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indole hydroxylation

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https://www.readbyqxmd.com/read/28821467/in-vitro-characterization-of-cyp102g4-from-streptomyces-cattleya-a-self-sufficient-p450-naturally-producing-indigo
#1
Joonwon Kim, Pyung-Gang Lee, Eun-Ok Jung, Byung-Gee Kim
Self-sufficient CYP102As possess outstanding hydroxylating activity to fatty acids such as myristic acid. Other CYP102 subfamily members share substrate specificity of CYP102As, but, occasionally, unusual characteristics of its own subfamily have been found. In this study, only one self-sufficient cytochrome P450 from Streptomyces cattleya was renamed from CYP102A_scat to CYP102G4, purified and characterized. UV-Vis spectrometry pattern, FAD/FMN analysis, and protein sequence comparison among CYP102s have shown that CYP102 from Streptomyces cattleya belongs to CYP102G subfamily...
August 15, 2017: Biochimica et Biophysica Acta
https://www.readbyqxmd.com/read/28795267/cyp79-p450-monooxygenases-in-gymnosperms-cyp79a118-is-associated-with-the-formation-of-taxiphyllin-in-taxus-baccata
#2
Katrin Luck, Qidong Jia, Meret Huber, Vinzenz Handrick, Gane Ka-Shu Wong, David R Nelson, Feng Chen, Jonathan Gershenzon, Tobias G Köllner
Conifers contain P450 enzymes from the CYP79 family that are involved in cyanogenic glycoside biosynthesis. Cyanogenic glycosides are secondary plant compounds that are widespread in the plant kingdom. Their biosynthesis starts with the conversion of aromatic or aliphatic amino acids into their respective aldoximes, catalysed by N-hydroxylating cytochrome P450 monooxygenases (CYP) of the CYP79 family. While CYP79s are well known in angiosperms, their occurrence in gymnosperms and other plant divisions containing cyanogenic glycoside-producing plants has not been reported so far...
August 9, 2017: Plant Molecular Biology
https://www.readbyqxmd.com/read/28743672/membrane-bound-human-orphan-cytochrome-p450-2u1-sequence-singularities-construction-of-a-full-3d-model-and-substrate-docking
#3
Lionel Ducassou, Laura Dhers, Gabriella Jonasson, Nicolas Pietrancosta, Jean-Luc Boucher, Daniel Mansuy, François André
BACKGROUND: Human cytochrome P450 2U1 (CYP2U1) is an orphan CYP that exhibits several distinctive characteristics among the 57 human CYPs with a highly conserved sequence in almost all living organisms. METHODS: We compared its protein sequence with those of the 57 human CYPs and constructed a 3D structure of a full-length CYP2U1 model bound to a POPC membrane. We also performed docking experiments of arachidonic acid (AA) and N-arachidonoylserotonin (AS) in this model...
September 2017: Biochimie
https://www.readbyqxmd.com/read/28686036/synthesis-of-thieno-fused-five-and-six-membered-nitrogen-and-oxygen-heterocycles-via-intramolecular-heteroannulation-of-4-5-substituted-3-amino-or-3-hydroxy-2-functionalized-thiophenes
#4
Anand Acharya, Vibha Gautam, Hiriyakkanavar Ila
Diverse general high-yield routes for novel thieno-fused five- and six-membered nitrogen and oxygen heterocycles such as thieno[3,2-b]pyrroles, thieno[3,2-b]furans, thieno[3,2-b]indoles, thieno[3,2-b]benzofurans, thieno[3,2-b]pyridine-5-ones, thieno[3,2-b]pyran-5-ones, thieno[3,2-b]isoquinolin-5-ones, thieno[3,2-b]chromen-5-ones, thieno[3,2-b]quinolin-9-ones, and thieno[3,2-b]chromen-9-ones have been developed via in situ or stepwise intramolecular heteroannulation of newly synthesized 4,5-substituted 3-amino- or 3-hydroxy 2-functionalized thiophenes...
July 18, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28643772/cryptic-indole-hydroxylation-by-a-non-canonical-terpenoid-cyclase-parallels-bacterial-xenobiotic-detoxification
#5
Susann Kugel, Martin Baunach, Philipp Baer, Mie Ishida-Ito, Srividhya Sundaram, Zhongli Xu, Michael Groll, Christian Hertweck
Terpenoid natural products comprise a wide range of molecular architectures that typically result from C-C bond formations catalysed by classical type I/II terpene cyclases. However, the molecular diversity of biologically active terpenoids is substantially increased by fully unrelated, non-canonical terpenoid cyclases. Their evolutionary origin has remained enigmatic. Here we report the in vitro reconstitution of an unusual flavin-dependent bacterial indoloterpenoid cyclase, XiaF, together with a designated flavoenzyme-reductase (XiaP) that mediates a key step in xiamycin biosynthesis...
June 15, 2017: Nature Communications
https://www.readbyqxmd.com/read/28505547/synthesis-of-indole-analogs-as-potent-%C3%AE-glucuronidase-inhibitors
#6
Mohd Syukri Baharudin, Muhammad Taha, Syahrul Imran, Nor Hadiani Ismail, Fazal Rahim, Muhammad Tariq Javid, Khalid Mohammed Khan, Muhammad Ali
Natural products are the main source of motivation to design and synthesize new molecules for drug development. Designing new molecules against β-glucuronidase inhibitory is utmost essential. In this study indole analogs (1-35) were synthesized, characterized using various spectroscopic techniques including (1)H NMR and EI-MS and evaluated for their β-glucuronidase inhibitory activity. Most compounds were identified as potent inhibitors for the enzyme with IC50 values ranging between 0.50 and 53.40μM, with reference to standard d-saccharic acid 1,4-lactone (IC50=48...
June 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/28476332/in-vivo-%C3%AE-hydroxylation-of-a-2-alkylindole-antagonist-of-the-oxe-receptor-for-the-eosinophil-chemoattractant-5-oxo-6-8-11-14-eicosatetraenoic-acid-in-monkeys
#7
Shishir Chourey, Qiuji Ye, Chintam Nagendra Reddy, Chantal Cossette, Sylvie Gravel, Matthias Zeller, Irina Slobodchikova, Dajana Vuckovic, Joshua Rokach, William S Powell
We have developed a selective indole antagonist (230) targeting the OXE receptor for the potent eosinophil chemoattractant 5-oxo-ETE (5-oxo-6,8,11,14-eicosatetraenoic acid), that may be useful for the treatment of eosinophilic diseases such as asthma. In previous studies we identified ω2-oxidation of the hexyl side chain of racemic 230 as a major metabolic route in monkeys, but also obtained evidence for another pathway that appeared to involve hydroxylation of the hexyl side chain close to the indole. The present study was designed to investigate the metabolism of the active S-enantiomer of 230 (S230) and to identify the novel hydroxy metabolite and its chirality...
August 15, 2017: Biochemical Pharmacology
https://www.readbyqxmd.com/read/28466505/total-synthesis-of-%C3%A2-corymine
#8
Benxiang Zhang, Xiaoqing Wang, Chao Cheng, Deqian Sun, Chaozhong Li
The first total synthesis of the hexacyclic indole alkaloid (±)-corymine is described. Starting from the readily available N-protected tryptamine, the title compound was achieved in 21 steps in 3.4 % overall yield. Key steps of the synthesis include: a) the addition of a malonate to a 3-bromooxindole to afford 3,3-disubstituted oxindole, b) the formation of a 12-membered cyclic enol ether by intramolecular O-propargylation, immediately followed by propargyl Claisen rearrangement to provide the α-allenyl ketone stereospecifically, c) DMDO oxidation to install a hydroxy group in a highly stereoselective manner, and d) the SmI2 -mediated reductive C-O bond cleavage to remove the α-keto carboxyl group...
May 3, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28455676/metabolic-profile-of-synthetic-cannabinoids-5f-pb-22-pb-22-xlr-11-and-ur-144-by-cunninghamella-elegans
#9
Shimpei Watanabe, Unnikrishnan Kuzhiumparambil, My Ann Nguyen, Jane Cameron, Shanlin Fu
The knowledge of metabolic profile of synthetic cannabinoids is important for the detection of drugs in urinalysis due to the typical absence or low abundance of parent cannabinoids in human urine. The fungus Cunninghamella elegans has been reported to be a useful tool for metabolism study and thus applicability to synthetic cannabinoid metabolism was examined. In this study, 8-quinolinyl 1-(5-fluoropentyl)-1H-indole-3-carboxylate (5F-PB-22), 8-quinolinyl 1-pentyl-1H-indole-3-carboxylate (PB-22), [1-(5-fluoropentyl)-1H-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)methanone (XLR-11) and (1-pentyl-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone (UR-144) were incubated with C...
April 28, 2017: AAPS Journal
https://www.readbyqxmd.com/read/28443122/membrane-proteomics-of-arabidopsis-glucosinolate-mutants-cyp79b2-b3-and-myb28-29
#10
Islam Mostafa, Mi-Jeong Yoo, Ning Zhu, Sisi Geng, Craig Dufresne, Maged Abou-Hashem, Maher El-Domiaty, Sixue Chen
Glucosinolates (Gls) constitute a major group of natural metabolites represented by three major classes (aliphatic, indolic and aromatic) of more than 120 chemical structures. In our previous work, soluble proteins and metabolites in Arabidopsis mutants deficient of aliphatic (myb28/29) and indolic Gls (cyp79B2B3) were analyzed. Here we focus on investigating the changes at the level of membrane proteins in these mutants. Our LC/MS-MS analyses of tandem mass tag (TMT) labeled peptides derived from the cyp79B2/B3 and myb28/29 relative to wild type resulted in the identification of 4,673 proteins, from which 2,171 are membrane proteins...
2017: Frontiers in Plant Science
https://www.readbyqxmd.com/read/28437060/high-throughput-and-quantitative-measurement-of-microbial-metabolome-by-gas-chromatography-mass-spectrometry-using-automated-alkyl-chloroformate-derivatization
#11
Linjing Zhao, Yan Ni, Mingming Su, Hongsen Li, Fangcong Dong, Wenlian Chen, Runmin Wei, Lulu Zhang, Seu Ping Guiraud, Francois-Pierre Martin, Cynthia Rajani, Guoxiang Xie, Wei Jia
The ability to identify and quantify small molecule metabolites derived from gut microbial-mammalian cometabolism is essential for the understanding of the distinct metabolic functions of the microbiome. To date, analytical protocols that quantitatively measure a complete panel of microbial metabolites in biological samples have not been established but are urgently needed by the microbiome research community. Here, we report an automated high-throughput quantitative method using a gas chromatography/time-of-flight mass spectrometry (GC/TOFMS) platform to simultaneously measure over one hundred microbial metabolites in human serum, urine, feces, and Escherichia coli cell samples within 15 min per sample...
May 2, 2017: Analytical Chemistry
https://www.readbyqxmd.com/read/28435524/pyrano-2-3-4-cd-indole-as-a-scaffold-for-selective-nonbasic-5-ht6r-ligands
#12
Jakub Staroń, Stefan Mordalski, Dawid Warszycki, Grzegorz Satała, Adam Hogendorf, Andrzej J Bojarski
In this letter, we report the synthesis of a pyrano[2,3,4-cd]indole chemical scaffold designed through a tandem bioisostere generation/virtual screening protocol in search of 5-HT6R ligands. The discovered chemical scaffold resulted in the design of highly active basic and nonbasic 5-HT6R ligands (5-HT6R Ki = 1 nM for basic compound 6b and 5-HT6R Ki = 4 nM for its neutral analog 7b). Additionally, molecular modeling suggested that the hydroxyl group of nonbasic ligands 7a-7d forms hydrogen bonds with aspartic acid D(3×32) or D(7...
April 13, 2017: ACS Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28371476/detection-of-the-recently-emerged-synthetic-cannabinoid-5f-mdmb-pica-in-legal-high-products-and-human-urine-samples
#13
Lukas Mogler, Florian Franz, Daniel Rentsch, Verena Angerer, Georg Weinfurtner, Mitchell Longworth, Samuel D Banister, Michael Kassiou, Bjoern Moosmann, Volker Auwärter
Indole or indazole-based synthetic cannabinoids (SCs) bearing substituents derived from valine or tert-leucine are frequently abused new psychoactive substances (NPS). The emergence of 5F-MDMB-PICA (methyl N-{[1-(5-fluoropentyl)-1H-indol-3-yl]carbonyl}-3-methylvalinate) on the German drug market is a further example of a substance synthesized in the context of scientific research being misused by clandestine laboratories by adding it to 'legal high' products. In this work, we present the detection of 5F-MDMB-PICA in several legal high products by gas chromatography-mass spectrometry (GC-MS) analysis...
March 31, 2017: Drug Testing and Analysis
https://www.readbyqxmd.com/read/28343387/hydroxyl-and-methoxyl-derivatives-of-benzylglucosinolate-in-lepidium-densiflorum-with-hydrolysis-to-isothiocyanates-and-non-isothiocyanate-products-substitution-governs-product-type-and-mass-spectral-fragmentation
#14
Eleonora Pagnotta, Niels Agerbirk, Carl E Olsen, Luisa Ugolini, Susanna Cinti, Luca Lazzeri
A system of benzylic glucosinolates was found and characterized in common pepperweed, Lepidium densiflorum Schrad. The major glucosinolate was the novel 4-hydroxy-3,5-dimethoxybenzylglucosinolate (3,5-dimethoxysinalbin), present at high levels in seeds, leaves, and roots. Medium-level glucosinolates were 3,4-dimethoxybenzylglucosinolate and 3,4,5-trimethoxybenzylglucosinolate. Minor glucosinolates included benzylglucosinolate, 3-hydroxy- and 3-methoxybenzylglucosinolate, 4-hydroxybenzylglucosinolate (sinalbin), the novel 4-hydroxy-3-methoxybenzylglucosinolate (3-methoxysinalbin), and indole-type glucosinolates...
April 19, 2017: Journal of Agricultural and Food Chemistry
https://www.readbyqxmd.com/read/28140566/roles-of-copper-and-a-conserved-aspartic-acid-in-the-autocatalytic-hydroxylation-of-a-specific-tryptophan-residue-during-cysteine-tryptophylquinone-biogenesis
#15
Heather R Williamson, Esha Sehanobish, Alan M Shiller, Antonio Sanchez-Amat, Victor L Davidson
The first posttranslational modification step in the biosynthesis of the tryptophan-derived quinone cofactors is the autocatalytic hydroxylation of a specific Trp residue at position C-7 on the indole side chain. Subsequent modifications are catalyzed by modifying enzymes, but the mechanism by which this first step occurs is unknown. LodA possesses a cysteine tryptophylquinone (CTQ) cofactor. Metal analysis as well as spectroscopic and kinetic studies of the mature and precursor forms of a D512A LodA variant provides evidence that copper is required for the initial hydroxylation of the precursor protein and that if alternative metals are bound, the modification does not occur and the precursor is unstable...
February 21, 2017: Biochemistry
https://www.readbyqxmd.com/read/28128196/a-redox-neutral-catechol-synthesis
#16
Qian Wu, Dingyuan Yan, Ying Chen, Ting Wang, Feng Xiong, Wei Wei, Yi Lu, Wei-Yin Sun, Jie Jack Li, Jing Zhao
Ubiquitous tyrosinase catalyses the aerobic oxidation of phenols to catechols through the binuclear copper centres. Here, inspired by the Fischer indole synthesis, we report an iridium-catalysed tyrosinase-like approach to catechols, employing an oxyacetamide-directed C-H hydroxylation on phenols. This method achieves one-step, redox-neutral synthesis of catechols with diverse substituent groups under mild conditions. Mechanistic studies confirm that the directing group (DG) oxyacetamide acts as the oxygen source...
January 27, 2017: Nature Communications
https://www.readbyqxmd.com/read/28117677/in-vitro-dna-binding-anti-oxidant-and-anticancer-activity-of-indole-2-carboxylic-acid-dinuclear-copper-ii-complexes
#17
Xiangcong Wang, Maocai Yan, Qibao Wang, Huannan Wang, Zhengyang Wang, Jiayi Zhao, Jing Li, Zhen Zhang
Indole-2-carboxylic acid copper complex (ICA-Cu) was successfully prepared and characterized through elemental analysis, IR, UV-Vis, ¹H-NMR, TG analysis, and molar conductance, and its molecular formula was [Cu₂(C₉H₆O₂N)₄(H₂O)₂]·2H₂O. The binding ability of ICA-Cu to calf thymus DNA (CT-DNA) was examined by fluorescence spectrometry and the viscosity method. The results indicated that, upon the addition of increasing amounts of CT-DNA, the excitation and emission intensity of ICA-Cu decreased obviously and the excitation spectra shifted towards a long wavelength...
January 20, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28024187/synthesis-photophysical-properties-and-structures-of-organotin-schiff-bases-utilizing-aromatic-amino-acid-from-the-chiral-pool-and-evaluation-of-the-biological-perspective-of-a-triphenyltin-compound
#18
Tushar S Basu Baul, Pelesakuo Kehie, Andrew Duthie, Nikhil Guchhait, Nune Raviprakash, Raveendra B Mokhamatam, Sunil K Manna, Nerina Armata, Michelangelo Scopelliti, Ruimin Wang, Ulli Englert
Five new organotin(IV) complexes of compositions [Me2SnL(1)] (1), [Me2SnL(2)]n (2), [Me2SnL(3)] (3), [Ph3SnL(1)H]n (4) and [Ph3SnL(3)H] (5) (where L(1)=(2S)-2-((E)-((Z)-4-hydroxypent-3-en-2-ylidene)amino)-3-(1H-indol-3-yl)propanoate, L(2)=(2S)-(E)-2-((2-hydroxybenzylidene)amino)-3-(1H-indol-3-yl)propanoate and L(3)=(2S)-(E)-2-((1-(2-hydroxyphenyl)ethylidene)amino)-3-(1H-indol-3-yl)propanoate were synthesized and spectroscopically characterized. The crystal structures of 1-4 were determined. For the dimethyltin derivative 2, a polymeric chain structure was observed as a result of a long Sn∙∙∙O contact involving the exocyclic carbonyl oxygen-atom from the tridentate ligand of a neighboring Sn-complex unit...
December 16, 2016: Journal of Inorganic Biochemistry
https://www.readbyqxmd.com/read/28006917/monoterpene-indole-alkaloids-from-the-fruit-of-tabernaemontana-litoralis-and-differential-alkaloid-composition-in-various-fruit-components
#19
Yang Qu, Razvan Simonescu, Vincenzo De Luca
Two new monoterpene indole alkaloids, isoakuammiline (1) and 18-hydroxypseudovincadifformine (2), and five known alkaloids, coronaridine (3), heyneanine (4), 3,19-oxidocoronaridine (5), tabersonine, and strictosidine, were identified from the fruit of Tabernaemontana litoralis. The structures of the alkaloids were determined using NMR and MS data analyses. While 18-hydroxypseudovincadifformine (2) showed a new hydroxylation pattern, isoakuammiline (1) revealed a novel skeleton for monoterpene indole alkaloids...
December 23, 2016: Journal of Natural Products
https://www.readbyqxmd.com/read/27919656/biotransformation-of-isofraxetin-6-o-%C3%AE-d-glucopyranoside-by-angelica-sinensis-oliv-diels-callus
#20
Di Zhou, Yuhua Zhang, Zhe Jiang, Yue Hou, Kun Jiao, Chunyan Yan, Ning Li
Isofraxetin-6-O-β-d-glucopyranoside, identified from traditional medicinal herbal Xanthoceras sorbifolia Bunge, has been demonstrated to be a natural neuroinflammatory inhibitor. In order to obtain more derivatives with potential anti-neuroinflammatory effects, biotransformation was carried out. According to the characteristics of coumarin skeleton, suspension cultures of Angelica sinensis (Oliv.) Diels callus (A. sinensis callus) were employed because of the presence of diverse phenylpropanoids biosynthetic enzymes...
January 15, 2017: Bioorganic & Medicinal Chemistry Letters
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