ULCFA) tightly bind to FABP5, thereby displacing RA and diverting it to RAR. However, while SLCFA inhibit, ULCFA activate the FABP5/PPARβ/δ pathway. By concomitantly promoting the activation of RAR and inhibiting the activity of PPARβ/δ, SLCFA suppress the growth and oncogenic properties of FABP5-expressing carcinoma cells both in cultured cells and in vivo.

2015-09-25 | GSE73186 | GEO

Saturated phosphatidic acids mediate saturated fatty acid-induced vascular calcification and lipotoxicity.

Project description:Recent evidence indicates that saturated fatty acid-induced (SFA-induced) lipotoxicity contributes to the pathogenesis of cardiovascular and metabolic diseases; however, the molecular mechanisms that underlie SFA-induced lipotoxicity remain unclear. Here, we have shown that repression of stearoyl-CoA desaturase (SCD) enzymes, which regulate the intracellular balance of SFAs and unsaturated FAs, and the subsequent accumulation of SFAs in vascular smooth muscle cells (VSMCs), are characteristic events in the development of vascular calcification. We evaluated whether SMC-specific inhibition of SCD and the resulting SFA accumulation plays a causative role in the pathogenesis of vascular calcification and generated mice with SMC-specific deletion of both Scd1 and Scd2. Mice lacking both SCD1 and SCD2 in SMCs displayed severe vascular calcification with increased ER stress. Moreover, we employed shRNA library screening and radiolabeling approaches, as well as in vitro and in vivo lipidomic analysis, and determined that fully saturated phosphatidic acids such as 1,2-distearoyl-PA (18:0/18:0-PA) mediate SFA-induced lipotoxicity and vascular calcification. Together, these results identify a key lipogenic pathway in SMCs that mediates vascular calcification.

| S-EPMC4665795 | biostudies-other

Heterologous production of polycyclopropanated fatty acids and their methyl esters in Streptomyces.

Project description:Polycyclopropanated (POP) compounds show promise as fuels as their energy density can be greater than jet and rocket fuels in current use, but realizing their full potential requires significant development. This protocol guides the production of polycyclopropanated fatty acids in Streptomyces; POP production in another host remains to be demonstrated. This method can serve as a baseline for further development of POP as well as other polyketide products. For complete details on the use and execution of this protocol, please refer to Cruz-Morales et al. (2022).1.

| S-EPMC10064271 | biostudies-literature

Preparation of fatty acid methyl esters for gas-liquid chromatography.

Project description:A convenient method using commercial aqueous concentrated HCl (conc. HCl; 35%, w/w) as an acid catalyst was developed for preparation of fatty acid methyl esters (FAMEs) from sterol esters, triacylglycerols, phospholipids, and FFAs for gas-liquid chromatography (GC). An 8% (w/v) solution of HCl in methanol/water (85:15, v/v) was prepared by diluting 9.7 ml of conc. HCl with 41.5 ml of methanol. Toluene (0.2 ml), methanol (1.5 ml), and the 8% HCl solution (0.3 ml) were added sequentially to the lipid sample. The final HCl concentration was 1.2% (w/v). This solution (2 ml) was incubated at 45 degrees C overnight or heated at 100 degrees C for 1-1.5 h. The amount of FFA formed in the presence of water derived from conc. HCl was estimated to be <1.4%. The yields of FAMEs were >96% for the above lipid classes and were the same as or better than those obtained by saponification/methylation or by acid-catalyzed methanolysis/methylation using commercial anhydrous HCl/methanol. The method developed here could be successfully applied to fatty acid analysis of various lipid samples, including fish oils, vegetable oils, and blood lipids by GC.

| S-EPMC2817593 | biostudies-literature

Novel fatty acid methyl esters from the actinomycete Micromonospora aurantiaca.

Project description:The volatiles released by Micromonospora aurantiaca were collected by means of a closed-loop stripping apparatus (CLSA) and analysed by GC-MS. The headspace extracts contained more than 90 compounds from different classes. Fatty acid methyl esters (FAMEs) comprised the major compound class including saturated unbranched, monomethyl and dimethyl branched FAMEs in diverse structural variants: Unbranched, α-branched, γ-branched, (ω-1)-branched, (ω-2)-branched, α- and (ω-1)-branched, γ- and (ω-1)-branched, γ- and (ω-2)-branched, and γ- and (ω-3)-branched FAMEs. FAMEs of the last three types have not been described from natural sources before. The structures for all FAMEs have been suggested based on their mass spectra and on a retention index increment system and verified by the synthesis of key reference compounds. In addition, the structures of two FAMEs, methyl 4,8-dimethyldodecanoate and the ethyl-branched compound methyl 8-ethyl-4-methyldodecanoate were deduced from their mass spectra. Feeding experiments with isotopically labelled [(2)H(10)]leucine, [(2)H(10)]isoleucine, [(2)H(8)]valine, [(2)H(5)]sodium propionate, and [methyl-(2)H(3)]methionine demonstrated that the responsible fatty acid synthase (FAS) can use different branched and unbranched starter units and is able to incorporate methylmalonyl-CoA elongation units for internal methyl branches in various chain positions, while the methyl ester function is derived from S-adenosyl methionine (SAM).

| S-EPMC3252875 | biostudies-literature

ATGL is a biosynthetic enzyme for fatty acid esters of hydroxy fatty acids.

Project description:Branched fatty acid (FA) esters of hydroxy FAs (HFAs; FAHFAs) are recently discovered lipids that are conserved from yeast to mammals1,2. A subfamily, palmitic acid esters of hydroxy stearic acids (PAHSAs), are anti-inflammatory and anti-diabetic1,3. Humans and mice with insulin resistance have lower PAHSA levels in subcutaneous adipose tissue and serum1. PAHSA administration improves glucose tolerance and insulin sensitivity and reduces inflammation in obesity, diabetes and immune-mediated diseases1,4-7. The enzyme(s) responsible for FAHFA biosynthesis in vivo remains unknown. Here we identified adipose triglyceride lipase (ATGL, also known as patatin-like phospholipase domain containing 2 (PNPLA2)) as a candidate biosynthetic enzyme for FAHFAs using chemical biology and proteomics. We discovered that recombinant ATGL uses a transacylation reaction that esterifies an HFA with a FA from triglyceride (TG) or diglyceride to produce FAHFAs. Overexpression of wild-type, but not catalytically dead, ATGL increases FAHFA biosynthesis. Chemical inhibition of ATGL or genetic deletion of Atgl inhibits FAHFA biosynthesis and reduces the levels of FAHFA and FAHFA-TG. Levels of endogenous and nascent FAHFAs and FAHFA-TGs are 80-90 per cent lower in adipose tissue of mice in which Atgl is knocked out specifically in the adipose tissue. Increasing TG levels by upregulating diacylglycerol acyltransferase (DGAT) activity promotes FAHFA biosynthesis, and decreasing DGAT activity inhibits it, reinforcing TGs as FAHFA precursors. ATGL biosynthetic transacylase activity is present in human adipose tissue underscoring its potential clinical relevance. In summary, we discovered the first, to our knowledge, biosynthetic enzyme that catalyses the formation of the FAHFA ester bond in mammals. Whereas ATGL lipase activity is well known, our data establish a paradigm shift demonstrating that ATGL transacylase activity is biologically important.

| S-EPMC9242854 | biostudies-literature

Saturated fatty acids regulate retinoic acid signalling and suppress tumorigenesis by targeting fatty acid-binding protein 5.

Project description:Long chain fatty acids (LCFA) serve as energy sources, components of cell membranes and precursors for signalling molecules. Here we show that these biological compounds also regulate gene expression and that they do so by controlling the transcriptional activities of the retinoic acid (RA)-activated nuclear receptors RAR and PPAR?/?. The data indicate that these activities of LCFA are mediated by FABP5, which delivers ligands from the cytosol to nuclear PPAR?/?. Both saturated and unsaturated LCFA (SLCFA, ULCFA) bind to FABP5, thereby displacing RA and diverting it to RAR. However, while SLCFA inhibit, ULCFA activate the FABP5/PPAR?/? pathway. We show further that, by concomitantly promoting the activation of RAR and inhibiting the activation of PPAR?/?, SLCFA suppress the oncogenic properties of FABP5-expressing carcinoma cells in cultured cells and in vivo. The observations suggest that compounds that inhibit FABP5 may constitute a new class of drugs for therapy of certain types of cancer.

| S-EPMC4662070 | biostudies-literature

Hemodialysis and erythrocyte epoxy fatty acids.

Project description:Fatty acid products derived from cytochromes P450 (CYP) monooxygenase and lipoxygenase (LOX)/CYP ω/(ω-1)-hydroxylase pathways are a superclass of lipid mediators with potent bioactivities. Whether or not the chronic kidney disease (CKD) and hemodialysis treatments performed on end-stage renal disease (ESRD) patients affect RBC epoxy fatty acids profiles remains unknown. Measuring the products solely in plasma is suboptimal. Since such determinations invariably ignore red blood cells (RBCs) that make up 3 kg of the circulating blood. RBCs are potential reservoirs for epoxy fatty acids that regulate cardiovascular function. We studied 15 healthy persons and 15 ESRD patients undergoing regular hemodialysis treatments. We measured epoxides derived from CYP monooxygenase and metabolites derived from LOX/CYP ω/(ω-1)-hydroxylase pathways in RBCs by LC-MS/MS tandem mass spectrometry. Our data demonstrate that various CYP epoxides and LOX/CYP ω/(ω-1)-hydroxylase products are increased in RBCs of ESRD patients, compared to control subjects, including dihydroxyeicosatrienoic acids (DHETs), epoxyeicosatetraenoic acids (EEQs), dihydroxydocosapentaenoic acids (DiHDPAs), and hydroxyeicosatetraenoic acids (HETEs). Hemodialysis treatment did not affect the majority of those metabolites. Nevertheless, we detected more pronounced changes in free metabolite levels in RBCs after dialysis, as compared with the total RBC compartment. These findings indicate that free RBC eicosanoids should be considered more dynamic or vulnerable in CKD.

| S-EPMC7592498 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data