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Phenylacetic acid

Mariana N Levandowski, Thiago C Rozada, Ulisses Z Melo, Ernani A Basso, Barbara C Fiorin
This paper presents a study on the conformational preferences of phenylacetic acid (PA) and its halogenated analogues (FPA, CPA, BPA). To clarify the effects that rule these molecules' behaviour, theoretical calculations were used, for both the isolated phase and solution, combined with nuclear magnetic resonance (NMR) and infrared (IR) spectroscopy. Most conformations of phenylacetic acid and its halogenated derivatives are stabilized through the hyperconjugative effect, which rules the conformational preference...
November 9, 2016: Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
Corey S Westfall, Ashley M Sherp, Chloe Zubieta, Sophie Alvarez, Evelyn Schraft, Romain Marcellin, Loren Ramirez, Joseph M Jez
In Arabidopsis thaliana, the acyl acid amido synthetase Gretchen Hagen 3.5 (AtGH3.5) conjugates both indole-3-acetic acid (IAA) and salicylic acid (SA) to modulate auxin and pathogen response pathways. To understand the molecular basis for the activity of AtGH3.5, we determined the X-ray crystal structure of the enzyme in complex with IAA and AMP. Biochemical analysis demonstrates that the substrate preference of AtGH3.5 is wider than originally described and includes the natural auxin phenylacetic acid (PAA) and the potential SA precursor benzoic acid (BA)...
November 29, 2016: Proceedings of the National Academy of Sciences of the United States of America
Jamiyan Purevsuren, Baasandai Bolormaa, Chogdon Narantsetseg, Renchindorj Batsolongo, Ochirbat Enkhchimeg, Munkhuu Bayalag, Yuki Hasegawa, Haruo Shintaku, SeijiYamaguchi
BACKGROUND: Inborn errors of metabolism (IEM) are rare genetic disorders in which a single gene defect causes a clinically significant block in a metabolic pathway. Clinical problems arise due to either accumulation of substrates that are toxic or interfere with normal function, or deficiency of the products that are used to synthesize essential compounds. There is no report of screening results or confirmed cases of IEM in Mongolia. Only pilot study of newborn screening for congenital hypothyroidism was implemented in Mongolia, where the incidence of congenital hypothyroidism is calculated to be 1:3057 in Mongolia...
December 2016: Molecular Genetics and Metabolism Reports
Sam D Cook, John J Ross
One of the fundamental plant growth substances, indole-3-acetic acid (IAA), belongs to a class of phytohormones known as auxins. The main IAA biosynthesis pathway involves the conversion of tryptophan to indole-3-pyruvic acid, which is in turn converted to IAA. The two enzymes responsible for these conversions, members of the TAA1 and YUCCA gene families, respectively, have recently been implicated in the synthesis of another auxin, phenylacetic acid (PAA). While there is some evidence to support this theory, there are also some concerns...
November 3, 2016: Plant Signaling & Behavior
Christiane Kiske, Svenja Noerenberg, Miriam Ecker, Xingyue Ma, Tohru Taniguchi, Kenji Monde, Wolfgang Eisenreich, Karl-Heinz Engel
The absolute configurations of chiral β-mercaptoalkanones had been previously assigned on the basis of the 1H NMR anisotropy method using (S)-2-methoxy-2-(1-naphthyl)propionic acid ((S)-MαNP) as chiral auxiliary. This study presents a reinvestigation of the configurations of 4-mercapto-2-pentanone, 1, 4-mercapto-2-heptanone, 2, and 2-mercapto-4-heptanone, 3. Enantiomers of 1, 2 and 3 were obtained by lipase-catalyzed hydrolyses of the respective acetylthioalkanones. Upon derivatization with (S)-MαNP, the configurations of the reaction products were deduced on the basis of the order of the HPLC-elution of the diastereoisomeric thioesters assuming that the sector rule previously developed for secondary alcohols is also valid for thiols...
October 25, 2016: Journal of Agricultural and Food Chemistry
A M Api, D Belsito, S Bhatia, M Bruze, P Calow, M L Dagli, W Dkant, A D Fryer, L Kromidas, S La Cava, J F Lalko, A Lapczynski, D C Liebler, T M Penning, V T Politano, G Ritacco, D Salvito, T W Schultz, J Shen, I G Sipes, B Wall, D K Wilcox
The use of this material under current conditions is supported by existing information. This material was evaluated for genotoxicity, repeated dose toxicity, developmental and reproductive toxicity, local respiratory toxicity, phototoxicity/photoallergenicity, skin sensitization, as well as environmental safety. Data show that this material is not genotoxic. Data from the suitable read across analog linalyl phenylacetate (CAS # 7143-69-3) show that this material does not have skin sensitization potential. The repeated dose toxicity endpoint was completed using linalyl cinnamate (CAS # 78-37-5) as a suitable read across analog, which provided a MOE > 100...
September 23, 2016: Food and Chemical Toxicology
Ali Gharibi Loron, Soroush Sardari, Jamshid Narenjkar, Mohammad Sayyah
BACKGROUND: Resistance to antiepileptic drugs as well as intolerability in 20-30% of the patients raises demand for developing new drugs with improved efficacy and safety. Acceptable anticonvulsant activity, good tolerability, and inexpensiveness of docosahexaenoic acid (DHA), make it as a good candidate for designing and development of the new anticonvulsant medications. METHODS: Ten DHA-based molecules were screened based on in silico screening of DHA-like molecules by root-mean-square deviation of atomic positions, biological activity score of Professional Association for SQL Server and structural requirements suggested by pharmacophore design...
September 4, 2016: Iranian Biomedical Journal
Hua Fang, Tianheng Xu, Duantao Cao, Longyin Cheng, Yunlong Yu
A novel bacterium capable of utilizing metamitron as the sole source of carbon and energy was isolated from contaminated soil and identified as Rhodococcus sp. MET based on its morphological characteristics, BIOLOG GP2 microplate profile, and 16S rDNA phylogeny. Genome sequencing and functional annotation of the isolate MET showed a 6,340,880 bp genome with a 62.47% GC content and 5,987 protein-coding genes. In total, 5,907 genes were annotated with the COG, GO, KEGG, Pfam, Swiss-Prot, TrEMBL, and nr databases...
2016: Scientific Reports
Fumihiro Ishikawa, Masato Shirahashi, Hiroshi Hayakawa, Asako Yamaguchi, Takatsugu Hirokawa, Takeshi Tsumuraya, Ikuo Fujii
Taking advantage of antibody molecules to generate tailor-made binding sites, we propose a new class of protein modifications, termed as "site-directed chemical mutation." In this modification, chemically synthesized catalytic components with a variety of steric and electronic properties can be noncovalently and nongenetically incorporated into specific sites in antibody molecules to induce enzymatic activity. Two catalytic antibodies, 25E2 and 27C1, possess antigen-combining sites which bind catalytic components and act as apoproteins in catalytic reactions...
October 21, 2016: ACS Chemical Biology
Jihyun Lee, Bronte Lee Shan Chan, Alyson E Mitchell
Free and bound phenolic acids were measured in the pulp and peel of four varieties of apples using high resolution mass spectrometry. Twenty-five phenolic acids were identified and included: 8 hydroxybenzoic acids, 11 hydroxycinnamic acids, 5 hydroxyphenylacetic acids, and 1 hydoxyphenylpropanoic acid. Several phenolics are tentatively identified for the first time in apples and include: methyl gallate, ethyl gallate, hydroxy phenyl acetic acid, three phenylacetic acid isomers, 3-(4-hydroxyphenyl)propionic acid, and homoveratric acid...
January 15, 2017: Food Chemistry
Md Saruar Bhuiyan, Felix Ellett, Gerald L Murray, Xenia Kostoulias, Gustavo M Cerqueira, Keith E Schulze, Mohd Hafidz Mahamad Maifiah, Jian Li, Darren J Creek, Graham J Lieschke, Anton Y Peleg
Innate cellular immune responses are a critical first-line defense against invading bacterial pathogens. Leukocyte migration from the bloodstream to a site of infection is mediated by chemotactic factors that are often host-derived. More recently, there has been a greater appreciation of the importance of bacterial factors driving neutrophil movement during infection. Here, we describe the development of a zebrafish infection model to study Acinetobacter baumannii pathogenesis. By using isogenic A. baumannii mutants lacking expression of virulence effector proteins, we demonstrated that bacterial drivers of disease severity are conserved between zebrafish and mammals...
August 23, 2016: Proceedings of the National Academy of Sciences of the United States of America
Ayeman Amanullah, Arun Upadhyay, Deepak Chhangani, Vibhuti Joshi, Ribhav Mishra, Koji Yamanaka, Amit Mishra
Diclofenac is the most commonly used phenylacetic acid derivative non-steroidal anti-inflammatory drug (NSAID) that demonstrates significant analgesic, antipyretic, and anti-inflammatory effects. Several epidemiological studies have demonstrated anti-proliferative activity of NSAIDs and examined their apoptotic induction effects in different cancer cell lines. However, the precise molecular mechanisms by which these pharmacological agents induce apoptosis and exert anti-carcinogenic properties are not well known...
August 2, 2016: Journal of Cellular Biochemistry
Cláudia S L Vicente, Francisco X Nascimento, Pedro Barbosa, Huei-Mien Ke, Isheng J Tsai, Tomonori Hirao, Peter J A Cock, Taisei Kikuchi, Koichi Hasegawa, Manuel Mota
Pine wilt disease (PWD) results from the interaction of three elements: the pathogenic nematode, Bursaphelenchus xylophilus; the insect-vector, Monochamus sp.; and the host tree, mostly Pinus species. Bacteria isolated from B. xylophilus may be a fourth element in this complex disease. However, the precise role of bacteria in this interaction is unclear as both plant-beneficial and as plant-pathogenic bacteria may be associated with PWD. Using whole genome sequencing and phenotypic characterization, we were able to investigate in more detail the genetic repertoire of Serratia marcescens PWN146, a bacterium associated with B...
October 2016: Microbial Ecology
Shaoyu Mai, Yingwei Zhao, Qiuling Song
C-N bond formation via a copper-catalyzed aerobic oxidative decarboxylative tandem protocol was realized. The phenylacetic acids which contain ortho-X (X = F or Br) on the aromatic ring will render a fused five-membered heterocycle via a tandem aromatic nucleophilic substitution and aerobic oxidative decarboxylative acylation at the C(sp(2))-H bond of benzimidazoles under the Cu(OAc)2/K2CO3/BF3·Et2O catalytic system, while with CuBr as the catalyst and pyridine as the base, N-acylation occurred and tertiary amides were obtained...
October 7, 2016: Organic & Biomolecular Chemistry
Łukasz Popiołek, Anna Biernasiuk
In this study 30 hydrazide-hydrazones of phenylacetic (3-10) and hydroxyacetic acid (11-32) were synthesized by the condensation reaction of appropriate 2-substituted acetic acid hydrazide with different aromatic aldehydes. The obtained compounds were characterized by spectral data and evaluated in vitro for their potential antimicrobial activities against a panel of reference strains of microorganisms, including Gram-positive bacteria, Gram-negative bacteria and fungi belonging to the Candida spp. The results from our antimicrobial assays indicated that among synthesized compounds 3-32, especially compounds 6, 14 and 26 showed high bactericidal activity (MIC = 0...
July 16, 2016: Chemical Biology & Drug Design
Rafael Rodríguez, Emilio Quiñoá, Ricardo Riguera, Félix Freire
The remarkable consequences in elongation, dynamic character, response to external stimuli (e.g., solvent effects, metal cations), and aggregation observed in helical poly(phenylacetylene)s (PPAs) when either the type of linkage with the pendant groups (i.e., anilide, benzamide) or the aromatic substitution pattern (i.e., ortho, meta, para) of the parent phenylacetylene monomer undergo modification are analyzed in depth. Two series of PPAs substituted at the phenyl ring in ortho, meta, and para with either (S)-α-methoxy-α-phenylacetic acid (MPA) or (S)-phenylglycine methyl ester (PGME) linked through anilide or benzamide bonds were prepared (i...
August 3, 2016: Journal of the American Chemical Society
Jinsong Han, Benhua Wang, Markus Bender, Kai Seehafer, Uwe H F Bunz
A chemical tongue consisting of 11 elements (four poly(p-aryleneethynylene)s (PAE) at pH 7 and pH 13, and seven electrostatic complexes formed from oppositely charged poly(p-aryleneethynylene)s at pH 7) discriminate 21 benzoic and phenylacetic acid derivatives in aqueous solution. The mechanism of discrimination is the fluorescence modulation of the PAEs, leading to quenching or fluorescence turn-on. The PAEs alone at both pH values and the tongue, consisting of the complexes only, discriminate the 21 acids with 92% (PAEs at pH 7), 95% (PAEs at pH 13), and 99% (complexes at pH 7) reliability after linear discriminant analysis (LDA)...
August 10, 2016: ACS Applied Materials & Interfaces
Russell J Perkins, Alexandra Kukharchuk, Pauline Delcroix, Richard K Shoemaker, Martina Roeselová, Lukasz Cwiklik, Veronica Vaida
Phenylalanine has an important role both in normal biological function and in disease states such as phenylketonuria (PKU) and amyloid fibril diseases. Two crucial aspects of phenylalanine behavior in biological systems are its preferential partitioning into membranes and its propensity to cluster. In order to examine the intermolecular interactions that give rise to this behavior, the surface partitioning behavior was investigated for a series of molecules structurally related to phenylalanine (phenylglycine, phenylacetic acid, and tyrosine) both experimentally and by molecular dynamics simulations...
August 4, 2016: Journal of Physical Chemistry. B
Lina M Acosta Quintero, Alirio Palma, Justo Cobo, Christopher Glidewell
Compounds containing the tricyclic dibenzo[b,e]azepine system have potential activity in the treatment of a number of diseases. Continuing with our studies on the synthesis of new small and potentially bioactive molecules, a synthetic route, involving acid-catalysed intramolecular Friedel-Crafts cyclization, to the readily separable diastereoisomers of 11-ethyl-6,11-dihydro-5H-dibenzo[b,e]azepine-6-carboxamide, a potentially useful precursor in the synthesis of analogues of some anti-allergenic, antidepressant and antihistaminic drugs currently in use, has been developed starting from 2-allylphenylamine and methyl 2-bromo-2-phenylacetate and proceeding via racemic methyl 2-[(2-allylphenyl)amino]-2-phenylacetate (A) and racemic 2-[(2-allylphenyl)amino]-2-phenylacetamide (B), to give the two diastereoisomers (I) and (II), C17H18N2O...
July 1, 2016: Acta Crystallographica. Section C, Structural Chemistry
Dimitrios Tsikas, Arslan Arinc Kayacelebi, Erik Hanff, Anja Mitschke, Bibiana Beckmann, Hanns-Christian Tillmann, Frank-Mathias Gutzki, Meike Müller, Corrado Bernasconi
GC-MS and GC-MS/MS methods were developed and validated for the quantitative determination of ibuprofen (d0-ibuprofen), a non-steroidal anti-inflammatory drug (NSAID), in human plasma using α-methyl-(2)H3-4-(isobutyl)phenylacetic acid (d3-ibuprofen) as internal standard. Plasma (10μL) was diluted with acetate buffer (80μL, 1M, pH 4.9) and d0- and d3-ibuprofen were extracted with ethyl acetate (2×500μL). After solvent evaporation d0- and d3-ibuprofen were derivatized in anhydrous acetonitrile by using pentafluorobenzyl (PFB) bromide and N,N-diisopropylethylamine as the base catalyst...
June 9, 2016: Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences
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