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N-acyl or endocannnabanoid or NAPE

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https://www.readbyqxmd.com/read/28092360/chemical-proteomics-reveals-adp-ribosylation-of-small-gtpases-during-oxidative-stress
#1
Nathan P Westcott, Joseph P Fernandez, Henrik Molina, Howard C Hang
ADP-ribosylation is a post-translational modification that is known to be involved in cellular homeostasis and stress but has been challenging to analyze biochemically. To facilitate the detection of ADP-ribosylated proteins, we show that an alkyne-adenosine analog, N(6)-propargyl adenosine (N(6)pA), is metabolically incorporated in mammalian cells and enables fluorescence detection and proteomic analysis of ADP-ribosylated proteins. Notably, our analysis of N(6)pA-labeled proteins that are upregulated by oxidative stress revealed differential ADP-ribosylation of small GTPases...
January 16, 2017: Nature Chemical Biology
https://www.readbyqxmd.com/read/28091672/a-rapid-way-to-discover-nonstandard-macrocyclic-peptide-modulators-of-drug-targets
#2
Toby Passioura, Hiroaki Suga
Studies of the fundamental nature of RNA catalysis and the potential mechanism of a shift from the "RNA world" to proteinaceous life lead us to identify a set of ribozymes (flexizymes) capable of promiscuous tRNA acylation. Whilst theoretically and mechanistically interesting in their own right, flexizymes have turned out to have immense practical value for the simple synthesis of tRNAs acylated with unusual amino acids, which in turn can be used for the ribosomal synthesis of peptides containing non-canonical residues...
January 16, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28090775/reaction-of-push-pull-enaminoketones-and-in-situ-generated-ortho-quinone-methides-synthesis-of-3-acyl-4h-chromenes-and-2-acyl-1h-benzo-f-chromenes-as-precursors-for-hydroxybenzylated-heterocycles
#3
Anton Vladimirovich Lukashenko, Vitaly Aleksandrovich Osyanin, Dmitry Vladimirovich Osipov, Yuri N Klimochkin
A simple and efficient method for the synthesis of 4H-chromenes and 1H-benzo[f]chromenes containing trifluoroacetyl or aroyl group in pyran ring from o-quinone methide precursors and push-pull enaminoketones has been developed. The chromenes are presumably formed through an initial oxa-Diels-Alder reaction followed by an elimination of amine. Possibility of further transformations of given chromenes to o-hydroxybenzylated pyrazoles, isoxazoles and pyridines has been demonstrated.
January 16, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28089692/in-vitro-bioaccessibility-of-the-marine-biotoxins-okadaic-acid-dinophysistoxin-2-and-their-7-o-acyl-fatty-acid-ester-derivatives-in-raw-and-steamed-shellfish
#4
Diana Manita, Ricardo N Alves, Ana Catarina Braga, Fabiola Fogaça, António Marques, Pedro Reis Costa
Okadaic acid (OA), Dinophysistoxins (DTX1 and DTX2) and their acyl-derivatives (DTX3) are marine toxins responsible for the human diarrhetic shellfish poisoning. To date the amount of toxins ingested from consumption of shellfish has been considered equal to the amount of toxins available for uptake by the human body. The aim of this study is to assess the OA, DTX2 and DTX3 fractions released from raw and steamed mussels and cockles into the digestive fluids (bioaccessibility) using a static in vitro digestion model...
January 12, 2017: Food and Chemical Toxicology
https://www.readbyqxmd.com/read/28087611/production-of-n-acyl-homoserine-lactones-by-the-sponge-associated-marine-actinobacteria-salinispora-arenicola-and-salinispora-pacifica
#5
Utpal Bose, Catharine A Ortori, Sarir Sarmad, David A Barrett, Amitha K Hewavitharana, Mark P Hodson, John A Fuerst, P Nicholas Shaw
The structures of acyl homoserine lactone (AHL) compounds and their quantification was accomplished using an integrated liquid chromatography-mass spectrometry approach. The precursor and product ions, along with retention times of peaks, were searched against an in-house database of AHLs and structures confirmed by accurate mass and by comparison with authentic AHL standards. The two compounds, N-(3-oxodecanoyl)-L-homoserine lactone and N-(3-oxododecanoyl)-L-homoserine lactone were characterised and quantified in Salinispora sp...
January 12, 2017: FEMS Microbiology Letters
https://www.readbyqxmd.com/read/28087335/the-lower-alkyl-methacrylates-genotoxic-profile-of-non-carcinogenic-compounds
#6
Richard J Albertini
All of the lower alkyl methacrylates are high production chemicals with potential for human exposure. The genotoxicity of seven mono-functional alkyl esters of methacrylic acid, i.e. methyl methacrylate, ethyl methacrylate, hydroxyethyl methacrylate, n-, i- and t-butyl methacrylate and 2 ethyl hexyl methacrylate, as well as methacrylic acid itself, the acyl component common to all, is reviewed and compared with the lack of carcinogenicity of methyl methacrylate, the representative member of the series so evaluated...
January 10, 2017: Regulatory Toxicology and Pharmacology: RTP
https://www.readbyqxmd.com/read/28076955/post-translational-modifications-of-trypanosoma-cruzi-canonical-and-variant-histones
#7
Gisele F A Picchi, Vanessa Zulkievicz, Marco Aurelio Krieger, Nilson T Zanchin, Samuel Goldenberg, Lyris M F de Godoy
Chagas disease, caused by Trypanosoma cruzi, still affects millions of people around the world. No vaccines neither treatment for chronic Chagas disease are available, and chemotherapy for the acute phase is hindered by limited efficacy and severe side effects. The processes by which the parasite acquires infectivity and survives in different hosts involve tight regulation of gene expression, mainly post-transcriptionally. Nevertheless, chromatin structure/organization of trypanosomatids is similar to other eukaryotes, including histone variants and post-translational modifications...
January 11, 2017: Journal of Proteome Research
https://www.readbyqxmd.com/read/28075602/enantioselective-hydrophosphonylation-of-in-situ-generated-n-acyl-ketimines-catalyzed-by-binol-derived-phosphoric-acid
#8
Arun Suneja, Rajshekhar A Unhale, Vinod K Singh
An efficient route to pharmacologically interesting isoindolinone-based α-amino phosphonates is described via asymmetric hydrophosphonylation of in situ generated ketimines catalyzed by BINOL-derived phosphoric acid. The reaction proceeds smoothly at ambient temperature affording a variety of α-amino phosphonates with a quaternary stereogenic center embedded in isoindolinone motif in high yields with excellent enantiomeric ratios (up to 98.5:1.5 er). Several interesting transformations of the products into valuable synthetic intermediates are also depicted...
January 11, 2017: Organic Letters
https://www.readbyqxmd.com/read/28073163/hydrocarbon-stapled-lipopeptides-exhibit-selective-antimicrobial-activity
#9
Zachary B Jenner, Christopher M Crittenden, Martín Gonzalez, Jennifer S Brodbelt, Kerry A Bruns
Antimicrobial peptides (AMPs) occur widely in nature and have been studied for their therapeutic potential. AMPs are of interest due to the large number of possible chemical structural combinations using natural and unnatural amino acids, with varying effects on their biological activities. Using physicochemical properties from known naturally occurring amphipathic cationic AMPs, several hydrocarbon-stapled lipopeptides (HSLPs) were designed, synthesized, and tested for antimicrobial properties. Peptides were chemically modified by N-terminal acylation, C-terminal amidation, and some were hydrocarbon stapled by intramolecular olefin metathesis...
January 10, 2017: Biopolymers
https://www.readbyqxmd.com/read/28070495/an-atypical-presentation-of-acad9-deficiency-diagnosis-by-whole-exome-sequencing-broadens-the-phenotypic-spectrum-and-alters-treatment-approach
#10
H K Aintablian, V Narayanan, N Belnap, K Ramsey, T A Grebe
Acyl-CoA dehydrogenase 9 (ACAD9), linked to chromosome 3q21.3, is one of a family of multimeric mitochondrial flavoenzymes that catalyze the degradation of fatty acyl-CoA from the carnitine shuttle via β-oxidation (He et al. 2007). ACAD9, specifically, is implicated in the processing of palmitoyl-CoA and long-chain unsaturated substrates, but unlike other acyl-CoA dehydrogenases (ACADs), it has a significant role in mitochondrial complex I assembly (Nouws et al. 2010 & 2014). Mutations in this enzyme typically cause mitochondrial complex I deficiency, as well as a mild defect in long chain fatty acid metabolism (Haack et al...
March 2017: Molecular Genetics and Metabolism Reports
https://www.readbyqxmd.com/read/28070221/nannochloropsis-a-rich-source-of-diacylglycerol-acyltransferases-for-engineering-of-triacylglycerol-content-in-different-hosts
#11
Krzysztof Zienkiewicz, Agnieszka Zienkiewicz, Eric Poliner, Zhi-Yan Du, Katharina Vollheyde, Cornelia Herrfurth, Sofia Marmon, Eva M Farré, Ivo Feussner, Christoph Benning
BACKGROUND: Photosynthetic microalgae are considered a viable and sustainable resource for biofuel feedstocks, because they can produce higher biomass per land area than plants and can be grown on non-arable land. Among many microalgae considered for biofuel production, Nannochloropsis oceanica (CCMP1779) is particularly promising, because following nutrient deprivation it produces very high amounts of triacylglycerols (TAG). The committed step in TAG synthesis is catalyzed by acyl-CoA:diacylglycerol acyltransferase (DGAT)...
2017: Biotechnology for Biofuels
https://www.readbyqxmd.com/read/28069688/up-regulation-of-cb2-receptors-in-reactive-astrocytes-in-canine-degenerative-myelopathy-a-disease-model-of-amyotrophic-lateral-sclerosis
#12
María Fernández-Trapero, Francisco Espejo-Porras, Carmen Rodríguez-Cueto, Joan R Coates, Carmen Pérez-Díaz, Eva de Lago, Javier Fernández-Ruiz
Targeting the CB2 receptor afforded neuroprotection in SOD1(G93A) mutant mice, a model of amyotrophic lateral sclerosis (ALS). The neuroprotective effects of CB2 receptors were facilitated by their up-regulation in the spinal cord in SOD1(G93A) mutant mice. Herein, we have investigated whether a similar CB2 receptor up-regulation, as well as parallel changes in other endocannabinoid elements, are evident in the spinal cord of dogs with degenerative myelopathy (DM), caused from mutations in the superoxide dismutase 1 gene (SOD1)...
January 9, 2017: Disease Models & Mechanisms
https://www.readbyqxmd.com/read/28069670/the-acyl-desaturase-cer17-is-involved-in-producing-wax-unsaturated-primary-alcohols-and-cutin-monomers
#13
Xianpeng Yang, Huayan Zhao, Dylan K Kosma, Pernell Tomasi, John M Dyer, Rong-Jun Li, Xiulin Liu, Zhouya Wang, Eugene P Parsons, Matthew A Jenks, Shiyou Lu
We report n-6 monounsaturated primary alcohols (C26:1, C28:1, and C30:1 homologues) in the cuticular waxes of Arabidopsis inflorescence stem, a class of wax not previously reported in Arabidopsis. The Arabidopsis cer17 mutant was completely deficient in these monounsaturated alcohols, and CER17 was found to encode a predicted ACYL-COENZYME A DESATURASE LIKE4 (ADS4). Studies of the Arabidopsis cer4 mutant, and yeast variously expressing CER4 (a predicted fatty acyl-CoA reductase) with CER17/ADS4, demonstrated CER4's principal role in synthesis of these monounsaturated alcohols...
January 9, 2017: Plant Physiology
https://www.readbyqxmd.com/read/28069651/inhibition-by-avibactam-and-clavulanate-of-the-%C3%AE-lactamases-kpc-2-and-ctx-m-15-harboring-the-substitution-n132g-in-the-conserved-motif-sdn
#14
Clément Ourghanlian, Daria Soroka, Michel Arthur
The substitution N(132)G in the motif SDN of class A β-lactamases from rapidly-growing mycobacteria was previously shown to impair their inhibition by avibactam but to improve the stability of acyl-enzymes formed with clavulanate. The same substitution was introduced in KPC-2 and CTX-M-15 to assess its impact on β-lactamases from Enterobacteriaceae and evaluate whether it could lead to resistance to the ceftazidime-avibactam combination. Kinetic parameters for the inhibition of the β-lactamases by avibactam and clavulanate were determined by spectrophotometry using nitrocefin as the substrate...
January 9, 2017: Antimicrobial Agents and Chemotherapy
https://www.readbyqxmd.com/read/28060484/a-highly-promiscuous-%C3%A3-ketoacyl-acp-synthase-kas-iii-like-protein-is-involved-in-pactamycin-biosynthesis
#15
Mostafa E Abugrain, Corey J Brumsted, Andrew R Osborn, Benjamin Philmus, Taifo Mahmud
β-Ketoacyl-acyl carrier protein (β-Ketoacyl-ACP) synthase (KAS) III catalyzes the first step in fatty acid biosynthesis, involving a Claisen condensation of the acetyl-CoA starter unit with the first extender unit, malonyl-ACP, to form acetoacetyl-ACP. KAS III-like proteins have also been reported to catalyze acyltransferase reactions using coenzyme A esters or discrete ACP-bound substrates. Here, we report the in vivo and in vitro characterizations of a KAS III-like protein (PtmR), which directly transfers a 6-methylsalicylyl moiety from an iterative type I polyketide synthase to an aminocyclopentitol unit in pactamycin biosynthesis...
January 12, 2017: ACS Chemical Biology
https://www.readbyqxmd.com/read/28059521/conformational-entropy-from-nmr-relaxation-in-proteins-the-srls-perspective
#16
Oren Tchaicheeyan, Eva Meirovitch
Conformational entropy changes associated with bond-vector motions in proteins contribute to the free energy of ligand binding. To derive such contributions we apply the slowly relaxing local structure (SRLS) approach to NMR relaxation from (15)N-H bonds or C-CDH2 moieties of several proteins in free and ligand-bound form. The spatial restraints on probe motion, which determine the extent of local order, are expressed in SRLS by a potential, u(θ). The latter yields the orientational probability density, Peq = exp(-u(θ)), hence the related conformational entropy, Š=-∫Peq(θ) ln⁡[Peq(<it>θ</it>)]sin<it>⁡θ</it> d<it>θ</it> (Š is "entropy" in units of kBT, and θ represents the bond-vector orientation in the protein)...
January 6, 2017: Journal of Physical Chemistry. B
https://www.readbyqxmd.com/read/28057571/acyl-chain-preference-and-inhibitor-identification-of-moraxella-catarrhalis-lpxa-insight-through-crystal-structure-and-computational-studies
#17
Shivendra Pratap, Pooja Kesari, Ravi Yadav, Aditya Dev, Manju Narwal, Pravindra Kumar
Lipopolysaccharide (LPS) is an important surface component and a potential virulence factor in the pathogenesis of Gram-negative bacteria. UDP-N-acetylglucosamine acyltransferase (LpxA) enzyme catalyzes the first reaction of LPS biosynthesis, reversible transfer of R-3-hydroxy-acyl moiety from donor R-3-hydroxy-acyl-acyl carrier protein to the 3' hydroxyl position of UDP-N-acetyl-glucosamine. LpxA enzyme's essentiality in bacterial survival and absence of any homologous protein in humans makes it a promising target for anti-bacterial drug development...
January 3, 2017: International Journal of Biological Macromolecules
https://www.readbyqxmd.com/read/28055957/analysis-of-molecular-mechanisms-of-5-fluorouracil-induced-steatosis-and-inflammation-in-vitro-and-in-mice
#18
Judith Sommer, Abdo Mahli, Kim Freese, Tobias S Schiergens, Fulya Suzan Kuecuekoktay, Andreas Teufel, Wolfgang E Thasler, Martina Müller, Anja K Bosserhoff, Claus Hellerbrand
Chemotherapy-associated steatohepatitis is attracting increasing attention because it heralds an increased risk of morbidity and mortality in patients undergoing surgery because of liver metastases. The aim of this study was to develop in vitro and in vivo models to analyze the pathogenesis of 5-fluorouracil (5-FU)-induced steatohepatitis.Therefore, primary human hepatocytes and HepG2 hepatoma cells were incubated with 5-FU at non-toxic concentrations up to 24 h. Furthermore, hepatic tissue of C57BL/6N mice was analyzed 24 h after application of a single 5-FU dose (200 mg/kg body weight)...
December 30, 2016: Oncotarget
https://www.readbyqxmd.com/read/28049617/synthesis-of-antimicrobial-glucosamides-as-bacterial-quorum-sensing-mechanism-inhibitors
#19
Nripendra N Biswas, Tsz Tin Yu, Önder Kimyon, Shashidhar Nizalapur, Christopher R Gardner, Mike Manefield, Renate Griffith, David StC Black, Naresh Kumar
Bacteria communicate with one another and regulate their pathogenicity through a phenomenon known as quorum sensing (QS). When the bacterial colony reaches a threshold density, the QS system induces the production of virulence factors and the formation of biofilms, a powerful defence system against the host's immune responses. The glucosamine monomer has been shown to disrupt the bacterial QS system by inhibiting autoinducer (AI) signalling molecules such as the acyl-homoserine lactones (AHLs). In this study, the synthesis of acetoxy-glucosamides 8, hydroxy-glucosamides 9 and 3-oxo-glucosamides 12 was performed via the 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl) and N,N'-dicyclohexylcarbodiimide (DCC) coupling methods...
December 21, 2016: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28045445/asymmetric-total-syntheses-of-two-3-acyl-5-6-dihydro-2h-pyrones-r-podoblastin-s-and-r-lachnelluloic-acid-with-verification-of-the-absolute-configuration-of-lachnelluloic-acid
#20
Tetsuya Fujiwara, Takeshi Tsutsumi, Kohei Nakata, Hidefumi Nakatsuji, Yoo Tanabe
Expedient asymmetric total syntheses of both (R)-podoblastin-S and (R)-lachnelluloic acid, representative of natural 3-acyl-5,6-dihydro-2H-pyran-2-ones, were performed. Compared with the reported total synthesis of (R)-podoblastin-S (14 steps, overall 5% yield), the present study was achieved in only five steps in an overall 40% yield and with 98% ee (HPLC analysis). In a similar strategy, the first asymmetric total synthesis of the relevant (R)-lachnelluloic acid was achieved in an overall 40% yield with 98% ee (HPLC analysis)...
January 1, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
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