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N-acyl or endocannnabanoid or NAPE

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https://www.readbyqxmd.com/read/29350930/curtin-hammett-driven-intramolecular-cyclization-of-heteroenyne-allenes-to-phenanthridine-fused-quinazoliniminiums
#1
Pamela S Filby, Sundeep Rayat
Intramolecular cyclization of the heteroenyne-allene, 2-((biphenyl-2-ylimino)methyleneamino)benzonitrile 1 to phenanthridine-fused quinazoliniminium salt PQ in the presence of a Lewis acid at room temperature involves formation of two new bonds: a C-C bond and a C-N bond. In this article, density functional theory (B3LYP and M06-2X) was employed in conjunction with 6-311G* basis set to gain insights into the mechanism of this cyclization reaction. The solvent effects were considered using Polarizable Continuum Model with nitromethane as the solvent...
January 19, 2018: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/29350449/lipoidal-corneal-degeneration-in-aged-falcons
#2
Bret A Moore, Joanne R Paul-Murphy, Kathleen L Adamson, Richard R Dubielzig, Thomas Kern, Ben J Gonzales, Peregrine Wolff, Christopher J Murphy
OBJECTIVE: To present a case series of idiopathic lipoidal corneal degeneration in falcons. ANIMALS STUDIED: Five falcons including three peregrine falcons (Falco peregrinus), one prairie falcon (Falco mexicanus), and one red-naped shaheen (Falco peregrinus babylonicus) were observed to develop slowly progressive corneal opacification that began at the temporal limbus and extended centripetally across the cornea over a period of years. Four of the birds were over 20 years old...
January 19, 2018: Veterinary Ophthalmology
https://www.readbyqxmd.com/read/29345807/targeting-a-dark-excited-state-of-hiv-1-nucleocapsid-by-anti-retroviral-thioesters-revealed-by-nmr
#3
Lalit Deshmukh, Vitali Tugarinov, Daniel H Appella, G Marius Clore
HIV-1 nucleocapsid (NCp7) is a two Cys2HisCys zinc knuckle (N-Zn and C-Zn) protein that plays a key role in viral replication. Here we characterize NCp7 conformational dynamics by NMR relaxation dispersion and chemical exchange saturation transfer measurements. While the N-Zn knuckle is conformationally stable, the C-Zn knuckle interconverts on the millisecond time scale between the major state, in which the zinc is coordinated by three cysteines and a histidine, and two folded minor species (with populations around 1%) in which one of the coordination bonds (Cys413-S---Zn or His421-N2---Zn) is hydrolysed...
January 18, 2018: Angewandte Chemie
https://www.readbyqxmd.com/read/29345707/synthesis-and-characterization-of-a-photocleavable-collagen-like-peptide
#4
Alfredo Ornelas, Kaitlyn N Williams, Kevin A Hatch, Aurelio Paez, Angela C Aguilar, Cameron C Ellis, Nishat Tasnim, Supriyo Ray, Carl W Dirk, Thomas Boland, Binata Joddar, Chunqiang Li, Katja Michael
A 34-amino acid long collagen-like peptide rich in proline, hydroxyproline, and glycine, and with four photoreactive N-acyl-7-nitroindoline units incorporated into the peptide backbone was synthesized by on-resin fragment condensation. Its circular dichroism supports a stable triple helix structure. The built-in photochemical function enables the decomposition of the peptide into small peptide fragments by illumination with UV light of 350 nm in aqueous solution. Illumination of a thin film of the peptide, or a thin film of a photoreactive amino acid model compound containing a 5-bromo-7-nitroindoline moiety, with femtosecond laser light at 710 nm allows for the creation of well-resolved micropatterns...
January 18, 2018: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/29345421/synthesis-of-histidine-containing-oligopeptides-via-histidine-promoted-peptide-ligation
#5
Kai-Jin Huang, Yi-Chen Huang, Yuya Angel Lin
Histidine-containing peptides are valuable therapeutic agents for treatment of neurodegenerative diseases. However, the synthesis of histidine-containing peptides is not trivial due to the potential of imidazole sidechain of histidine to act as a nucleophile if unprotected. A peptide ligation method utilizing the imidazole sidechain of histidine has been developed. The key imidazolate intermediate that acts as an internal acyl transfer catalyst during ligation is generated by deprotonation. Transesterification with amino acids or peptides tethered with C-terminal thioester followed by N to N acyl shifts led to the final ligated products...
January 18, 2018: Chemistry, An Asian Journal
https://www.readbyqxmd.com/read/29345136/regioselective-reaction-of-heterocyclic-n-oxides-an-acyl-chloride-and-cyclic-thioethers
#6
Przemyslaw Frei, D Heulyn Jones, Steven T Kay, Jayde A McLellan, Blair F Johnston, Alan R Kennedy, Nicholas C O Tomkinson
Treatment of electron deficient pyridine N-oxides with 4-nitrobenzoyl chloride and a cyclic thioether in the presence of triethylamine leads to the corresponding 2-functionalized product in up to a 74% isolated yield. The transformation can also be accomplished with alternative nitrogen containing heterocycles, including quinolines, pyrimidines, and pyrazines. To expand the scope of the transformation, diisopropyl ether can be used as the reaction medium to allow for the use of solid thioether substrates.
January 18, 2018: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/29343058/biosynthesis-of-long-chain-n-acyl-amide-by-a-truncated-pks-nrps-hybrid-megasynthase-in-fungi
#7
Yang Hai, Yi Tang
Truncated PKS-NRPS megasynthases in which only the C-domain is present are widespread in fungi, yet nearly all members have unknown functions. Bioinformatics analysis showed that the C domains of such PKS-C enzymes are noncanonical due to substitu-tion at the second histidine in the active site HHxxxDG motif. Here, we used genome mining strategy to characterize a cryptic PKS-C hybrid from Talaromyces wortmanii and discovered the products are reduced long chain polyketides amidated with a specif-ic ω-amino acid 5-aminopentanoic acid (5PA)...
January 17, 2018: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/29341610/visible-light-mediated-ipso-carboacylation-of-alkynes-synthesis-of-3-acylspiro-4-5-trienones-from-n-p-methoxyaryl-propiolamides-and-acyl-chlorides
#8
Yu Liu, Qiao-Lin Wang, Cong-Shan Zhou, Biquan Xiong, Pan-Liang Zhang, Chang-An Yang, Ke-Wen Tang
A novel visible-light-mediated ipso-carboacylation of N-(p-methoxyaryl)propiolamides with acyl chloride has been established for the synthesis of diverse 3-acylspiro[4,5]trienones with high selectivity and efficiency. This method represents a new difunctionalization of alkynes through cross coupling of the acyl chloride C-Cl bonds with an ipso-aromatic carbon by simultaneously forming two new carbon-carbon bonds and one carbon-oxygen double bond.
January 17, 2018: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/29339490/structural-basis-of-sterol-recognition-and-nonvesicular-transport-by-lipid-transfer-proteins-anchored-at-membrane-contact-sites
#9
Junsen Tong, Mohammad Kawsar Manik, Young Jun Im
Membrane contact sites (MCSs) in eukaryotic cells are hotspots for lipid exchange, which is essential for many biological functions, including regulation of membrane properties and protein trafficking. Lipid transfer proteins anchored at membrane contact sites (LAMs) contain sterol-specific lipid transfer domains [StARkin domain (SD)] and multiple targeting modules to specific membrane organelles. Elucidating the structural mechanisms of targeting and ligand recognition by LAMs is important for understanding the interorganelle communication and exchange at MCSs...
January 16, 2018: Proceedings of the National Academy of Sciences of the United States of America
https://www.readbyqxmd.com/read/29338235/enantioselective-dearomatization-of-alkyl-pyridiniums-by-n-heterocyclic-carbene-catalyzed-nucleophilic-acylation
#10
Graziano Di Carmine, Daniele Ragno, Olga Bortolini, Pier Paolo Giovannini, Andrea Mazzanti, Alessandro Massi, Marco Fogagnolo
A chiral-NHC-catalyzed dearomatizing reaction of activated N-alkylpyridinium salts with aliphatic aldehydes is described. The resulting acylated 1,4-dihydropyridines have been obtained with complete C4 regioselectivity and enantioselectivities in the range of 52-78% ee. The (4R) absolute configuration of the synthesized compounds has been determined by TD-DFT simulation of the electronic circular dichroism spectra.
January 16, 2018: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/29336543/histone-deacetylase-11-is-a-fatty-acid-deacylase
#11
Zsofia Kutil, Zora Novakova, Marat Meleshin, Jana Mikesova, Mike Schutkowski, Cyril Barinka
Histone deacetylase 11 (HDAC11) is a sole member of the class IV HDAC subfamily with negligible intrinsic deacetylation activity. Here we report in vitro profiling of HDAC11 deacylase activities, and our data unequivocally show that the enzyme efficiently removes acyl moieties spanning 8-18 carbons from the side chain nitrogen of the lysine residue of a peptidic substrate. Additionally, N-linked lipoic acid and biotin are removed by the enzyme, although with lower efficacy. Catalytic efficiencies toward dodecanoylated and myristoylated peptides were 77,700 M-1s-1 and 149,000 M-1s-1, respectively, making HDAC11 the most proficient fatty acid deacylase of the HDAC family...
January 16, 2018: ACS Chemical Biology
https://www.readbyqxmd.com/read/29332142/purification-and-characterization-of-a-novel-organic-solvent-tolerant-and-cold-adapted-lipase-from-psychrobacter-sp-zy124
#12
Yue Zhang, Fangling Ji, Jingyun Wang, Zhongji Pu, Bo Jiang, Yongming Bao
By screening 25 different psychrophilic strains isolated from the Arctic habitat, we isolated a strain capable of producing lipase. We identified this strain as Psychrobacter sp. ZY124 based on the amplified 16S rDNA sequence. The lipase, named as Lipase ZC12, produced from the supernatant of Psychrobacter sp. ZY124 cultured at 15 °C was purified to homogeneity by ammonium sulfate precipitation followed by Phenyl Sepharose FF gel hydrophobic chromatography. Based on the obtained amino acid sequence, Lipase ZC12 is classified as a member of the Proteus/psychrophilic subfamily of lipase family I...
January 13, 2018: Extremophiles: Life Under Extreme Conditions
https://www.readbyqxmd.com/read/29330355/fatty-acids-and-related-lipid-mediators-in-the-regulation-of-cutaneous-inflammation
#13
REVIEW
Magdalena Kiezel-Tsugunova, Alexandra C Kendall, Anna Nicolaou
Human skin has a distinct profile of fatty acids and related bioactive lipid mediators that regulate many aspects of epidermal and dermal homeostasis, including immune and inflammatory reactions. Sebum lipids act as effective antimicrobial agents, shape immune cell communications and contribute to the epidermal lipidome. The essential fatty acid linoleic acid is crucial for the structure of the epidermal barrier, while polyunsaturated fatty acids act as precursors to eicosanoids, octadecanoids and docosanoids through cyclooxygenase, lipoxygenase and cytochrome P450 monooxygenase-mediated reactions, and endocannabinoids and N-acyl ethanolamines...
January 12, 2018: Biochemical Society Transactions
https://www.readbyqxmd.com/read/29329269/design-synthesis-and-safener-activity-of-novel-methyl-r-n-benzoyl-dichloroacetyl-thiazolidine-4-carboxylates
#14
Li-Xia Zhao, Hao Wu, Yue-Li Zou, Qing-Rui Wang, Ying Fu, Chun-Yan Li, Fei Ye
A series of novel methyl (R)-N-benzoyl/dichloroacetyl-thiazolidine-4-carboxylates were designed by active substructure combination. The title compounds were synthesized using a one-pot route from l-cysteine methyl ester hydrochloride, acyl chloride, and ketones. All compounds were characterized by IR, ¹H NMR, 13C NMR, and HRMS. The structure of 4q was determined by X-ray crystallography. The biological tests showed that the title compounds protected maize from chlorimuron-ethyl injury to some extent. The ALS activity assay showed that the title compounds increased the ALS activity of maize inhibited by chlorimuron-ethyl...
January 12, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/29328480/acylated-and-unacylated-ghrelin-inhibit-apoptosis-in-myoblasts-cocultured-with-colon-carcinoma-cells
#15
Xianliang Zeng, Sizeng Chen, Yanfeng Lin, Zhao Ke
Cancer cachexia is a life‑threatening syndrome associated with myofiber damage. Tumor factors impair muscle regeneration by promoting myoblast apoptosis. Ghrelin is a multifunctional hormone with an anti‑apoptotic effect, but its mechanism of action is not fully understood. In the present study, we investigated whether the coculturing of C2C12 myoblasts with CT26 colon carcinoma cells may induce myoblast apoptosis, and whether acylated ghrelin (AG) and unacylated ghrelin (UnAG) may exert anti‑apoptotic effects...
January 12, 2018: Oncology Reports
https://www.readbyqxmd.com/read/29325553/sitagliptin-improved-glucose-assimilation-in-detriment-of-fatty-acid-utilization-in-experimental-type-ii-diabetes-role-of-glp-1-isoforms-in-glut4-receptor-trafficking
#16
E Ramírez, B Picatoste, A González-Bris, M Oteo, F Cruz, A Caro-Vadillo, J Egido, J Tuñón, M A Morcillo, Ó Lorenzo
BACKGROUND: The distribution of glucose and fatty-acid transporters in the heart is crucial for energy consecution and myocardial function. In this sense, the glucagon-like peptide-1 (GLP-1) enhancer, sitagliptin, improves glucose homeostasis but it could also trigger direct cardioprotective actions, including regulation of energy substrate utilization. METHODS: Type-II diabetic GK (Goto-Kakizaki), sitagliptin-treated GK (10 mg/kg/day) and wistar rats (n = 10, each) underwent echocardiographic evaluation, and positron emission tomography scanning for [18F]-2-fluoro-2-deoxy-D-glucose (18FDG)...
January 11, 2018: Cardiovascular Diabetology
https://www.readbyqxmd.com/read/29322975/atlantoaxial-instability-associated-with-pan-cervical-vertebral-fusion-report-on-management-of-4-cases
#17
Abhidha Shah, Amol Kaswa, Sonal Jain, Atul Goel
We report a series of four patients aged 4, 5, 14, and 27 years (1 male and 3 female patients) with severe shortening of the neck and torticollis since early childhood who presented with complaint of pain in the nape of neck as the primary symptom. All four patients had relatively well preserved neurological functions. One patient had vertical mobile and reducible atlantoaxial dislocation, and 3 patients had anteroposterior mobile and reducible dislocation. There was assimilation of atlas in 1 patient. The arch of atlas was bifid in 3 patients...
January 2018: Neurology India
https://www.readbyqxmd.com/read/29320681/intrinsic-curvature-mediated-transbilayer-coupling-in-asymmetric-lipid-vesicles
#18
Barbara Eicher, Drew Marquardt, Frederick A Heberle, Ilse Letofsky-Papst, Gerald N Rechberger, Marie-Sousai Appavou, John Katsaras, Georg Pabst
We measured the effect of intrinsic lipid curvature, J0, on structural properties of asymmetric vesicles made of palmitoyl-oleoyl-phosphatidylethanolamine (POPE; J0<0) and palmitoyl-oleoyl-phosphatidylcholine (POPC; J0∼0). Electron microscopy and dynamic light scattering were used to determine vesicle size and morphology, and x-ray and neutron scattering, combined with calorimetric experiments and solution NMR, yielded insights into leaflet-specific lipid packing and melting processes. Below the lipid melting temperature we observed strong interleaflet coupling in asymmetric vesicles with POPE inner bilayer leaflets and outer leaflets enriched in POPC...
January 9, 2018: Biophysical Journal
https://www.readbyqxmd.com/read/29320462/unsaturated-fatty-acids-affect-quorum-sensing-communication-system-and-inhibit-motility-and-biofilm-formation-of-acinetobacter-baumannii
#19
Marion Nicol, Stéphane Alexandre, Jean-Baptiste Luizet, Malena Skogman, Thierry Jouenne, Suzana P Salcedo, Emmanuelle Dé
The increasing threat of Acinetobacter baumannii as a nosocomial pathogen is mainly due to the occurrence of multidrug-resistant strains that are associated with the real problem of its eradication from hospital wards. The particular ability of this pathogen to form biofilms contributes to its persistence, increases antibiotic resistance, and promotes persistent/device-related infections. We previously demonstrated that virstatin, which is a small organic compound known to decrease virulence of Vibrio cholera via an inhibition of T4-pili expression, displayed very promising activity to prevent A...
January 10, 2018: International Journal of Molecular Sciences
https://www.readbyqxmd.com/read/29319258/familial-lecithin-cholesterol-acyl-transferase-deficiency-with-chronic-kidney-disease
#20
N Gopalakrishnan, R Arul, J Dhanapriya, T Dinesh Kumar, R Sakthirajan, T Balasubramaniyan
Familial lecithin-cholesterol acyltransferase (LCAT) deficiency is a rare autosomal recessive (AR) disease caused by mutation in the LCAT gene. LCAT enzyme esterifies cholesterol molecules in high-density lipoprotein(HDL) and low density-lipoprotein (LDL) particles. This enzyme deficiency is characterised by progressive corneal opacification, glomerulopathy, mild - moderate haemolytic anaemia and very low plasma levels of HDL. We here report a 34 year-old lady who presented with hypertension, nephrotic proteinuria, renal failure, corneal ring opacities, anemia and dyslipidemia...
October 2017: Journal of the Association of Physicians of India
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