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N-acyl or endocannnabanoid or NAPE

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https://www.readbyqxmd.com/read/28730809/ruthenium-catalyzed-1-6-aromatic-enamide-silylalkyne-cycloisomerization-approach-to-2-3-disubstituted-indoles
#1
Kohei Takamoto, Shohei Ohno, Norimichi Hyogo, Hiromichi Fujioka, Mitsuhiro Arisawa
Cycloisomerization is an atom economic procedure that converts dienes and enynes into cyclic molecules. To date, cycloisomerization between enamides and silylalkynes has not been explored. We found that N-acyl-N-vinyl-2-silylalkynylaniline derivatives undergo a cycloisomerization in the presence of a well-defined ruthenium hydride to give a 2,3-disubstitued indole. The vinyl and silylmethyl substituents on the 2- and 3-positions of the indole can be easily converted to other functional groups.
July 21, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28730283/blockade-of-alcohol-escalation-and-relapse-drinking-by-pharmacological-faah-inhibition-in-male-and-female-c57bl-6j-mice
#2
Yan Zhou, Benjamin I Schwartz, Joanna Giza, Steven S Gross, Francis S Lee, Mary Jeanne Kreek
BACKGROUND: Anandamide (AEA)-dependent signaling is regulated by the catabolic enzyme fatty acid amide hydrolase (FAAH). Several lines of evidence have demonstrated that FAAH and AEA are involved in the behavioral effects of alcohol. Therefore, we investigated whether a selective FAAH inhibitor, URB597 (cyclohexylcarbamic acid 3'-[aminocarbonyl]-[1,1'-biphenyl]-3-yl ester), altered alcohol intake in mice in a voluntary alcohol drinking model. METHODS: Mice, subjected to 3 weeks of chronic intermittent access (IA) in a two-bottle choice paradigm with 24-h access every other day, developed rapid escalation of alcohol intake and high preference...
July 20, 2017: Psychopharmacology
https://www.readbyqxmd.com/read/28726104/n-acyl-dopamines-induce-apoptosis-in-pc12-cell-line-via-the-gpr55-receptor-activation
#3
M G Akimov, A M Ashba, N M Gretskaya, V V Bezuglov
Dopamine amides of arachidonic, docosahexaenoic, and oleic acids were found to induce apoptosis in PC12 cells, which was blocked exclusively by antagonists and preincubation agonists of the receptor GPR55, belonging to the group of non-CB1/CB2 receptors.
May 2017: Doklady. Biochemistry and Biophysics
https://www.readbyqxmd.com/read/28720155/effect-of-slaughter-age-and-feeding-system-on-the-neutral-and-polar-lipid-composition-of-horse-meat
#4
X Belaunzaran, P Lavín, A R Mantecón, J K G Kramer, N Aldai
This study was undertaken to provide a thorough analysis of the neutral lipid (NL) and polar lipid (PL) fractions of horse meat that included the content and distribution of acyl and alkenyl moieties in foals under different rearing conditions. Two groups of crossbred horses were studied; the first group was selected from suckling foals produced under grazing conditions and slaughtered at 4 months of age (n=8), and the second group was selected from concentrate-finished foals and slaughtered at 12 months of age (n=7)...
July 19, 2017: Animal: An International Journal of Animal Bioscience
https://www.readbyqxmd.com/read/28715115/membrane-topology-and-identification-of-key-residues-of-eadact-a-plant-mboat-with-unusual-substrate-specificity
#5
Tam N T Tran, Jennifer Shelton, Susan Brown, Timothy P Durrett
Euonymus alatus diacylglycerol acetyltransferase (EaDAcT) catalyzes the transfer of an acetyl group from acetyl-CoA to the sn-3 position of diacylglycerol (DAG) to form 3-acetyl-1,2-diacyl-sn-glycerol (acetyl-TAG). EaDAcT belongs to a small, plant-specific subfamily of the membrane bound O-acyltransferases (MBOAT) that acylate different lipid substrates. Sucrose gradient density centrifugation revealed that EaDAcT colocalizes to the same fractions as an endoplasmic reticulum specific marker. By mapping the membrane topology of EaDAcT, we obtained an experimentally determined topology model for a plant MBOAT...
July 17, 2017: Plant Journal: for Cell and Molecular Biology
https://www.readbyqxmd.com/read/28714993/a-two-helix-motif-positions-the-lysophosphatidic-acid-acyltransferase-active-site-for-catalysis-within-the-membrane-bilayer
#6
Rosanna M Robertson, Jiangwei Yao, Stefan Gajewski, Gyanendra Kumar, Erik W Martin, Charles O Rock, Stephen W White
Phosphatidic acid (PA), the central intermediate in membrane phospholipid synthesis, is generated by two acyltransferases in a pathway conserved in all life forms. The second step in this pathway is catalyzed by 1-acyl-sn-glycerol-3-phosphate acyltransferase, called PlsC in bacteria. Here we present the crystal structure of PlsC from Thermotoga maritima, revealing an unusual hydrophobic/aromatic N-terminal two-helix motif linked to an acyltransferase αβ-domain that contains the catalytic HX4D motif. PlsC dictates the acyl chain composition of the 2-position of phospholipids, and the acyl chain selectivity 'ruler' is an appropriately placed and closed hydrophobic tunnel...
July 17, 2017: Nature Structural & Molecular Biology
https://www.readbyqxmd.com/read/28713595/fatty-acid-profiles-of-stipe-and-blade-from-the-norwegian-brown-macroalgae-laminaria-hyperborea-with-special-reference-to-acyl-glycerides-polar-lipids-and-free-fatty-acids
#7
Lena Foseid, Hanne Devle, Yngve Stenstrøm, Carl Fredrik Naess-Andresen, Dag Ekeberg
A thorough analysis of the fatty acid profiles of stipe and blade from the kelp species Laminaria hyperborea is presented. Lipid extracts were fractionated into neutral lipids, free fatty acids, and polar lipids, prior to derivatization and GC-MS analysis. A total of 42 fatty acids were identified and quantified, including the n-3 fatty acids α-linolenic acid, stearidonic acid, and eicosapentaenoic acid. The fatty acid amounts are higher in blade than in stipe (7.42 mg/g dry weight and 2.57 mg/g dry weight, resp...
2017: Journal of Lipids
https://www.readbyqxmd.com/read/28711408/biochemical-characteristics-of-newborns-with-carnitine-transporter-defect-identified-by-newborn-screening-in-california
#8
N M Gallant, K Leydiker, Y Wilnai, C Lee, F Lorey, L Feuchtbaum, H Tang, J Carter, G M Enns, S Packman, H J Lin, W R Wilcox, S D Cederbaum, J E Abdenur
Carnitine transporter defect (CTD; also known as systemic primary carnitine deficiency; MIM 212140) is due to mutations in the SLC22A5 gene and leads to extremely low carnitine levels in blood and tissues. Affected individuals may develop early onset cardiomyopathy, weakness, or encephalopathy, which may be serious or even fatal. The disorder can be suggested by newborn screening. However, markedly low newborn carnitine levels can also be caused by conditions unrelated to CTD, such as the low carnitine levels often associated with normal pregnancies and some metabolic disorders occurring in the mother...
July 8, 2017: Molecular Genetics and Metabolism
https://www.readbyqxmd.com/read/28708388/ni-catalyzed-alkene-carboacylation-via-amide-c-n-bond-activation
#9
James A Walker, Kevin L Vickerman, Jenna N Humke, Levi M Stanley
We report Ni-catalyzed formal carboacylation of o-allylbenzamides with arylboronic acid pinacol esters. The reaction is triggered by oxidative addition of an activated amide C-N bond to a Ni(0) catalyst and proceeds via alkene insertion into a Ni(II)-acyl bond. The exo-selective carboacylation reaction generates 2-benzyl-2,3-dihydro-1H-inden-1-ones in moderate to high yields (46-99%) from a variety of arylboronic acid pinacol esters and substituted o-allylbenzamides. These results show that amides are practical substrates for alkene carboacylation via amide C-N bond activation, and this approach bypasses challenges associated with alkene carboacylation triggered by C-C bond activation...
July 20, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28706006/integration-of-flux-measurements-to-resolve-changes-in-anabolic-and-catabolic-metabolism-in-cardiac-myocytes
#10
Andrew A Gibb, Pawel K Lorkiewicz, Yu-Ting Zheng, Xiang Zhang, Aruni Bhatnagar, Steven P Jones, Bradford G Hill
Although ancillary pathways of glucose metabolism are critical for synthesizing cellular building blocks and modulating stress responses, how they are regulated remains unclear.  In this study, we used radiometric glycolysis assays, [(13)C6]-glucose isotope tracing, and extracellular flux analysis to understand how phosphofructokinase (PFK)-mediated changes in glycolysis regulate glucose carbon partitioning into catabolic and anabolic pathways. Expression of kinase-deficient or phosphatase-deficient 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase in rat neonatal cardiomyocytes coordinately regulated glycolytic rate and lactate production...
July 13, 2017: Biochemical Journal
https://www.readbyqxmd.com/read/28703942/low-temperature-and-phosphate-deficiency-responsive-elements-control-dgtt3-expression-in-chlamydomonas-reinhardtii
#11
Xiaowen Fei, Ping Li, Xinghan Li, Xiaodong Deng
acyl-CoA:Diacylglycerol acyltransferases (DGAT) catalyse the final step of the triacylglycerol biosynthesis. Two major gene families have been shown to encode DGATs, DGAT1 and DGAT2. Abiotic factors such as low temperatures, nitrogen or phosphorus deficiency was reported to play important roles in the growth and development in green algae. Whether DGATs are induced by low temperatures or phosphorus deficiency, and the corresponding promoter elements are not reported yet. In this study, we found DGTT3 to have a significant response to low temperatures, phosphorus deficiency, and other stresses, such as high concentrations of NaCl, 20 μM GA, and 20 μM abscisic acid...
July 13, 2017: Journal of Eukaryotic Microbiology
https://www.readbyqxmd.com/read/28702662/chiral-squaramide-catalysed-enantioselective-michael-cyclization-cascade-reaction-of-3-hydroxyoxindoles-with-%C3%AE-%C3%AE-unsaturated-n-acylated-succinimides
#12
Sheng Ming, Bo-Liang Zhao, Da-Ming Du
A bifunctional squaramide-catalysed asymmetric Michael/cyclization cascade reaction of 3-hydroxyoxindoles with α,β-unsaturated N-acylated succinimides is disclosed. With quinine-derived squaramide as the catalyst, a broad range of the desired spirooxindole lactone derivatives bearing two contiguous stereocenters were obtained in good yields (up to 89%) with high diastereoselectivities (up to >95 : 5 dr) and excellent enantioselectivities (up to 99% ee).
July 12, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28702008/hypersensitive-response-of-plasmid-encoded-ahl-synthase-gene-to-lifestyle-and-nutrient-by-ensifer-adhaerens-x097
#13
Yanhua Zeng, Yanli Wang, Zhiliang Yu, Yili Huang
It is known that some bacteria, especially members of the family Rhizobiaceae, have multiple N-acyl homoserine lactones (AHL) synthase genes and produce multiple AHL signals. However, how bacteria selectively utilize these multiple genes and signals to cope with changing environments is poorly understood. Ensifer adhaerens is an important microorganism in terms of biotechnology, ecology and evolutionary. In this study, we investigated the AHL-based QS system of E. adhaerens X097 and its response to different lifestyles or nutrients...
2017: Frontiers in Microbiology
https://www.readbyqxmd.com/read/28698919/unperturbed-hydrocarbon-chains-and-liquid-phase-bilayer-lipid-chains-a-computer-simulation-study
#14
Alexander L Rabinovich, Alexander P Lyubartsev, Dmitrii V Zhurkin
In this work, the properties of saturated and unsaturated fatty acid acyl chains 16:0, 18:0, 18:1(n-9)cis, 18:2(n-6)cis, 18:3(n-3)cis, 18:4(n-3)cis, 18:5(n-3)cis, 20:4(n-6)cis, 20:5(n-3)cis and 22:6(n-3)cis in a bilayer liquid crystalline state and similar hydrocarbon chains (with CH[Formula: see text] terminal groups instead of C=O groups) in the unperturbed state characterised by a lack of long-range interaction were investigated. The unperturbed hydrocarbon chains were modelled by Monte Carlo simulations at temperature [Formula: see text] K; sixteen fully hydrated homogeneous liquid crystalline phosphatidylcholine bilayers containing these chains were studied by molecular dynamics simulations at the same temperature...
July 11, 2017: European Biophysics Journal: EBJ
https://www.readbyqxmd.com/read/28698362/structural-insights-into-lipoprotein-n-acylation-by-escherichia-coli-apolipoprotein-n-acyltransferase
#15
Cameron L Noland, Michele D Kattke, Jingyu Diao, Susan L Gloor, Homer Pantua, Mike Reichelt, Anand K Katakam, Donghong Yan, Jing Kang, Inna Zilberleyb, Min Xu, Sharookh B Kapadia, Jeremy M Murray
Gram-negative bacteria express a diverse array of lipoproteins that are essential for various aspects of cell growth and virulence, including nutrient uptake, signal transduction, adhesion, conjugation, sporulation, and outer membrane protein folding. Lipoprotein maturation requires the sequential activity of three enzymes that are embedded in the cytoplasmic membrane. First, phosphatidylglycerol:prolipoprotein diacylglyceryl transferase (Lgt) recognizes a conserved lipobox motif within the prolipoprotein signal sequence and catalyzes the addition of diacylglycerol to an invariant cysteine...
July 11, 2017: Proceedings of the National Academy of Sciences of the United States of America
https://www.readbyqxmd.com/read/28698248/ganglioside-glycosyltransferases-are-s-acylated-at-conserved-cysteine-residues-involved-in-homodimerization
#16
Sabrina Chumpen Ramirez, Fernando M Ruggiero, Jose Luis Daniotti, Javier Valdez Taubas
Ganglioside glycosyltransferases (GGTs) are type-II membrane proteins bearing a short N-terminal cytoplasmic tail, a transmembrane domain (TMD), and a lumenal catalytic domain. The expression and activity of these enzymes largely determine the quality of the glycolipids that decorate mammalian cells membranes. Many glycosyltransferases are themselves glycosylated and this is important for their proper localisation, but few if any other post-translational modifications of these proteins have been reported. Here we show that the GGTs, ST3Gal-V, ST8Sia-I, and β4GalNAcT-I are S-acylated at conserved cysteine residues located close the cytoplasmic border of their TMDs...
July 11, 2017: Biochemical Journal
https://www.readbyqxmd.com/read/28697551/n-acyl-homoserine-lactone-dynamics-during-biofilm-formation-of-a-1-2-4-trichlorobenzene-mineralizing-community-on-clay
#17
Hongjie Sheng, Mourad Harir, Lisa A Boughner, Xin Jiang, Philippe Schmitt-Kopplin, Reiner Schroll, Fang Wang
In Gram-negative bacteria, quorum sensing systems are based on the N-acyl-homoserine lactone (AHL) molecule. The objective of this study was to investigate the role of quorum sensing systems during biofilm formation by a microbial community while degrading the pollutant. Our model system included 1,2,4-trichlorobenzene (1,2,4-TCB) and its mineralizing Gram-negative bacterial community to investigate the relationships between AHL dynamics, cell growth and pollutant degradation. Biomineralization of 1,2,4-TCB was monitored for both the planktonic bacterial community with and without sterile clay particles in liquid cultures...
July 6, 2017: Science of the Total Environment
https://www.readbyqxmd.com/read/28695853/crystal-structure-of-the-n-terminal-domain-of-vqsr-from-pseudomonas-aeruginosa-at-2-1%C3%A2-%C3%A3-resolution
#18
Qing He, Kang Wang, Tiantian Su, Feng Wang, Lichuan Gu, Sujuan Xu
VqsR is a quorum-sensing (QS) transcriptional regulator which controls QS systems (las, rhl and pqs) by directly downregulating the expression of qscR in Pseudomonas aeruginosa. As a member of the LuxR family of proteins, VqsR shares the common motif of a helix-turn-helix (HTH)-type DNA-binding domain at the C-terminus, while the function of its N-terminal domain remains obscure. Here, the crystal structure of the N-terminal domain of VqsR (VqsR-N; residues 1-193) was determined at a resolution of 2.1 Å...
July 1, 2017: Acta Crystallographica. Section F, Structural Biology Communications
https://www.readbyqxmd.com/read/28694845/a-type-i-diacylglycerol-acyltransferase-modulates-triacylglycerol-biosynthesis-and-fatty-acid-composition-in-the-oleaginous-microalga-nannochloropsis-oceanica
#19
Hehong Wei, Ying Shi, Xiaonian Ma, Yufang Pan, Hanhua Hu, Yantao Li, Ming Luo, Henri Gerken, Jin Liu
BACKGROUND: Photosynthetic oleaginous microalgae are considered promising feedstocks for biofuels. The marine microalga, Nannochloropsis oceanica, has been attracting ever-increasing interest because of its fast growth, high triacylglycerol (TAG) content, and available genome sequence and genetic tools. Diacylglycerol acyltransferase (DGAT) catalyzes the last and committed step of TAG biosynthesis in the acyl-CoA-dependent pathway. Previous studies have identified 13 putative DGAT-encoding genes in the genome of N...
2017: Biotechnology for Biofuels
https://www.readbyqxmd.com/read/28690598/large-diversity-and-original-structures-of-acyl-homoserine-lactones-in-strain-mola-401-a-marine-rhodobacteraceae-bacterium
#20
Margot Doberva, Didier Stien, Jonathan Sorres, Nathalie Hue, Sophie Sanchez-Ferandin, Véronique Eparvier, Yoan Ferandin, Philippe Lebaron, Raphaël Lami
Quorum sensing (QS) is a density-dependent mechanism allowing bacteria to synchronize their physiological activities, mediated by a wide range of signaling molecules including N-acyl-homoserine lactones (AHLs). Production of AHL has been identified in various marine strains of Proteobacteria. However, the chemical diversity of these molecules still needs to be further explored. In this study, we examined the diversity of AHLs produced by strain MOLA 401, a marine Alphaproteobacterium that belongs to the ubiquitous Rhodobacteraceae family...
2017: Frontiers in Microbiology
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