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Phenylacetic acid

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https://www.readbyqxmd.com/read/28225105/elucidating-the-biosynthetic-pathways-of-volatile-organic-compounds-in-mycobacterium-tuberculosis-through-a-computational-approach
#1
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
#2
Ville Mikael 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 16, 2017: Journal of Agricultural and Food Chemistry
https://www.readbyqxmd.com/read/28178425/synthetic-cystic-fibrosis-sputum-medium-diminishes-i-burkholderia-cenocepacia-i-antifungal-activity-against-i-aspergillus-fumigatus-i-independently-of-phenylacetic-acid-production
#3
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 three microbial pathogens of the cystic fibrosis (CF) lung microbiome: <i>Pseudomonas aeruginosa</i>, <i>Burkholderia cenocepacia</i> and <i>Aspergillus fumigatus</i>. While <i>in silico</i> analysis of <i>B. cenocepacia</i> J2315 and <i>A...
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
#4
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
#5
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...
January 22, 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
#6
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
#7
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
#8
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
https://www.readbyqxmd.com/read/28029051/adherence-to-a-mediterranean-diet-influences-the-fecal-metabolic-profile-of-microbial-derived-phenolics-in-a-spanish-cohort-of-middle-age-and-older-people
#9
Isabel Gutiérrez-Díaz, Tania Fernández-Navarro, Nuria Salazar, Begoña Bartolomé, M Victoria Moreno-Arribas, Enrique Juan de Andres-Galiana, Juan Luis Fernández-Martínez, Clara G de Los Reyes-Gavilán, Miguel Gueimonde, Sonia González
Despite the evidence regarding the influence of certain polyphenol food sources on the metabolic profile in feces, the association between the different phenolics provided by the diet and the fecal phenolic profile has not been elucidated. In this study, the composition of phenolic metabolites in fecal solutions was analyzed by UPLC-ESI-MS/MS in 74 volunteers. This fecal phenolic profile showed a high interindividual variation of the different compounds analyzed, phenylacetic and phenylpropionic acids being the major classes of phenolic metabolites excreted in feces...
January 11, 2017: Journal of Agricultural and Food Chemistry
https://www.readbyqxmd.com/read/28025550/targeted-metabolomic-analysis-of-polyphenols-with-antioxidant-activity-in-sour-guava-psidium-friedrichsthalianum-nied-fruit
#10
Carmen Tatiana Cuadrado-Silva, Maria Ángeles Pozo-Bayón, Coralia Osorio
Psidium is a genus of tropical bushes belonging to the Myrtaceae family distributed in Central and South America. The polar extract of Psidium friedrichsthalianum Nied. was partitioned with ethyl ether, ethyl acetate, and n-butanol, and the total phenolic content and antioxidant activity were measured by Folin-Ciocalteu and ABTS assays, respectively. The ethyl acetate fraction exhibited both the highest phenolic content and antioxidant activity. Due to the complexity of this fraction, an analytical method for the comprehensive profiling of phenolic compounds was done by UPLC-ESI/QqQ in MRM (multiple reaction monitoring) mode...
December 23, 2016: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28003437/prospective-analyses-of-volatile-organic-compounds-in-obstructive-sleep-apnea-patients
#11
Takuya Aoki, Takashi Nagaoka, Naofumi Kobayashi, Muneshige Kurahashi, Chizuko Tsuji, Hiroto Takiguchi, Katsuyoshi Tomomatsu, Tsuyoshi Oguma, Naoki Kobayashi, Kazushige Magatani, Sunao Takeda, Koichiro Asano, Tadashi Abe
Various volatile organic compounds (VOCs) are known to be toxic. Although exhaled VOC patterns change in obstructive sleep apnea (OSA) patients, individual VOC profiles are not fully determined. The primary outcome was VOC characterizations; secondary outcomes included their relationships with sleep and clinical parameters in OSA patients. We prospectively examined 32 OSA patients with an apnea-hypopnea index (AHI) ≥ 15 by full polysomnography, and 33 age- and sex-matched controls without obvious OSA symptoms...
December 20, 2016: Toxicological Sciences: An Official Journal of the Society of Toxicology
https://www.readbyqxmd.com/read/27889673/conformational-equilibrium-of-phenylacetic-acid-and-its-halogenated-analogues-through-theoretical-studies-nmr-and-ir-spectroscopy
#12
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...
March 5, 2017: Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
https://www.readbyqxmd.com/read/27849615/arabidopsis-thaliana-gh3-5-acyl-acid-amido-synthetase-mediates-metabolic-crosstalk-in-auxin-and-salicylic-acid-homeostasis
#13
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
https://www.readbyqxmd.com/read/27830119/the-first-mongolian-cases-of-phenylketonuria-in-selective-screening-of-inborn-errors-of-metabolism
#14
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
https://www.readbyqxmd.com/read/27808586/the-auxins-iaa-and-paa-are-synthesized-by-similar-steps-catalyzed-by-different-enzymes
#15
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 2016: Plant Signaling & Behavior
https://www.readbyqxmd.com/read/27779841/reinvestigation-of-the-absolute-configurations-of-chiral-%C3%AE-mercaptoalkanones-using-vibrational-circular-dichroism-and-1-h-nmr-analysis
#16
Christiane Kiske, Svenja Nörenberg, Miriam Ecker, Xingyue Ma, Tohru Taniguchi, Kenji Monde, Wolfgang Eisenreich, Karl-Heinz Engel
The absolute configurations of chiral β-mercaptoalkanones were previously assigned on the basis of the (1)H NMR anisotropy method using (S)-2-methoxy-2-(1-naphthyl)propionic acid ((S)-MαNP) as the 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 based on 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...
November 16, 2016: Journal of Agricultural and Food Chemistry
https://www.readbyqxmd.com/read/27670220/rifm-fragrance-ingredient-safety-assessment-linalyl-benzoate-cas-registry-number-126-64-7
#17
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...
November 2016: Food and Chemical Toxicology
https://www.readbyqxmd.com/read/27592363/in-silico-screening-and-evaluation-of-the-anticonvulsant-activity-of-docosahexaenoic-acid-like-molecules-in-experimental-models-of-seizures
#18
Ali Gharibi Loron, Soroush Sardari, Jamshid Narenjkar, Mohammad Sayyah
BACKGROUND: Resistance to antiepileptic drugs and the 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, the biological activity score of Professional Association for SQL Server, and structural requirements suggested by pharmacophore design...
January 2017: Iranian Biomedical Journal
https://www.readbyqxmd.com/read/27578531/characterization-and-genome-functional-analysis-of-a-novel-metamitron-degrading-strain-rhodococcus-sp-met-via-both-triazinone-and-phenyl-rings-cleavage
#19
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...
August 31, 2016: Scientific Reports
https://www.readbyqxmd.com/read/27552288/site-directed-chemical-mutations-on-abzymes-large-rate-accelerations-in-the-catalysis-by-exchanging-the-functionalized-small-nonprotein-components
#20
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
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