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N-acyl or endocannnabanoid or NAPE

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https://www.readbyqxmd.com/read/28225111/cubr-tbhp-mediated-synthesis-of-n-acyl-sulfonimidamides-via-the-oxidative-cross-coupling-of-sulfonimidamides-and-aldehydes
#1
Ganesh Chandra Nandi, Cijil Raju
N-Acyl sulfonimidamides were synthesized via a Cu-catalyzed double C-H/N-H activation protocol. The imino end of sulfonimidamides was acylated using aldehyde as the acylating agent and t-butyl hydrogen peroxide (TBHP) as the oxidant in acetonitrile (MeCN) at 82 °C. The mild reaction conditions afforded low-to-moderate yields of N-acyl sulfonimidamides with high structural diversity.
February 22, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28225085/aidp-a-novel-n-acyl-homoserine-lactonase-gene-from-antarctic-planococcus-sp
#2
Wah Seng See-Too, Robson Ee, Yan-Lue Lim, Peter Convey, David A Pearce, Wai-Fong Yin, Kok-Gan Chan
Planococcus is a Gram-positive halotolerant bacterial genus in the phylum Firmicutes, commonly found in various habitats in Antarctica. Quorum quenching (QQ) is the disruption of bacterial cell-to-cell communication (known as quorum sensing), which has previously been described in mesophilic bacteria. This study demonstrated the QQ activity of a psychrotolerant strain, Planococcus versutus strain L10.15(T), isolated from a soil sample obtained near an elephant seal wallow in Antarctica. Whole genome analysis of this bacterial strain revealed the presence of an N-acyl homoserine lactonase, an enzyme that hydrolyzes the ester bond of the homoserine lactone of N-acyl homoserine lactone (AHLs)...
February 22, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28223925/effects-of-intermittent-alcohol-exposure-on-emotion-and-cognition-a-potential-role-for-the-endogenous-cannabinoid-system-and-neuroinflammation
#3
Laura Sanchez-Marin, Francisco J Pavon, Juan Decara, Juan Suarez, Ana Gavito, Estela Castilla-Ortega, Fernando Rodriguez de Fonseca, Antonia Serrano
Intermittent alcohol exposure is a common pattern of adolescent alcohol use that can lead to binge drinking episodes. Alcohol use is known to modulate the endocannabinoid system (ECS), which is involved in neuronal communication, neuroplasticity, neuroinflammation and behavior. Adolescent male Wistar rats were exposed to 4-week intermittent alcohol intoxication (3 g/kg injections for 4 days/week) or saline (N = 12 per group). After alcohol deprivation, adult rats were assessed for emotionality and cognition and the gene expression of the ECS and other factors related to behavior and neuroinflammation was examined in the brain...
2017: Frontiers in Behavioral Neuroscience
https://www.readbyqxmd.com/read/28221034/regioselective-1-4-conjugate-addition-of-grignard-reagents-to-%C3%AE-%C3%AE-%C3%AE-%C3%AE-dienones-and-%C3%AE-%C3%AE-%C3%AE-%C3%AE-dienyl-thiol-esters
#4
Emmanuel Amoah, R Karl Dieter
Alkyl Grignard reagents (Et, nBu, iPr, cyclohexyl), with the exception of tBuMgCl, undergo exclusive or exceptionally highly regioselective 1,4-addition reactions to α,β-γ,δ-unsaturated ketones, while aryl and heteroaryl Grignard reagents give mixed results ranging from exclusive 1,4-addition (1-naphthyl, 2-N-methylpyrrolyl) to regioselective 1,2-addition (2-furyl, 2:1). All alkyl, aryl, and heteroaryl Grignard reagents examined gave exclusive 1,4-addition reactions with α,β-γ,δ-unsaturated thiol esters, with the exception of tBuMgCl which gave an 80:20 mixture of 1,4-:1,6-addition products...
February 21, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28219782/characterization-of-phospholipid-nitroxidation-by-lc-ms-in-biomimetic-models-and-in-h9c2-myoblast-using-a-lipidomic-approach
#5
Tânia Melo, Pedro Domingues, Teresa M Ribeiro-Rodrigues, Henrique Girão, Marcela A Segundo, M Rosário M Domingues
Under nitroxidative stress conditions, lipids are prone to be modified by reaction with reactive nitrogen species (RNS) and different modifications were reported to occur in fatty acids. However, in the case of phospholipids (PL) studied under nitroxidative stress conditions, only nitroalkene derivatives of phosphatidylcholine (PC) and phosphatidylethanolamine (PE), were reported when using both in vitro biomimetic conditions and in vivo model system of type 1 diabetes mellitus. Therefore, in order to further explore other nitroxidative modifications of PL, a biomimetic model of nitroxidation combined with liquid chromatography mass spectrometry (MS) and MS/MS approaches were used to characterize the nitrated and nitroxidized derivatives of PCs and PEs...
February 17, 2017: Free Radical Biology & Medicine
https://www.readbyqxmd.com/read/28209057/saturated-fatty-acid-analogues-of-cell-penetrating-peptide-pepfect14-role-of-fatty-acid-modification-in-complexation-and-delivery-of-splice-correcting-oligonucleotides
#6
Tõnis Lehto, Luis Vasconcelos, Helerin Margus, Ricardo Figueroa, Margus Pooga, Mattias Hällbrink, Ulo Langel
Modifying cell-penetrating peptides (CPPs) with fatty acids has long been used to improve peptide-mediated nucleic acid delivery. In this study we have revisited this phenomenon with a systematic approach where we developed a structure-activity relationship to describe the role of the acyl chain length in the transfection process. For that we took a well-studied CPP, PepFect14, as the basis and varied its N-terminal acyl chain length from 2 to 22 carbons. To evaluate the delivery efficiency, the peptides were non-covalently complexed with a splice-correcting oligonucleotide (SCO) and tested in the HeLa pLuc705 reporter cell line...
February 17, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28199087/expression-purification-and-properties-of-a-human-arachidonoyl-specific-isoform-of-diacylglycerol-kinase
#7
William Jennings, Sejal Doshi, Prasanta Kumar Hota, Aaron Prodeus, Stephanie Black, Richard M Epand
Diacylglycerol kinase epsilon (DGKε) catalyzes the phosphorylation of diacylglycerol producing phosphatidic acid. DGKε demonstrates exquisite specificity for the acyl chains of diacylglycerol. This contributes to the specificity of the PI-cycle for lipid intermediates containing particular acyl chains. Dysregulation of DGKε perturbs lipid signaling and biosynthesis, which has been linked to epilepsy, Huntington's disease and heart disease. Recessive loss-of-function mutations in the DGKε gene cause atypical hemolytic uremic syndrome...
February 15, 2017: Biochemistry
https://www.readbyqxmd.com/read/28197928/enhanced-reactivity-in-nucleophilic-acyl-substitution-ion-ion-reactions-using-triazole-ester-reagents
#8
Jiexun Bu, Zhou Peng, Feifei Zhao, Scott A McLuckey
The acyl substitution reactions between 1-hydroxy-7-aza-benzotriazole (HOAt)/1-hydroxy-benzotriazole (HOBt) ester reagents and nucleophilic side chains on peptides have been demonstrated in the gas phase via ion/ion reactions. The HOAt/HOBt ester reagents were synthesized in solution and ionized via negative nano-electrospray ionization. The anionic reagents were then reacted with doubly protonated model peptides containing amines, guanidines, and imidazoles in the gas phase. The complexes formed in the reaction cell were further probed with ion trap collision induced dissociation (CID) yielding either a covalently modified analyte ion or a proton transfer product ion...
February 14, 2017: Journal of the American Society for Mass Spectrometry
https://www.readbyqxmd.com/read/28197135/cloning-and-characterization-of-the-autoinducer-synthase-gene-from-lipid-degrading-bacterium-cedecea-neteri
#9
Kian-Hin Tan, Kah-Yan How, Jia-Yi Tan, Wai-Fong Yin, Kok-Gan Chan
The process of intercellular communication among bacteria, termed quorum sensing (QS), is mediated by small diffusible molecules known as the autoinducers. QS allows the population to react to the change of cell density in unison, in processes such as biofilm formation, plasmid conjugation, virulence, motility and root nodulation. In Gram-negative proteobacteria, N-acyl homoserine lactone (AHL) is the common "language" to coordinate gene expression. This signaling molecule is usually synthesized by LuxI-type proteins...
2017: Frontiers in Microbiology
https://www.readbyqxmd.com/read/28193150/maleimide-scavenging-enhances-determination-of-protein-s-palmitoylation-state-in-acyl-exchange-methods
#10
Charlotte H Hurst, Dionne Turnbull, Fiona Plain, William Fuller, Piers A Hemsley
S-palmitoylation (S-acylation) is emerging as an important dynamic post-translational modification of cysteine residues within proteins. Current assays for protein S-palmitoylation involve either in vivo labeling or chemical cleavage of S-palmitoyl groups to reveal a free cysteine sulfhydryl that can be subsequently labeled with an affinity handle (acyl-exchange). Assays for protein S-palmitoylation using acyl-exchange chemistry therefore require blocking of non-S-palmitoylated cysteines, typically using N-ethylmaleimide (NEM), to prevent non-specific detection...
February 1, 2017: BioTechniques
https://www.readbyqxmd.com/read/28191598/diacylglycerol-kinase-%C3%AE%C2%B5-localizes-to-subsurface-cisterns-of-cerebellar-purkinje-cells
#11
Yasukazu Hozumi, Hiroki Fujiwara, Kenya Kaneko, Satoshi Fujii, Matthew K Topham, Masahiko Watanabe, Kaoru Goto
Following activation of Gq protein-coupled receptors, phospholipase C yields a pair of second messengers: diacylglycerol (DG) and inositol 1,4,5-trisphosphate. Diacylglycerol kinase (DGK) phosphorylates DG to produce phosphatidic acid, another second messenger. Of the DGK family, DGKε is the only DGK isoform that exhibits substrate specificity for DG with an arachidonoyl acyl chain at the sn-2 position. Recently, we demonstrated that hydrophobic residues in the N-terminus of DGKε play an important role in targeting the endoplasmic reticulum in transfected cells...
February 13, 2017: Cell and Tissue Research
https://www.readbyqxmd.com/read/28183264/ellagitannins-bioavailability-purification-and-biotechnological-degradation
#12
Pedro Aguilar-Zárate, Jorge E Wong-Paz, Juan J Buenrostro-Figueroa, Juan A Ascacio, Juan C Contreras-Esquivel, Cristóbal N Aguilar
The ellagitannins are a group of phenolic compounds with biological activities. The ellagic acid is the product obtained from hydrolysis of ellagitannins. Information related to the biosynthesis of ellagitannins still been scarce and confused. The ellagitannins are obtained from plants and their purification process implies mainly the use of chromatographic techniques. The ellagitannin acyl hydrolase (EAH) also known as ellagitannase is an enzyme capable to hydrolyze the ester bonds of ellagitannins and the consequent releasing of ellagic acid...
February 8, 2017: Mini Reviews in Medicinal Chemistry
https://www.readbyqxmd.com/read/28180946/new-developments-and-directions-in-the-clinical-application-of-the-echinocandins
#13
REVIEW
C C Chang, M A Slavin, S C-A Chen
The echinocandins-caspofungin, anidulafungin and micafungin-are semi-synthetic cyclic hexapeptide antimicrobial agents with modified N-linked acyl lipid side chains which anchor the compounds to the phospholipid bilayer of the fungal cell membrane, thereby inhibiting synthesis of fungal cell wall glucan. Over the last 10 years, echinocandins have become the first-line antifungal treatment of candidaemia and other forms of invasive candidiasis (IC). Echinocandins are generally well tolerated, but their use is limited by their requirement for daily intravenous dosing, lack of oral formulation and limited spectrum...
February 8, 2017: Archives of Toxicology
https://www.readbyqxmd.com/read/28173026/p780-3-oxo-c12-2-hsl-a-new-n-acyl-homoserine-lactone-identified-in-gut-ecosystem-exerts-an-anti-inflammatory-effect-and-does-not-modify-paracellular-permeability
#14
E Le Balc'h, C Landman, E Tauziet, L Brot, E Quevrain, D Rainteau, J-P Grill, S Thenet, P Seksik
No abstract text is available yet for this article.
February 1, 2017: Journal of Crohn's & Colitis
https://www.readbyqxmd.com/read/28169479/helical-oligopeptides-of-a-quaternized-amino-acid-with-tunable-chiral-induction-ability-and-an-anomalous-ph-response
#15
Joonil Cho, Yasuhiro Ishida, Takuzo Aida
A series of octamer (8mer) and hexadecamer (16mer) oligopeptides of 4-aminopiperidine-4-carboxylic acid (Api) with L-leucine as a chiral auxiliary at their N- or C-termini were synthesized. Using circular dichroism spectroscopy, the conformational profiles of the peptides were systematically studied, which revealed that the α-helix formation ability of the peptides is determined by the combination of parameters including peptide length, state of the piperidine groups in the Api units, and position of the chiral auxiliary...
February 7, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28167162/disparate-response-to-microoxia-and-nitrogen-oxides-of-the-bradyrhizobium-japonicum-napedabc-nirk-and-norcbqd-denitrification-genes
#16
Emilio Bueno, Eloy F Robles, María J Torres, Tino Krell, Eulogio J Bedmar, María J Delgado, Socorro Mesa
Expression of the Bradyrhizobium japonicum napEDABC, nirK and norCBQD denitrification genes requires low oxygen (O2) tension and nitrate (NO3(-)), through a regulatory network comprised of two coordinated cascades, FixLJ-FixK2-NnrR and RegSR-NifA. To precisely understand how these signals are integrated in the FixLJ-FixK2-NnrR circuit, we analyzed β-Galactosidase activities from napE-lacZ, nirK-lacZ and norC-lacZ fusions and performed analyses of NapC and NorC levels as well as periplasmic nitrate reductase (Nap) activity, in B...
February 3, 2017: Nitric Oxide: Biology and Chemistry
https://www.readbyqxmd.com/read/28166636/cartilaginous-metabolomic-study-reveals-potential-mechanisms-of-osteophyte-formation-in-osteoarthritis
#17
Zhongwei Xu, Tingmei Chen, Jiao Luo, Shijia Ding, Sichuan Gao, Jian Zhang
Osteophyte is one of the inevitable consequences of progressive osteoarthritis with the main characteristics of cartilage degeneration and endochondral ossification. The pathogenesis of osteophyte formation is not fully understood to date. In this work, metabolomic approaches were employed to explore potential mechanisms of osteophyte formation by detecting metabolic variations between extracts of osteophyte cartilage tissues (n = 32) and uninvolved control cartilage tissues (n = 34), based on the platform of ultraperformance liquid chromatography tandem quadrupole time-of-flight mass spectrometry, as well as the use of multivariate statistic analysis and univariate statistic analysis...
February 21, 2017: Journal of Proteome Research
https://www.readbyqxmd.com/read/28164039/quorum-sensing-n-acyl-homoserine-lactones-sdia-suppresses-escherichia-coli-pseudomonas-aeruginosa-conjugation-through-inhibiting-trai-expression
#18
Yang Lu, Jianming Zeng, Binning Wu, Shunmei E, Lina Wang, Renxin Cai, Ni Zhang, Youqiang Li, Xianzhang Huang, Bin Huang, Cha Chen
Conjugation is a key mechanism for horizontal gene transfer and plays an important role in bacterial evolution, especially with respect to antibiotic resistance. However, little is known about the role of donor and recipient cells in regulation of conjugation. Here, using an Escherichia coli (SM10λπ)-Pseudomonas aeruginosa (PAO1) conjugation model, we demonstrated that deficiency of lasI/rhlI, genes associated with generation of the quorum sensing signals N-acyl homoserine lactones (AHLs) in PAO1, or deletion of the AHLs receptor SdiA in the donor SM10λπ both facilitated conjugation...
2017: Frontiers in Cellular and Infection Microbiology
https://www.readbyqxmd.com/read/28158925/mirnas-in-human-subcutaneous-adipose-tissue-effects-of-weight-loss-induced-by-hypocaloric-diet-and-exercise
#19
Malene M Kristensen, Peter K Davidsen, Andreas Vigelsø, Christina N Hansen, Lars J Jensen, Niels Jessen, Jens M Bruun, Flemming Dela, Jørn W Helge
OBJECTIVE: Obesity is central in the development of insulin resistance. However, the underlying mechanisms still need elucidation. Dysregulated microRNAs (miRNAs; post-transcriptional regulators) in adipose tissue may present an important link. METHODS: The miRNA expression in subcutaneous adipose tissue from 19 individuals with severe obesity (10 women and 9 men) before and after a 15-week weight loss intervention was studied using genome-wide microarray analysis...
February 3, 2017: Obesity
https://www.readbyqxmd.com/read/28156101/mycobacteria-encode-active-and-inactive-classes-of-tesb-fatty-acyl-coa-thioesterases-revealed-through-structural-and-functional-analysis
#20
Crystall M D Swarbrick, Glennon V Bythrow, David Guerra Aragão, Gabrielle A Germain, Luis E N Quadri, Jade K Forwood
Mycobacteria contain a large number of highly divergent species, and exhibit unusual lipid metabolism profiles, believed to play important roles in immune invasion. Thioesterases modulate lipid metabolism through the hydrolysis of activated fatty-acyl CoAs, and multiple copies are present in mycobacteria, yet many remain uncharacterized. Here, we undertake a comprehensive structural and functional analysis of a TesB thioesterase from Mycobacterium avium (MaTesB). Structural superposition with other TesB thioesterases reveal that the Asp active site residue, highly conserved across a wide range of TesB thioesterases, is mutated to Ala...
February 3, 2017: Biochemistry
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