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Phenylacetic acid

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https://www.readbyqxmd.com/read/28513572/synthesis-and-antiradical-activity-of-isoquercitrin-esters-with-aromatic-acids-and-their-homologues
#1
Eva Heřmánková-Vavříková, Alena Křenková, Lucie Petrásková, Christopher Steven Chambers, Jakub Zápal, Marek Kuzma, Kateřina Valentová, Vladimír Křen
Isoquercitrin, (IQ, quercetin-3-O-β-d-glucopyranoside) is known for strong chemoprotectant activities. Acylation of flavonoid glucosides with carboxylic acids containing an aromatic ring brings entirely new properties to these compounds. Here, we describe the chemical and enzymatic synthesis of a series of IQ derivatives at the C-6″. IQ benzoate, phenylacetate, phenylpropanoate and cinnamate were prepared from respective vinyl esters using Novozym 435 (Lipase B from Candida antarctica immobilized on acrylic resin)...
May 17, 2017: International Journal of Molecular Sciences
https://www.readbyqxmd.com/read/28505407/unique-n-phenylacetylation-and-nrps-with-substrate-promiscuity-for-biosynthesis-of-heptapeptide-variants-jbir-78-and-jbir-95
#2
Kunpei Takeda, Kohei Kemmoku, Yasuharu Satoh, Yasushi Ogasawara, Kazuo Shin-Ya, Tohru Dairi
JBIR-78 (1) and JBIR-95 (2), both of which are heptapeptide derivatives isolated from Kibdelosporangium sp. AK-AA56, have the same amino acid sequences except for the second amino acid; phenylacetic acid (Paa)-L-Val-D-Asp (1)/D-cysteic acid (2)-L-Ala-(3S)-3-hydroxy-D-Leu-Gly-D-Ala-L-Phe. Heterologous expression of the biosynthetic gene cluster including genes encoding non-ribosomal peptide synthetases (NRPS) and in vitro assays with recombinant Orf3, L-cysteic acid synthase homolog, suggested the single A-domain in module 2 activates both L-Asp and L-cysteic acid to yield 1 and 2, respectively, although the substrate specificities of the A-domains of NRPSs are usually strict...
May 15, 2017: ACS Chemical Biology
https://www.readbyqxmd.com/read/28485900/ligand-enabled-auxiliary-free-meta-c-h-arylation-of-phenylacetic-acids
#3
Gen-Cheng Li, Peng Wang, Marcus E Farmer, Jin-Quan Yu
The meta-C-H arylation of free phenylacetic acid was realized using 2-carbomethoxynorbornene (NBE-CO2 Me) as a transient mediator. Both the modified norbornene and the mono-protected 3-amino-2-hydroxypyridine type ligand are crucial for this auxiliary-free meta-C-H arylation reaction. A series of phenylacetic acids, including mandelic acid and phenylglycine, react smoothly with various aryl iodides to provide the meta-arylated products in high yields.
May 9, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28450070/synthesis-of-androstene-oxime-nitrogen-mustard-bioconjugates-as-potent-antineoplastic-agents
#4
Pratap Chandra Acharya, Ranju Bansal
In the present study, synthesis and antineoplastic activity of phenylacetic acid and benzoic acid nitrogen mustard conjugates of various steroidal oximes are reported for the first time. The conjugation was achieved through a more stable oxime-ester linkage and the resulting newly synthesized conjugates were evaluated in vitro on various human cancer cell lines for cytotoxicity. The extent of their alkylating activity was investigated by the in vitro colorimetric 4-(p-nitrobenzyl)pyridine (NBP) assay. The 17E-steroidal oxime-benzoic acid mustard ester 3β-acetoxy-17E-[p-(N,N-bis(2-chloroethyl)amino)]benzoyloxyimino-androst-5-ene (8) emerged as the most potent conjugate having significant cytotoxicity on most of the NCI 60-cell lines...
April 24, 2017: Steroids
https://www.readbyqxmd.com/read/28433873/ph-dependent-synthesis-of-two-isomeric-dinuclear-cerium-ii-complexes-structures-dna-interactions-cytotoxic-activity-and-apoptotic-study
#5
En-Jun Gao, Jun-Qi Su, Hai-Tao Jin, Si-Jia Liu, Fu-Chen Zhao, Yang Meng, Xiao-Yu Ma, Jing Ge, Ya-Guang Sun, Wanzhong Zhang, Ming-Chang Zhu
Two isomeric dinuclear Cerium(II) complexes 1 and 2, formulated as Ce2(phen)2(NO3)2(L)4 [L=phenylacetic acid, phen=1,10-phenanthroline] was synthesized under solvothermal conditions at different pH values. The two complexes were characterized by elemental analysis, IR and single crystal X-ray diffraction. Complexes 1 and 2 were studied the binding with DNA and against cytotoxic activity. Fluorescence analysis indicated that the two complexes can bind to DNA. The changes with different gradient concentration of DNA added into the complexes in absorption spectra show a strongπ-stacking interaction between the complexes and DNA base pairs...
April 11, 2017: Journal of Photochemistry and Photobiology. B, Biology
https://www.readbyqxmd.com/read/28372215/key-volatile-aroma-compounds-of-lactic-acid-fermented-malt-based-beverages-impact-of-lactic-acid-bacteria-strains
#6
Sorelle Nsogning Dongmo, Bertram Sacher, Hubert Kollmannsberger, Thomas Becker
This study aims to define the aroma composition and key aroma compounds of barley malt wort beverages produced from fermentation using six lactic acid bacteria (LAB) strains. Gas chromatography mass spectrometry-olfactometry and flame ionization detection was employed; key aroma compounds were determined by means of aroma extract dilution analysis. Fifty-six detected volatile compounds were similar among beverages. However, significant differences were observed in the concentration of individual compounds. Key aroma compounds (flavor dilution (FD) factors ≥16) were β-damascenone, furaneol, phenylacetic acid, 2-phenylethanol, 4-vinylguaiacol, sotolon, methional, vanillin, acetic acid, nor-furaneol, guaiacol and ethyl 2-methylbutanoate...
August 15, 2017: Food Chemistry
https://www.readbyqxmd.com/read/28345352/metal-free-photoinduced-electron-transfer-atom-transfer-radical-polymerization-integrated-with-bioinspired-polydopamine-chemistry-as-a-green-strategy-for-surface-engineering-of-magnetic-nanoparticles
#7
Yang Yang, Xuegang Liu, Gang Ye, Shan Zhu, Zhe Wang, Xiaomei Huo, Krzysztof Matyjaszewski, Yuexiang Lu, Jing Chen
Developing green and efficient technologies for surface modification of magnetic nanoparticles (MNPs) is of crucial importance for their biomedical and environmental applications. This study reports, for the first time, a novel strategy by integrating metal-free photoinduced electron transfer-atom transfer radical polymerization (PET-ATRP) with the bioinspired polydopamine (PDA) chemistry for controlled architecture of functional polymer brushes from MNPs. Conformal PDA encapsulation layers were initially generated on the surfaces of MNPs, which served as the protective shells while providing an ideal platform for tethering 2-bromo-2-phenylacetic acid (BPA), a highly efficient initiator...
April 5, 2017: ACS Applied Materials & Interfaces
https://www.readbyqxmd.com/read/28289081/light-modulates-metabolic-pathways-and-other-novel-physiological-traits-in-the-human-pathogen-acinetobacter-baumannii
#8
Gabriela L Müller, Marisel Tuttobene, Matías Altilio, Maitena Martínez Amezaga, Meaghan Nguyen, Pamela Cribb, Larisa E Cybulski, María Soledad Ramírez, Silvia Altabe, María Alejandra Mussi
Light sensing in chemotrophic bacteria has been relatively recently ascertained. In the human pathogen Acinetobacter baumannii, light modulates motility, biofilm formation, and virulence through the blue-light-sensing-using flavin (BLUF) photoreceptor BlsA. In addition, light can induce a reduction in susceptibility to certain antibiotics, such as minocycline and tigecycline, in a photoreceptor-independent manner. In this work, we identified new traits whose expression levels are modulated by light in this pathogen, which comprise not only important determinants related to pathogenicity and antibiotic resistance but also metabolic pathways, which represents a novel concept for chemotrophic bacteria...
May 15, 2017: Journal of Bacteriology
https://www.readbyqxmd.com/read/28287476/absorption-metabolism-and-excretion-of-cranberry-poly-phenols-in-humans-a-dose-response-study-and-assessment-of-inter-individual-variability
#9
Rodrigo P Feliciano, Charlotte E Mills, Geoffrey Istas, Christian Heiss, Ana Rodriguez-Mateos
The beneficial health effects of cranberries have been attributed to their (poly)phenol content. Recent studies have investigated the absorption, metabolism and excretion of cranberry (poly)phenols; however, little is known about whether they follow a dose response in vivo at different levels of intake. An acute double-blind randomized controlled trial in 10 healthy men with cranberry juices containing 409, 787, 1238, 1534 and 1910 mg total (poly)phenols was performed. Blood and urine were analyzed by UPLC-Q-TOF-MS...
March 11, 2017: Nutrients
https://www.readbyqxmd.com/read/28283530/identification-of-enzymes-involved-in-oxidation-of-phenylbutyrate
#10
Neža Palir, Jos P N Ruiter, Ronald J A Wanders, Riekelt H Houtkooper
In recent years the short-chain fatty acid, 4-phenylbutyrate (PB), has emerged as a promising drug for various clinical conditions. In fact, PB has been Food and Drug Administration-approved for urea cycle disorders since 1996. PB is more potent and less toxic than its metabolite, phenylacetate (PA), and is not just a pro-drug for PA, as was initially assumed. The metabolic pathway of PB, however, has remained unclear. Therefore, we set out to identify the enzymes involved in the β-oxidation of PB. We used cells deficient in specific steps of fatty acid β-oxidation and ultra-HPLC to measure which enzymes were able to convert PB or its downstream products...
May 2017: Journal of Lipid Research
https://www.readbyqxmd.com/read/28276654/a-family-13-thioesterase-isolated-from-an-activated-sludge-metagenome-insights-into-aromatic-compounds-metabolism
#11
Ayixon Sánchez-Reyez, Ramón Alberto Batista-García, Gilberto Valdés-García, Ernesto Ortiz, Lucía Perezgasga, Andrés Zárate-Romero, Nina Pastor, Jorge Luis Folch-Mallol
Activated sludge is produced during the treatment of sewage and industrial wastewaters. Its diverse chemical composition allows growth of a large collection of microbial phylotypes with very different physiologic and metabolic profiles. Thus, activated sludge is considered as an excellent environment to discover novel enzymes through functional metagenomics, especially activities related with degradation of environmental pollutants. Metagenomic DNA was isolated and purified from an activated sludge sample. Metagenomic libraries were subsequently constructed in Escherichia coli...
March 9, 2017: Proteins
https://www.readbyqxmd.com/read/28239416/biodegradation-of-alkaline-lignin-by-bacillus-ligniniphilus-l1
#12
Daochen Zhu, Peipei Zhang, Changxiao Xie, Weimin Zhang, Jianzhong Sun, Wei-Jun Qian, Bin Yang
BACKGROUND: Lignin is the most abundant aromatic biopolymer in the biosphere and it comprises up to 30% of plant biomass. Although lignin is the most recalcitrant component of the plant cell wall, still there are microorganisms able to decompose it or degrade it. Fungi are recognized as the most widely used microbes for lignin degradation. However, bacteria have also been known to be able to utilize lignin as a carbon or energy source. Bacillus ligniniphilus L1 was selected in this study due to its capability to utilize alkaline lignin as a single carbon or energy source and its excellent ability to survive in extreme environments...
2017: Biotechnology for Biofuels
https://www.readbyqxmd.com/read/28225105/elucidating-the-biosynthetic-pathways-of-volatile-organic-compounds-in-mycobacterium-tuberculosis-through-a-computational-approach
#13
Purva Bhatter, Karthik Raman, Vani Janakiraman
Microbial volatile organic compounds (VOCs) have gained prominence in the recent past for their potential use as disease markers. The discovery of microbial VOCs has benefited 'difficult to detect' diseases such as tuberculosis (TB). Few of the identified VOCs of Mycobacterium tuberculosis (Mtb) are currently being explored for their diagnostic potential. However, very little is known about the biosynthesis of these small lipophilic molecules. Here, we propose putative biosynthetic pathways in Mycobacterium tuberculosis for three VOCs, namely methyl nicotinate, methyl phenylacetate and methyl p-anisate, using computational approaches...
February 22, 2017: Molecular BioSystems
https://www.readbyqxmd.com/read/28206756/effect-of-bioprocessing-on-the-in-vitro-colonic-microbial-metabolism-of-phenolic-acids-from-rye-bran-fortified-breads
#14
Ville M Koistinen, Emilia Nordlund, Kati Katina, Ismo Mattila, Kaisa Poutanen, Kati Hanhineva, Anna-Marja Aura
Cereal bran is an important source of dietary fiber and bioactive compounds, such as phenolic acids. We aimed to study the phenolic acid metabolism of native and bioprocessed rye bran fortified refined wheat bread and to elucidate the microbial metabolic route of phenolic acids. After incubation in an in vitro colon model, the metabolites were analyzed using two different methods applying mass spectrometry. While phenolic acids were released more extensively from the bioprocessed bran bread and ferulic acid had consistently higher concentrations in the bread type during fermentation, there were only minor differences in the appearance of microbial metabolites, including the diminished levels of certain phenylacetic acids in the bioprocessed bran...
February 28, 2017: Journal of Agricultural and Food Chemistry
https://www.readbyqxmd.com/read/28178425/synthetic-cystic-fibrosis-sputum-medium-diminishes-burkholderia-cenocepacia-antifungal-activity-against-aspergillus-fumigatus-independently-of-phenylacetic-acid-production
#15
Tasia Joy Lightly, Ryan R Phung, John L Sorensen, Silvia T Cardona
Phenylacetic acid (PAA), an intermediate of phenylalanine degradation, is emerging as a signal molecule in microbial interactions with the host. In this work, we explore the presence of phenylalanine and PAA catabolism in 3 microbial pathogens of the cystic fibrosis (CF) lung microbiome: Pseudomonas aeruginosa, Burkholderia cenocepacia, and Aspergillus fumigatus. While in silico analysis of B. cenocepacia J2315 and A. fumigatus Af293 genome sequences showed complete pathways from phenylalanine to PAA, the P...
February 8, 2017: Canadian Journal of Microbiology
https://www.readbyqxmd.com/read/28153386/structure-and-biochemistry-of-phenylacetaldehyde-dehydrogenase-from-the-pseudomonas-putida-s12-styrene-catabolic-pathway
#16
Anders G Crabo, Baljit Singh, Tim Nguyen, Shahram Emami, George T Gassner, Matthew H Sazinsky
Phenylacetaldehyde dehydrogenase catalyzes the NAD(+)-dependent oxidation of phenylactealdehyde to phenylacetic acid in the styrene catabolic and detoxification pathway of Pseudomonas putida (S12). Here we report the structure and mechanistic properties of the N-terminally histidine-tagged enzyme, NPADH. The 2.83 Å X-ray crystal structure is similar in fold to sheep liver cytosolic aldehyde dehydrogenase (ALDH1), but has unique set of intersubunit interactions and active site tunnel for substrate entrance...
February 15, 2017: Archives of Biochemistry and Biophysics
https://www.readbyqxmd.com/read/28152429/synthesis-and-biological-evaluation-of-fluorinated-n-benzoyl-and-n-phenylacetoyl-derivatives-of-3-4-aminophenyl-coumarin-7-o-sulfamate-as-steroid-sulfatase-inhibitors
#17
Mateusz Daśko, Maja Przybyłowska, Janusz Rachon, Maciej Masłyk, Konrad Kubiński, Majus Misiak, Andrzej Składanowski, Sebastian Demkowicz
In the present work, we report convenient methods for the synthesis of 3-(4-aminophenyl)-coumarin-7-O-sulfamate derivatives N-acylated with fluorinated analogues of benzoic or phenylacetic acid as steroid sulfatase (STS) inhibitors. The design of these potential STS inhibitors was supported by molecular modeling techniques. Additionally, computational docking methods were used to determine the binding modes of the synthesized inhibitors and to identify potential interactions between inhibitors and amino acid residues located in the active site of STS...
March 10, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28098847/polish-yellow-sweet-clover-melilotus-officinalis-l-honey-chromatographic-fingerprints-and-chemical-markers
#18
Izabela Jasicka-Misiak, Ewa Makowicz, Natalia Stanek
A case study of Polish Melilotus officinalis honey was presented for the first time. Gas chromatography-mass spectrometry (GC-MS) (after steam distillation, Soxhlet extraction, ultrasonic solvent extraction, and solid phase extraction (SPE)) and targeted high performance liquid chromatography with a photodiode array detector (HPLC-PAD) were applied to determine the characteristic components of honey. While ubiquitous in most honeys, carbohydrates, terpene derivatives, and phenylacetic acid dominated in the Soxhlet extracts (25...
January 15, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28071050/hydroxytyrosol-and-the-colonic-metabolites-derived-from-virgin-olive-oil-intake-induce-cell-cycle-arrest-and-apoptosis-in-colon-cancer-cells
#19
Maria-Carmen López de Las Hazas, Carme Piñol, Alba Macià, Maria-José Motilva
After the sustained consumption of virgin olive oil (VOO), the unabsorbed native phenols (mainly hydroxytyrosol (HT)) are transformed into its catabolites in the intestine by microbials. The role of these catabolites in preventing colon cancer has not been sufficiently investigated. This work aims to study the antiproliferative and apoptotic activities in colon (Caco-2; HT-29) cancer cell lines of the main catabolites detected in human feces (phenylacetic, phenylpropionic, hydroxyphenylpropionic, and dihydroxyphenylpropionic acids and catechol), after the sustained VOO intake...
January 19, 2017: Journal of Agricultural and Food Chemistry
https://www.readbyqxmd.com/read/28062952/characterization-of-aldehyde-dehydrogenases-applying-an-enzyme-assay-with-in-situ-formation-of-phenylacetaldehydes
#20
Juliane Zimmerling, Dirk Tischler, Carolin Großmann, Michael Schlömann, Michel Oelschlägel
Herein, different dehydrogenases (DH) were characterized by applying a novel two-step enzyme assay. We focused on the NAD(P)(+)-dependent phenylacetaldehyde dehydrogenases because they produce industrially relevant phenylacetic acids, but they are not well studied due to limited substrate availability. The first assay step comprises a styrene oxide isomerase (440 U mg(-1)protein) which allows the production of pure phenylacetaldehydes (>70 mmol L(-1)) from commercially available styrene oxides. Thereafter, a DH of interest can be added to convert phenylacetaldehydes in a broad concentration range (0...
January 6, 2017: Applied Biochemistry and Biotechnology
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