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D Marian Szebenyi, Irina Kriksunov, Kevin J Howe, John S Ramsey, David G Hall, Michelle L Heck, Stuart B Krasnoff
The title compound C22 H39 NO9 ·CH3 OH [systematic name: ( S )- N -(( S )-{(2 S ,4 R ,6 R )-6-[( S )-2,3-di-hydroxy-prop-yl]-4-hy-droxy-5,5-di-methyl-tetra-hydro-2 H -pyran-2-yl}(hy-droxy)meth-yl)-2-hy-droxy-2-[(2 R ,5 R ,6 R )-2-meth-oxy-5,6-dimeth-yl-4-methyl-ene-tetra-hydro-2 H -pyran-2-yl]acetamide methanol monosolvate], was isolated from the Asian citrus psyllid, Diaphorina citri Kuwayama, and crystallizes in the space group P 21 . ' Candidatus Profftella armatura' a bacterial endosymbiont of D. citri , biosynthesizes diaphorin, which is a hybrid polyketide-nonribosomal peptide comprising two highly substituted tetra-hydro-pyran rings joined by an N -acyl aminal bridge [Nakabachi et al...
April 1, 2018: Acta Crystallographica. Section E, Crystallographic Communications
Tomonori Tamura, Tsuyoshi Ueda, Taiki Goto, Taku Tsukidate, Yonatan Shapira, Yuki Nishikawa, Alma Fujisawa, Itaru Hamachi
Selective modification of native proteins in live cells is one of the central challenges in recent chemical biology. As a unique bioorthogonal approach, ligand-directed chemistry recently emerged, but the slow kinetics limits its scope. Here we successfully overcome this obstacle using N-acyl-N-alkyl sulfonamide as a reactive group. Quantitative kinetic analyses reveal that ligand-directed N-acyl-N-alkyl sulfonamide chemistry allows for rapid modification of a lysine residue proximal to the ligand binding site of a target protein, with a rate constant of ~104  M-1  s-1 , comparable to the fastest bioorthogonal chemistry...
May 14, 2018: Nature Communications
Putri D Utari, Rita Setroikromo, Barbro N Melgert, Wim J Quax
Pseudomonas aeruginosa is the predominant pathogen in pulmonary infections associated with cystic fibrosis. Quorum sensing (QS) systems regulate the production of virulence factors and play an important role in the establishment of successful P. aeruginosa infections. Inhibition of the QS system (termed quorum quenching) renders the bacteria avirulent thus serving as an alternative approach in the development of novel antibiotics. Quorum quenching in Gram negative bacteria can be achieved by preventing the accumulation of N -acyl homoserine lactone (AHL) signaling molecule via enzymatic degradation...
2018: Frontiers in Cellular and Infection Microbiology
Yu Luo, Muhammad Afzal Javed, Harry Deneer, Xialu Chen
Bacteria inhabit a vast range of biological niches and have evolved diverse mechanisms to cope with environmental stressors. The genus Acinetobacter comprises a complex group of Gram-negative bacteria. Some of these bacteria such as A. baumannii are nosocomial pathogens. They are often resistant to multiple antibiotics and are associated with epidemic outbreaks. A. radioresistens is generally considered to be a commensal bacterium on human skin or an opportunistic pathogen. Interestingly, this species has exceptional resistance to a range of environmental challenges which contributes to its persistence in clinical environment and on human skin...
May 10, 2018: Scientific Reports
Goki Hirata, Hiromitsu Maeda
The abilities of dipyrrolyldiketone boron complexes as hydrogen-bonding donor organocatalysts were examined by the Mannich-type reaction of N-acyl heteroarenium chlorides with 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene, as well as by the classical N-alkylation of amines with trityl chloride under base-free conditions. 1 H NMR examinations of the hydrogen-bonding interaction between the pyrrole NH of the catalyst and the Cl- in the N-acyl heteroarenium salt suggested that the activation of N-acyl heteroarenium chlorides occurs through anion binding by the catalyst...
May 8, 2018: Organic Letters
Basmah Almohaywi, Aditi Taunk, Daniel S Wenholz, Shashidhar Nizalapur, Nripendra N Biswas, Kitty K K Ho, Scott A Rice, George Iskander, David StC Black, Renate Griffith, Naresh Kumar
Bacterial infections, particularly hospital-acquired infections caused by Pseudomonas aeruginosa , have become a global threat with a high mortality rate. Gram-negative bacteria including P. aeruginosa employ N -acyl homoserine lactones (AHLs) as chemical signals to regulate the expression of pathogenic phenotypes through a mechanism called quorum sensing (QS). Recently, strategies targeting bacterial behaviour or QS have received great attention due to their ability to disarm rather than kill pathogenic bacteria, which lowers the evolutionary burden on bacteria and the risk of resistance development...
May 7, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Elk Kossatz, Daniel Silva-Peña, Juan Suárez, Fernando R de Fonseca, Rafael Maldonado, Patricia Robledo
The PPAR-α agonist, oleoylethanolamide (OEA) has neuroprotective properties in stroke models. However, its rapid degradation represents a limitation for an effective therapeutic approach. In this study, we evaluated the effects of a stable OEA-modeled compound, octadecylpropyl sulfamide (SUL) on the cognitive, behavioral, cellular and molecular alterations associated with hypoxia-ischemia (HI) in mice. Mice subjected to HI were treated with the PPAR-α antagonist GW6471 (GW) (1 mg/kg) followed 15 min later by SUL (3 and 10 mg/kg)...
2018: Frontiers in Pharmacology
Kibaek Lee, Yea-Won Kim, Seonki Lee, Sang Hyun Lee, Chang Hyun Nahm, Hyeokpil Kwon, Pyung-Kyu Park, Kwang-Ho Choo, Ismail Koyuncu, Anja Drews, Chung-Hak Lee, Jung-Kee Lee
Bacterial quorum quenching (QQ) by means of degrading signaling molecules has been applied to anti-biofouling strategy in a membrane bioreactor (MBR) for wastewater treatment. However, the target signaling molecules have been limited to N-acyl homoserine lactones participating in intra-species quorum sensing. Here, an approach to disrupt autoinducer-2 (AI-2) signaling molecules participating in inter-species quorum sensing, was pursued as a next-generation anti-biofouling strategy in an MBR for wastewater treatment...
May 1, 2018: Environmental Science & Technology
Yukitoshi Nagahara, Kei Kawakami, Abudubari Sikandan, Daiki Yagi, Ryo Nishikawa, Takahisa Shinomiya
Sphingolipids are putative intracellular signal mediators in cell differentiation, growth inhibition, and apoptosis. Especially, sphingoid base-backbones of sphingolipids (sphingosine, sphinganine, and phytosphingosine) and their metabolites N-acyl-sphingoid bases (ceramides) are highly bioactive. In skin, one of the caspases, caspase-14, is expressed predominantly in cornifying epithelia, and caspase-14 plays an important role in keratinocyte differentiation. As ceramides were surrounding lipids in the keratinocytes and ceramides stimulate keratinocyte differentiation, we therefore examined the upregulation of caspase-14 by various sphingoid bases and ceramide...
2018: Biological & Pharmaceutical Bulletin
Tomáš Řezanka, Milada Vítová, Jaromír Lukavský, Karel Sigler
Freshwater bryozoan Pectinatella magnifica was collected from a sand pit (South Bohemia). The total lipids after extraction from lyophilized bryozoans were analyzed using high-performance liquid chromatography/high-resolution negative tandem electrospray mass spectrometry. A total of 19 lipid classes were identified, including N-acyl-substituted phospholipids, that is, N-acylphosphatidylethanolamine and N-acylphosphatidylserine in their plasmenyl forms. Based on gas chromatography/mass spectrometry of 3-pyridylcarbonyl (picolinyl) esters, a very unusual fatty acid was identified, namely 24:7n-3 (all-cis-3,6,9,12,15,18,21-tetracosaheptaenoic acid)...
April 30, 2018: Lipids
Bing Zhang, Piet N L Lens, Wenxin Shi, Ruijun Zhang, Zhiqiang Zhang, Yuan Guo, Xian Bao, Fuyi Cui
Bacteria and algae often coexist in the aerobic granular sludge (AGS) system in a photo-bioreactor, forming algal-bacterial granular sludge. In this study, the physicochemical characteristics and microbial attachment potential of the AGS and algal-bacterial granular sludge were comparatively analyzed. Results clearly showed that the larger and denser algal-bacterial granular sludge had stronger attachment potential compared to the AGS (as the control). A bioassay with Agrobacterium tumefaciens KYC55 indicated that N-acyl-homoserine lactones (AHLs) existed in both sludge types, but further investigations revealed that the relative AHL content of the algal-bacterial granular sludge obviously increased and slightly decreased during phases II and III, respectively, but was consistently higher than the AGS...
April 25, 2018: Applied Microbiology and Biotechnology
Somayeh Torabi Delshad, Siyavash Soltanian, Hassan Sharifiyazdi, Masoud Haghkhah, Peter Bossier
AIMS: A variety of pathogens use quorum sensing (QS) to control the expression of their virulence factors. QS interference has hence been proposed as a promising anti-virulence strategy. The specific aim of this study was to isolate bacteria from trout tissue able to degrade N-Acyl Homoserine Lactones (AHL), a QS molecule family. METHODS AND RESULTS: In total 132 isolates were screened for AHL degradation using Chromobacterium violaceum CV026 as a biosensor. Twenty four quorum quenching (QQ) isolates were identified biochemically and characterized using 16S rDNA sequencing...
April 25, 2018: Journal of Applied Microbiology
Mauro Pascolutti, Larissa Dirr, Patrice Guillon, Annelies Van Den Bergh, Thomas Ve, Robin J Thomson, Mark von Itzstein
A novel approach to human parainfluenza virus type-3 (hPIV-3) inhibitor design has been evaluated by targeting an unexplored pocket within the active site region of the virus' haemagglutinin-neuraminidase (HN) that is normally occluded upon ligand engagement. To explore this opportunity, we developed a highly efficient route to introduce nitrogen-based functionalities at the naturally unsubstituted C-3 position on the neuraminidase inhibitor template N-acyl-2,3-dehydro-2-deoxy-neuraminic acid (N-acyl-Neu2en), via a regioselective 2,3-bromoazidation...
April 25, 2018: ACS Chemical Biology
Jade L Ronan, Nadia Kadi, Stephen A McMahon, James H Naismith, Lona M Alkhalaf, Gregory L Challis
Hydroxamate groups play key roles in the biological function of diverse natural products. Important examples include trichostatin A, which inhibits histone deacetylases via coordination of the active site zinc(II) ion with a hydroxamate group, and the desferrioxamines, which use three hydroxamate groups to chelate ferric iron. Desferrioxamine biosynthesis in Streptomyces species involves the DesD-catalysed condensation of various N -acylated derivatives of N -hydroxycadaverine with two molecules of N -succinyl- N -hydroxycadaverine to form a range of linear and macrocyclic tris-hydroxamates...
June 5, 2018: Philosophical Transactions of the Royal Society of London. Series B, Biological Sciences
Yinglu Wang, Lin Han, Ning Yuan, Hanxuan Wang, Hongxing Li, Jinrong Liu, Huan Chen, Qiang Zhang, Suwei Dong
Peptidyl thioesters or their surrogates with C-terminal β-branched hydrophobic amino acid residues usually exhibit poor reactivities in ligation reactions. Thus, activation using exogenous additives is required to ensure an acceptable reaction efficiency. Herein, we report a traceless ligation at Val-Xaa sites under mild thiol additive-free reaction conditions, whereby the introduction of β-mercaptan on the C-terminal valine residue effectively activates the otherwise unreactive N -acyl-benzimidazolinone (Nbz), and enables the use of a one-pot ligation-desulfurization strategy to generate the desired peptide products...
February 21, 2018: Chemical Science
Weiwei Dong, Jie Zhu, Xiang Guo, Delong Kong, Qi Zhang, Yiqing Zhou, Xiaoyang Liu, Shumiao Zhao, Zhiyong Ruan
N-Acyl homoserine lactones (AHLs) act as the key quorum sensing (QS) signal molecules in gram-negative bacteria, which coordinates gene expression and then activates various processes, including biofilm formation and production of virulence factors in some pathogens. Quorum quenching (QQ), which is the inactivation of the signal molecules by means of enzymatic degradation or modification, inhibits the processes of QS rather than killing the pathogens and is a promising antipathogenic strategy to control the bacterial pathogens...
April 16, 2018: Scientific Reports
Vidhyapriya Murugan, Krishnan Sankaran
In ELISA, a popular analytical diagnostic tool, the stable non-covalent immobilization (coating) of hydrophilic proteins/peptides on to hydrophobic polystyrene surface has remained a major common challenge. Recombinant bacterial lipid modification of proteins in Escherichia coli system has been shown in this study to solve this problem owing to the hydrophobic anchorage provided by three fatty acyl groups in N-acyl-S-diacylglyceryl Cys at the N-terminus. Exploiting this first post-translational protein engineering, the most abundantly expressed white spot syndrome viral protein ICP11 was lipid-modified and tested as a new target in a new ELISA method useful to shrimp farming...
April 14, 2018: Marine Biotechnology
Peiru Si, Shulian Liu, Dongxiao Tong, Meijin Cheng, Liwen Wang, Xiaoli Cheng
OBJECTIVE: To assess the association of polymorphisms of N-acyl-phosphatidylethanolamine-phospholipase D (DAPE-PLD) and fatty acid amide hydrolase (FAAH) genes, as well as their interaction, with schizophrenia. METHODS: Polymorphisms of NAPE-PLD rs12540583 and FAAH rs324420, rs2295633, and rs6429600 were determined with PCR - restriction fragment length polymorphism assay and Sanger sequencing. The genotypes of 345 subjects of Han Chinese origin diagnosed with schizophrenia and a 403 controls were compared...
April 10, 2018: Zhonghua Yi Xue Yi Chuan Xue za Zhi, Zhonghua Yixue Yichuanxue Zazhi, Chinese Journal of Medical Genetics
Farbod Salahi, Vatsal Purohit, Guillermo Ferraudi, Cynthia Stauffacher, Olaf Wiest, Paul Helquist
The synthesis of a new photocaged nicotinamide having an N-acyl carbamate linker and a p-hydroxyphenacyl (pHP) chromophore is described. The photophysical and photochemical studies showed an absorption maximum at λ = 330 nm and a quantum yield for release of 11% that are dependent upon both pH and solvent. While the acyl carbamate releases nicotinamide efficiently, a simpler amide linker was inert to photocleavage. This photocaged nicotinamide has significant advantages with respect to quantum yield, absorbance wavelength, rate of release, and solubility that make it the first practical example of a photocaged amide...
April 13, 2018: Organic Letters
E Gómez, S Carrocera, D Martin, P Herrero, N Canela, M Muñoz
Male and female early bovine embryos show dimorphic transcription that impacts metabolism. Individual release of metabolites was examined in a 24h single culture medium from Day-6 male and female morulae that developed to Day-7 expanded blastocysts. Embryos were produced in vitro, fertilized with a single bull and cultured in SOFaaci+6  g/L BSA. The embryonic sex was identified (amelogenin gene amplification). Embryos (N = 10 males and N = 10 females) and N = 6 blank samples (i.e. SOFaaci+6  g/L BSA incubated with no embryos) were collected from 3 replicates...
April 5, 2018: Theriogenology
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