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N-acyl or endocannnabanoid or NAPE

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https://www.readbyqxmd.com/read/28535043/identification-and-quantification-of-acylated-homoserine-lactones-in-shewanella-baltica-the-specific-spoilage-organism-of-pseudosciaena-crocea-by-ultra-high-performance-liquid-chromatography-coupled-to-triple-quadrupole-mass-spectrometry
#1
Yanbo Wang, Xiaoxiao Zhang, Chong Wang, Linglin Fu, Yanyao Yi, Yan Zhang
Bacteria communicate with one another using chemical signal molecules called autoinducers, and the most prevalent autoinducers used by Gram-negative bacteria are N-acylated homoserine lactones (AHLs). However, AHLs are hardly detected in Shewanella baltica, the specific spoilage organism of Pseudosciaena crocea. In this study, we applied ultra-high-performance liquid chromatography coupled to triple quadrupole tandem mass spectrometry (UHPLC-QqQ-MS/MS) to determine AHLs. This method enabled the quantification of up to 11 AHLs within 5...
May 23, 2017: Journal of Agricultural and Food Chemistry
https://www.readbyqxmd.com/read/28530397/synthesis-of-1-4-oxazepane-2-5-diones-via-cyclization-of-rotationally-restricted-amino-acid-precursors-and-structural-reassignment-of-serratin
#2
Ewout Ruysbergh, Kristof Van Hecke, Christian Victor Stevens, Norbert De Kimpe, Sven Mangelinckx
Several natural products containing a 1,4-oxazepane-2,5-dione-core are known. One example is serratin, isolated from Serratia marcescens. Due to the presence of a carboxylic amide, which has a preference for a trans-conformation, and the presence of a labile lactone in this core, many synthetic methodologies commonly used for the cyclization towards medium-sized heterocycles cannot be applied. As N-acyl amino acids without a third substituent at nitrogen failed to undergo ring-closure, several N-protecting groups were evaluated...
May 22, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28530166/quorum-sensing-and-rsam-regulons-of-the-rice-pathogen-pseudomonas-fuscovaginae
#3
Gordana Uzelac, Hitendra Kumar Patel, Giulia Devescovi, Danilo Licastro, Vittorio Venturi
Pseudomonas fuscovaginae (Pfv) is an emerging plant pathogen causing sheath brown rot in rice, as well as diseases in other gramineae food crops including maize, sorghum and wheat. Pfv possesses two conserved N-acyl homoserine lactone (AHL) quorum sensing (QS) systems called PfvI/R and PfsI/R, which are repressed by RsaL and RsaM, respectively. The two systems are not hierarchically organized and are involved in plant virulence. In this study the AHL QS PfsI/R, PfvI/R and RsaM regulons were determined by transcriptomic analysis...
May 22, 2017: Microbiology
https://www.readbyqxmd.com/read/28526845/chemical-structure-of-the-lipid-a-component-of-pseudomonas-sp-strain-pamc-28618-from-thawing-permafrost-in-relation-to-pathogenicity
#4
Han-Gyu Park, Ganesan Sathiyanarayanan, Cheol-Hwan Hwang, Da-Hee Ann, Jung-Ho Kim, Geul Bang, Kyoung-Soon Jang, Hee Wook Ryu, Yoo Kyung Lee, Yung-Hun Yang, Yun-Gon Kim
Climate change causes permafrost thawing, and we are confronted with the unpredictable risk of newly discovered permafrost microbes that have disease-causing capabilities. Here, we first characterized the detailed chemical structure of the lipid A moiety from a Pseudomonas species that was isolated from thawing arctic permafrost using MALDI-based mass spectrometric approaches (i.e., MALDI-TOF MS and MALDI-QIT-TOF MS(n)). The MALDI multi-stage mass spectrometry (MS) analysis of lipid A extracted from the Pseudomonas sp...
May 19, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28526351/docosahexaenoyl-serotonin-emerges-as-most-potent-inhibitor-of-il-17-and-ccl-20-released-by-blood-mononuclear-cells-from-a-series-of-n-acyl-serotonins-identified-in-human-intestinal-tissue
#5
Ya Wang, Michiel G J Balvers, Henk F J Hendriks, Tessa Wilpshaar, Tjarda van Heek, Renger F Witkamp, Jocelijn Meijerink
Fatty acid amides (FAAs), conjugates of fatty acids with ethanolamine, mono-amine neurotransmitters or amino acids are a class of molecules that display diverse functional roles in different cells and tissues. Recently we reported that one of the serotonin-fatty acid conjugates, docosahexaenoyl serotonin (DHA-5-HT), previously found in gut tissue of mouse and pig, attenuates the IL-23-IL-17 signaling axis in LPS-stimulated mice macrophages. However, its presence and effects in humans remained to be elucidated...
May 16, 2017: Biochimica et Biophysica Acta
https://www.readbyqxmd.com/read/28525716/diastereoselective-and-catalytic-%C3%AE-alkylation-of-chiral-n-acyl-thiazolidinethiones-with-stable-carbocationic-salts
#6
Stuart C D Kennington, Mònica Ferré, Juan M Romo, Pedro Romea, Fèlix Urpí, Mercè Font-Bardia
Direct nickel-catalyzed alkylation of chiral (N)-acyl-4-isopropyl-1,3-thiazolidine-2- thiones using a commercially available nickel(II) complex, (Me3P)2NiCl2, has been developed for tropylium and trityl tetrafluoroborate salts. The reaction provides a single diastereomer of the corresponding adducts in good to high yields, which, in turn, can be easily converted into a wide array of enantiomerically pure compounds that are difficult to obtain by other asymmetric procedures.
May 19, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28522606/structural-analysis-of-the-dual-function-thioesterase-sav606-unravels-the-mechanism-of-michael-addition-of-glycine-to-an-%C3%AE-%C3%AE-unsaturated-thioester
#7
Taichi Chisuga, Akimasa Miyanaga, Fumitaka Kudo, Tadashi Eguchi
Thioesterases catalyze hydrolysis of acyl thioesters to release carboxylic acid or macrocyclization to produce the corresponding macrocycle in the biosynthesis of fatty acids, polyketides, or nonribosomal peptides. Recently, we reported that the thioesterase CmiS1 from Streptomyces sp. MJ635-86F5 catalyzes the Michael addition of glycine to an α,β-unsaturated fatty acyl thioester followed by thioester hydrolysis in the biosynthesis of the macrolactam antibiotic cremimycin. However, the molecular mechanisms of CmiS1-catalyzed reactions are unclear...
May 18, 2017: Journal of Biological Chemistry
https://www.readbyqxmd.com/read/28518069/modification-and-functionalization-of-the-guanidine-group-by-tailor-made-precursors
#8
Tobias G Kapp, Maximilian Fottner, Horst Kessler
The guanidine group is one of the most important pharmacophoric groups in medicinal chemistry. The only amino acid carrying a guanidine group is arginine. In this article, an easy method for the modification of the guanidine group in peptidic ligands is provided, with an example of RGD-binding integrin ligands. It was recently demonstrated that the distinct modification of the guanidine group in these ligands allows for the selective modulation of the subtype (e.g., between the subtypes αv and α5). Moreover, a formerly unknown strategy for the functionalization via the guanidine group was demonstrated, and the synthetic approach is reviewed in this document...
April 27, 2017: Journal of Visualized Experiments: JoVE
https://www.readbyqxmd.com/read/28512781/developmental-regulation-and-localization-of-carnitine-palmitoyltransferases-cpts-in-rat-brain
#9
Jennifer N Jernberg, Caitlyn E Bowman, Michael J Wolfgang, Susanna Scafidi
While the brain's high energy demands are largely met by glucose, brain is also equipped with the ability to oxidize fatty acids for energy and metabolism. The brain expresses the carnitine palmitoyltransferases (CPTs) that mediate carnitine-dependent entry of long-chain acyl-CoAs into the mitochondrial matrix for β-oxidation - CPT1a and CPT2 located on the outer and inner mitochondrial membranes, respectively. Their developmental profile, regional distribution and activity as well as cell type expression remain unknown...
May 17, 2017: Journal of Neurochemistry
https://www.readbyqxmd.com/read/28511192/individual-variation-in-hunger-energy-intake-and-ghrelin-responses-to-acute-exercise
#10
James A King, Kevin Deighton, David R Broom, Lucy K Wasse, Jessica A Douglas, Stephen F Burns, Philip A Cordery, Emily S Petherick, Rachel L Batterham, Fernanda R Goltz, Alice E Thackray, Thomas Yates, David J Stensel
PURPOSE: This study aimed to characterize the immediate and extended effect of acute exercise on hunger, energy intake, and circulating acylated ghrelin concentrations using a large data set of homogenous experimental trials and to describe the variation in responses between individuals. METHODS: Data from 17 of our group's experimental crossover trials were aggregated yielding a total sample of 192 young, healthy males. In these studies, single bouts of moderate to high-intensity aerobic exercise (69% ± 5% V˙O2 peak; mean ± SD) were completed with detailed participant assessments occurring during and for several hours postexercise...
June 2017: Medicine and Science in Sports and Exercise
https://www.readbyqxmd.com/read/28510460/effects-of-membrane-defects-and-polymer-hydrophobicity-on-networking-kinetics-of-vesicles
#11
Yan Xia, Hyun-Sook Jang, Zhiqiang Shen, Geoffrey D Bothun, Ying Li, Mu-Ping Nieh
The kinetics of clustering unilamellar vesicles induced by inverse Pluronics, poly(propylene oxide)m-poly(ethylene oxide)n-poly(propylene oxide)m, POm-EOn-POm, were investigated via experiments and molecular dynamic simulations. Two important factors for controlling the networking kinetics are the membrane defects presumably located at the interfacial region between two lipid domains induced by acyl chain mismatch, and the polymer hydrophobicity. As expected, the clustering rate increases significantly with increasing bilayer defects on the membrane where the insertion of PPO is likely to take place because of the reduced energy barrier for the insertion of PO...
May 16, 2017: Langmuir: the ACS Journal of Surfaces and Colloids
https://www.readbyqxmd.com/read/28510438/complex-effects-of-24-1-sphingolipids-in-membranes-containing-dioleoyl-phosphatidylcholine-and-cholesterol
#12
Aritz B Garcia-Arribas, Emilio J Gonzalez-Ramirez, Jesús Sot, Itziar Areso, Alicia Alonso, Felix M Goni
The effects of C24:1 sphingolipids have been tested in phospholipid bilayers containing cholesterol. Confocal microscopy, differential scanning calorimetry, and atomic force microscopy imaging and force curves have been used. More precisely, the effects of C24:1 ceramide (nervonoyl ceramide, nCer) were evaluated and compared to those of C16:0 ceramide (palmitoyl ceramide, pCer) in bilayers composed basically of dioleoyl phosphatidylcholine, sphingomyelin (either C24:1, nSM or C16:0, pSM) and cholesterol. Combination of equimolecular amounts of C24:1 and C16:0 sphingolipids were also studied under the same conditions...
May 16, 2017: Langmuir: the ACS Journal of Surfaces and Colloids
https://www.readbyqxmd.com/read/28507694/a-convergent-synthesis-of-1-3-4-oxadiazoles-from-acyl-hydrazides-under-semiaqueous-conditions
#13
Kazuyuki Tokumaru, Jeffrey N Johnston
The 1,3,4-oxadiazole is an aromatic heterocycle valued for its low-lipophilicity in drug development. Substituents at the 2- and/or 5-positions can modulate the heterocycle's electronic and hydrogen bond-accepting capability, while exploiting its use as a carbonyl bioisostere. A new approach to 1,3,4-oxadiazoles is described wherein α-bromo nitroalkanes are coupled to acyl hydrazides to deliver the 2,5-disubstituted oxadiazole directly, avoiding a 1,2-diacyl hydrazide intermediate. Access to new building blocks of oxadiazole-substituted secondary amines is improved by leveraging chiral α-bromo nitroalkane or amino acid hydrazide substrates...
April 1, 2017: Chemical Science
https://www.readbyqxmd.com/read/28498670/palladium-catalyzed-aminocarbonylation-in-solid-phase-peptide-synthesis-a-method-for-capping-cyclization-and-isotope-labeling
#14
Anna Skogh, Stig D Friis, Troels Skrydstrup, Anja Sandström
A new synthetic approach for introducing N-capping groups onto peptides attached to a solid support, combining aminocarbonylation under mild conditions using a palladacycle precatalyst and solid-phase peptide synthesis, is reported. The use of a silacarboxylic acid as an in situ CO-releasing molecule allowed the reaction to be performed in a single vial. The method also enables versatile substitution of side chains, side-chain-to-side-chain cyclizations, and selective [(13)C] acyl labeling of modified peptides...
May 12, 2017: Organic Letters
https://www.readbyqxmd.com/read/28493495/silver-catalyzed-three-component-1-1-aminoacylation-of-homopropargylamines-dual-additions-between-terminal-alkynes-and-isocyanides
#15
Shuo Tong, Cyril Piemontesi, Qian Wang, Mei-Xiang Wang, Jieping Zhu
Reaction of secondary homopropargylamines, isocyanides and water in the presence of a catalytic amount of silver acetate followed by silica gel chromatography purification afforded substituted proline amides in good to excellent yields. Primary homopropargylamines underwent cyclizative Ugi-Joullié three-component reaction with isocyanides and carboxylic acids to afford functionalized N-acyl proline amides. High diastereoselectivity was observed in the synthesis of 4-alkoxy and 4,5-disubstituted proline derivatives...
May 11, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28492333/self-assembly-of-amphiphilic-biotransesterified-%C3%AE-cyclodextrins-supramolecular-structure-of-nanoparticles-and-surface-properties
#16
Jean-Luc Putaux, Christine Lancelon-Pin, Francois-Xavier Legrand, Marion Pastrello, Luc Choisnard, Annabelle Geze, Cyrille Rochas, Denis Wouessidjewe
A series of β-cyclodextrin (βCD) amphiphilic derivatives with varying degree of substitution was prepared by acylating βCDs on their secondary face using thermolysin to catalyze the transesterification. After dissolution in acetone, the βCD-Cn derivatives (n = 8, 10, 12, 14) were nanoprecipitated in water where they self-organized into structured particles which were characterized using cryo-transmission electron microscopy (cryo-TEM) images and small-angle X-ray scattering (SAXS) data. Two types of morphologies and ultrastructures were observed depending on the total degree of substitution (TDS) of the parent derivative...
May 11, 2017: Langmuir: the ACS Journal of Surfaces and Colloids
https://www.readbyqxmd.com/read/28487993/acinetobacter%C3%A2-baumannii-quorum-sensing-signalling-molecule-induces-the-expression-of-drug-resistance-genes
#17
Yi Dou, Fei Song, Feng Guo, Zengding Zhou, Cailian Zhu, Jun Xiang, Jingning Huan
Quorum-sensing signalling molecules such as N‑acyl homoserine lactones (AHLs) enable certain Gram‑negative bacteria to respond to environmental changes through behaviours, such as biofilm formation and flagellar movement. The present study aimed to identify Acinetobacter baumannii AHLs and assess their influence on antibiotic resistance. A clinical isolate of A. baumannii strain S (AbS) was collected from the wound of a burn patient and high‑performance liquid chromatography and tandem quadrupole or quadrupole time‑of‑flight high‑resolution mass spectrometry was used to identify AbS AHLs...
June 2017: Molecular Medicine Reports
https://www.readbyqxmd.com/read/28487430/rna-dependent-cysteine-biosynthesis-in-bacteria-and-archaea
#18
Takahito Mukai, Ana Crnković, Takuya Umehara, Natalia N Ivanova, Nikos C Kyrpides, Dieter Söll
The diversity of the genetic code systems used by microbes on earth is yet to be elucidated. It is known that certain methanogenic archaea employ an alternative system for cysteine (Cys) biosynthesis and encoding; tRNA(Cys) is first acylated with phosphoserine (Sep) by O-phosphoseryl-tRNA synthetase (SepRS) and then converted to Cys-tRNA(Cys) by Sep-tRNA:Cys-tRNA synthase (SepCysS). In this study, we searched all genomic and metagenomic protein sequence data in the Integrated Microbial Genomes (IMG) system and at the NCBI to reveal new clades of SepRS and SepCysS proteins belonging to diverse archaea in the four major groups (DPANN, Euryarchaeota, TACK, and Asgard) and two groups of bacteria ("Candidatus Parcubacteria" and Chloroflexi)...
May 9, 2017: MBio
https://www.readbyqxmd.com/read/28486967/pseudoxanthoma-elasticum
#19
REVIEW
Dominique P Germain
Pseudoxanthoma elasticum (PXE) is a genetic metabolic disease with autosomal recessive inheritance caused by mutations in the ABCC6 gene. The lack of functional ABCC6 protein leads to ectopic mineralization that is most apparent in the elastic tissues of the skin, eyes and blood vessels. The clinical prevalence of PXE has been estimated at between 1 per 100,000 and 1 per 25,000, with slight female predominance. The first clinical sign of PXE is almost always small yellow papules on the nape and sides of the neck and in flexural areas...
May 10, 2017: Orphanet Journal of Rare Diseases
https://www.readbyqxmd.com/read/28485149/trapping-of-transient-zwitterionic-intermediates-by-n-acylpyridinium-salts-a-palladium-catalyzed-diastereoselective-three-component-reaction
#20
Dan Zhang, Zhenghui Kang, Wenhao Hu
We developed a palladium-catalyzed diastereoselective three-component reaction of N-aryl diazoamides, pyridine, and chloroformate, which proceeded through trapping of transient zwitterionic intermediates by in situ formed N-acylpyridinium salts in a regioselective 1,4-addition fashion. This reaction can rapidly provide a library of biologically relevant 4-(2-oxoindolin-3-yl)-1,4-dihydropyridine derivatives in high yields (up to 98%) with moderate to excellent diastereoselectivities (up to >95:5 dr) under mild reaction conditions...
May 19, 2017: Journal of Organic Chemistry
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