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N-acyl or endocannnabanoid or NAPE

Andrew G Palmer, Arijit Mukherjee, Danielle M Stacy, Stephen Lazar, Jean-Michel Ané, Helen E Blackwell
Density-dependent phenotypic switching in bacteria, the phenomenon of quorum sensing (QS), is instrumental in many pathogenic and mutualistic behaviors. In many Gram-negative bacteria, QS is regulated by N-acylated-l-homoserine lactones (AHLs). Synthetic analogues of these AHLs hold significant promise for regulating QS at the host-symbiont interface. Regulation depends on refined temporal and spatial models of quorums under native conditions. Critical to this is an understanding of how the presence of these signals may affect a prospective host...
October 14, 2016: Chembiochem: a European Journal of Chemical Biology
Stefania Brocca, Cristian Ferrari, Alberto Barbiroli, Alessandra Pesce, Marina Lotti, Marco Nardini
Life in cold environments requires an overall increase in the flexibility of macromolecular and supramolecular structures to allow biological processes to take place at low temperature. Conformational flexibility supports high catalytic rates of enzymes in the cold but in several cases is also a cause of instability. The three-dimensional structure of the psychrophilic acyl aminoacyl peptidase from Sporosarcina psychrophila (SpAAP) reported in this paper highlights adaptive molecular changes resulting in a fine-tuned trade-off between flexibility and stability...
October 14, 2016: FEBS Journal
Takuya Kaji, Motoki Murai, Hiroaki Itoh, Jyunichiro Yasukawa, Hiroshi Hamamoto, Kazuhisa Sekimizu, Masayuki Inoue
Lysocin E (1) is a structurally complex 37-membered depsipeptide comprising 12 amino-acid residues with an N-methylated amide and an ester linkage. Compound 1 binds to menaquinone (MK) in the bacterial membrane to exert its potent bactericidal activity. To decipher the biologically important functionalities within this unique antibiotic, we performed a comprehensive structure-activity relationship (SAR) study by systematically changing the side-chain structures of l-Thr-1, d-Arg-2, N-Me-d-Phe-5, d-Arg-7, l-Glu-8, and d-Trp-10...
October 14, 2016: Chemistry: a European Journal
Jennifer Popko, Cornelia Herrfurth, Kirstin Feussner, Till Ischebeck, Tim Iven, Richard Haslam, Mary Hamilton, Olga Sayanova, Jonathan Napier, Inna Khozin-Goldberg, Ivo Feussner
Oleaginous microalgae are considered as a promising resource for the production of biofuels. Especially diatoms arouse interest as biofuel producers since they are most productive in carbon fixation and very flexible to environmental changes in the nature. Naturally, triacylglycerol (TAG) accumulation in algae only occurs under stress conditions like nitrogen-limitation. We focused on Phaeodactylum strain Pt4 (UTEX 646), because of its ability to grow in medium with low salinity and therefore being suited when saline water is less available or for wastewater cultivation strategies...
2016: PloS One
F G Dupuy, S P Fernández Bordín, B Maggio, R G Oliveira
Ceramides constitute a group of lipids with usually high melting temperature that also favor negative curvature in membranes when mixed with other lipids. The short chain C10:0 ceramide is an asymmetric lipid which consists of an 18 carbon sphingosine base N-acylated with decanoic acid. According to high sensitivity differential scanning calorimetry, it shows a minor exothermic peak at 61°C and a main endothermic transition at 75°C. By small angle X-ray scattering and polarized light microscopy we found that, at temperatures below the main transition, the fully hydrated lipid dispersions are arranged in a tridimensional structure corresponding to an inverted hexagonal phase...
October 5, 2016: Colloids and Surfaces. B, Biointerfaces
Efrat Gottlieb-Abraham, Orit Gutman, Govind M Pai, Ignacio Rubio, Yoav I Henis
The interactions of Src family kinases (SFKs) with the plasma membrane are crucial for their activity. They depend on their fatty-acylated N-termini, containing N-myristate and either a polybasic cluster (in Src) or palmitoylation sites (e.g., Fyn). To investigate the roles of these moieties in SFK membrane association, we employed FRAP beam-size analysis to study the membrane interactions of c-Src-GFP or Fyn-GFP fatty-acylation mutants. Our studies showed for the first time that the membrane association of Fyn is more stable than that of Src, an effect lost in a Fyn mutant lacking the palmitoylation sites...
October 12, 2016: Molecular Biology of the Cell
Aaron W Tang, Xianqi Kong, Victor Terskikh, Gang Wu
We report preparation, trapping, and solid-state 17O NMR characterization of three unstable acyl-enzyme intermediates (≈ 26 kDa): p-N,N-dimethylamino-[17O]benzoyl-chymotrypsin, trans-o-methoxy-[17O]cinnamoyl-chymotrypsin, and trans-p-methoxy-[17O]cinnamoyl-chymotrypsin. We show that both the 17O chemical shifts and nuclear quadrupolar parameters obtained for these acyl-enzyme intermediates in the solid state are correlated with their deacylation rate constants measured in aqueous solution. With the aid of quantum mechanical calculations, the experimental 17O NMR parameters were interpreted as to reflect the hydrogen bonding interactions between the carbonyl (C=17O) functional group of the acyl moiety and the two NH groups from the protein backbone (Ser195 and Gly193) in the oxyanion hole, a general feature of all serine proteases...
October 12, 2016: Journal of Physical Chemistry. B
Tomoko Abe, Yoshiteru Hashimoto, Sayaka Sugimoto, Kenta Kobayashi, Takuto Kumano, Michihiko Kobayashi
The adenylation domain of nonribosomal peptide synthetase (NRPS) is responsible for the selective substrate recognition and its activation (as an acyl-O-AMP intermediate) during ATP consumption. DhbE, a stand-alone adenylation domain, acts on an aromatic acid, 2,3-dihydroxybenzoic acid (DHB). This activation is the initial step of the synthesis of bacillibactin that is a high-affinity small-molecule iron chelator also termed siderophore. Subsequently, the activated DHB is transferred and attached covalently to a peptidyl carrier protein domain via a thioester bond...
October 12, 2016: Journal of Antibiotics
Richard C Brewster, Georgina C Gavins, Barbara Günthardt, Sarah Farr, Kimberly M Webb, Philipp Voigt, Alison N Hulme
Rapid, site-selective modification of cysteine residues with chloromethyl-triazole derivatives generates pseudo-acyl sLys motifs, mimicking important post-translational modifications. Near-native biotinylation of peptide and protein substrates is shown to be site-selective and modified histone H4 retains functional activity.
October 6, 2016: Chemical Communications: Chem Comm
Noriko Takahashi, Toshihiro Ohba, Masahiko Imai, Shinya Hasegawa, Katsuhiko Takahashi, Masahiro Yamasaki, Yuri Kameoka
Retinoic acid (RA) has a variety of biological effects in mammalian cells and tissues. It is well known that RA induces differentiation of human acute promyelocytic leukemia (APL) HL60 cells, fresh human APL cells, and clinical remission in patients with APL. Retinoylation (acylation of proteins by RA) is a possible pathway for RA action. However, an understanding of the role that retinoylation plays in the actions of RA is lacking. In the current study, several retinoylated proteins were detected in RA-treated HL60 fractions following Mono Q anion exchange chromatography and analysis using two-dimensional polyacrylamide gel electrophoresis...
October 6, 2016: Biochimica et Biophysica Acta
Miriam Payá-Milans, Jose Antonio Aznar-Moreno, Tiago S Balbuena, Richard P Haslam, Satinder K Gidda, Javier Pérez-Hormaeche, Robert T Mullen, Jay J Thelen, Johnathan A Napier, Joaquín J Salas, Rafael Garcés, Enrique Martínez-Force, Mónica Venegas-Calerón
In oil crops, triacylglycerol biosynthesis is an important metabolic pathway in which glycerol-3-phosphate acyltransferase (GPAT) performs the first acylation step. Mass spectrometry analysis of developing sunflower (Helianthus annuus) seed membrane fractions identified an abundant GPAT, HaGPAT9 isoform 1, with a N-terminal peptide that possessed two phosphorylated residues with possible regulatory function. HaGPAT9-1 belongs to a broad eukaryotic GPAT family, similar to mammalian GPAT3, and it represents one of the two sunflower GPAT9 isoforms, sharing 90% identity with HaGPAT9-2...
November 2016: Plant Science: An International Journal of Experimental Plant Biology
Niharika Singh, Amrita Patil, Asmita Prabhune, Mamta Raghav, Gunjan Goel
The present study investigates the role of quorum sensing (QS) molecules expressed by C. sakazakii in biofilm formation and extracellular polysaccharide expression. The QS signaling was detected using Chromobacterium violaceum 026 and Agrobacterium tumefaciens NTL4(pZLR4) based bioassay. Long chain N-acyl-homoserine lactones (AHLs) with C6- C18 chain length were identified using High Performance Liquid Chromatography and Liquid Chromatography-High Resolution Mass Spectrometry. A higher Specific Biofilm Formation (SBF) index (p < 0...
October 7, 2016: Virulence
Sergey M Shishlyannikov, Alyona A Nikonova, Igor V Klimenkov, Alexander G Gorshkov
The accumulation of hydrophobic compounds by phytoplankton plays a crucial role in the biogeochemical cycle of persistent organic pollutants (POPs) in aquatic environments. We studied the accumulation of polycyclic aromatic hydrocarbons (PAHs) in the freshwater diatom Synedra acus subsp. radians during its cultivation with crude oil hydrocarbons, using epifluorescent and laser confocal microscopy as well as gas chromatography-mass spectrometry (GC/MS) analysis. Our results revealed that in the presence of crude oil or an extract of a crude oil/n-hexane solution (light oil), S...
October 6, 2016: Environmental Science and Pollution Research International
Teresa F Vaughan, John L Spencer
The synthesis and coordination behaviour of the pyridylphosphine ligand o-C6H4(CH2PPy2)2 (Py = 2-pyridyl) are reported. The phosphine selenide was synthesised and the (1)JPSe value of 738 Hz indicates the phosphorus atoms have a similar basicity to PPh3. The ligand reacts with platinum(ii) and palladium(ii) complexes to give simple diphosphine complexes of the type [MX2(PP)] (M = Pt, X = Cl, I, Me, Et; M = Pd, X = Cl, Me). When the ligand is reacted with chloromethyl(hexa-1,5-diene)platinum the [PtClMe(PP)] complex results, from which a series of unsymmetrical platinum complexes of the type [PtMeL(PP)](+) (L = PPh3, PTA, SEt2 and pyridine) can be made...
September 28, 2016: Dalton Transactions: An International Journal of Inorganic Chemistry
Dominika Załubiniak, Maciej Zakrzewski, Piotr Piątek
Compounds 2 and 3 were designed and prepared as heteroditopic ion-pair receptors. The design features a 2,2-bis(aminomethyl)propionic acid core to connect and pre-organize binding groups. The cation binding is provided by a sodium selective N-acyl aza-18-crown-6 subunit whereas for anion complexation, two urea groups (receptor 2) or two squaramide groups (receptor 3) were introduced. Beyond acting as anion binding sites, the urea and squaramide groups were used to support sodium cation complexation through metal carbonyl oxygen lone pair interactions...
October 4, 2016: Dalton Transactions: An International Journal of Inorganic Chemistry
Nishaben M Patel, Joseph D Moore, Helen E Blackwell, Daniel Amador-Noguez
N-acyl L-homoserine lactones (AHLs) constitute a predominant class of quorum-sensing signaling molecules used by Gram-negative bacteria. Here, we report a sensitive and non-targeted HPLC-MS/MS method based on parallel reaction monitoring (PRM) to identify and quantitate known, unanticipated, and novel AHLs in microbial samples. Using a hybrid quadrupole-high resolution mass analyzer, this method integrates MS scans and all-ion fragmentation MS/MS scans to allow simultaneous detection of AHL parent-ion masses and generation of full mass spectra at high resolution and high mass accuracy in a single chromatographic run...
2016: PloS One
Sébastien Goudedranche, Céline Besnard, Léo Egger, Jérôme Lacour
N-aryl γ-lactams react intermolecularly with acceptor-acceptor diazo reagents, usually dicarbonyl compounds, in a copper-catalyzed process to yield functionalized pyrrolidines with α-pseudoquaternary centers. As 1,2-acyl or -phosphoryl migration is preferred, single regioisomers are obtained. Furthermore, in the presence of a Lewis acid, subsequent Friedel-Crafts reactions yield tricyclic pyrrolizidines in excellent yields (90-96 %) and diastereoselectivities (up to >20:1).
October 4, 2016: Angewandte Chemie
Javier Raya-González, Crisanto Velázquez-Becerra, Salvador Barrera-Ortiz, José López-Bucio, Eduardo Valencia-Cantero
Plant growth-promoting rhizobacteria are natural inhabitants of roots, colonize diverse monocot and dicot species, and affect several functional traits such as root architecture, adaptation to adverse environments, and protect plants from pathogens. N,N-dimethyl-hexadecylamine (C16-DMA) is a rhizobacterial amino lipid that modulates the postembryonic development of several plants, likely as part of volatile blends. In this work, we evaluated the bioactivity of C16-DMA and other related N,N-dimethyl-amines with varied length and found that inhibition of primary root growth was related to the length of the acyl chain...
September 30, 2016: Protoplasma
Diego Romano Perinelli, Marco Cespi, Luca Casettari, Driton Vllasaliu, Michela Cangiotti, Maria Francesca Ottaviani, Gianfabio Giorgioni, Giulia Bonacucina, Giovanni Filippo Palmieri
Toxicity is one of the main concern limiting the use of surfactants. Many efforts have been devoted to the development of new amphiphilic molecules characterized by a lower toxicological profile and environmental impact. N-acyl amino acids are a class of anionic surfactants that can find applications in different technological fields as an alternative to sulphate-based surfactants (e.g., sodium dodecyl sulphate). The understanding of the relationship between chemical structure and toxicological profile is fundamental for the disclosure of the full potential of these amphiphiles...
September 28, 2016: European Journal of Pharmaceutics and Biopharmaceutics
Jakob Franke, Christian Hertweck
Thioesters play essential roles in many biosynthetic pathways to fatty acids, esters, polyketides, and non-ribosomal peptides. Coenzyme A (CoA) and related phosphopantetheine thioesters are typically employed as activated acyl units for diverse C-C, C-O, and C-N coupling reactions. To study and control these enzymatic assembly lines in vitro and in vivo structurally simplified analogs such as N-acetylcysteamine (NAC) thioesters have been developed. This review gives an overview on experimental strategies enabled by synthetic NAC thioesters, such as the elucidation of complex biosynthetic pathways and enzyme mechanisms as well as precursor-directed biosynthesis and mutasynthesis...
September 28, 2016: Cell Chemical Biology
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