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https://www.readbyqxmd.com/read/28221344/chemoproteomic-profiling-and-discovery-of-protein-electrophiles-in-human-cells
#1
Megan L Matthews, Lin He, Benjamin D Horning, Erika J Olson, Bruno E Correia, John R Yates, Philip E Dawson, Benjamin F Cravatt
Activity-based protein profiling (ABPP) serves as a chemical proteomic platform to discover and characterize functional amino acids in proteins on the basis of their enhanced reactivity towards small-molecule probes. This approach, to date, has mainly targeted nucleophilic functional groups, such as the side chains of serine and cysteine, using electrophilic probes. Here we show that 'reverse-polarity' (RP)-ABPP using clickable, nucleophilic hydrazine probes can capture and identify protein-bound electrophiles in cells...
March 2017: Nature Chemistry
https://www.readbyqxmd.com/read/28216563/the-genomic-impact-of-dna-cpg-methylation-on-gene-expression-relationships-in-prostate-cancer
#2
REVIEW
Mark D Long, Dominic J Smiraglia, Moray J Campbell
The process of DNA CpG methylation has been extensively investigated for over 50 years and revealed associations between changing methylation status of CpG islands and gene expression. As a result, DNA CpG methylation is implicated in the control of gene expression in developmental and homeostasis processes, as well as being a cancer-driver mechanism. The development of genome-wide technologies and sophisticated statistical analytical approaches has ushered in an era of widespread analyses, for example in the cancer arena, of the relationships between altered DNA CpG methylation, gene expression, and tumor status...
February 14, 2017: Biomolecules
https://www.readbyqxmd.com/read/28202018/de-novo-biosynthesis-of-pterostilbene-in-an-escherichia-coli-strain-using-a-new-resveratrol-o-methyltransferase-from-arabidopsis
#3
Kyung Taek Heo, Sun-Young Kang, Young-Soo Hong
BACKGROUND: Pterostilbene, a structural analog of resveratrol, has higher oral bioavailability and bioactivity than that of the parent compound; but is far less abundant in natural sources. Thus, to efficiently obtain this bioactive resveratrol analog, it is necessary to develop new bioproduction systems. RESULTS: We identified a resveratrol O-methyltransferase (ROMT) function from a multifunctional caffeic acid O-methyltransferase (COMT) originating from Arabidopsis, which catalyzes the transfer of a methyl group to resveratrol resulting in pterostilbene production...
February 15, 2017: Microbial Cell Factories
https://www.readbyqxmd.com/read/28167035/enzymatic-production-and-emission-of-floral-scent-volatiles-in-jasminum-sambac
#4
Paramita Bera, Chiranjit Mukherjee, Adinpunya Mitra
Floral scent composed of low molecular weight volatile organic compounds. The sweet fragrance of any evening blooming flower is dominated by benzenoid and terpenoid volatile compounds. Floral scent of Jasminum sambac (Oleaceae) includes three major benzenoid esters - benzylacetate, methylbenzoate, and methylsalicylate and three major terpene compounds viz. (E)-β-ocimene, linalool and α-farnesene. We analyzed concentrations and emission rates of benzenoids and terpenoids during the developmental stages of J...
March 2017: Plant Science: An International Journal of Experimental Plant Biology
https://www.readbyqxmd.com/read/28165739/discovery-of-novel-disruptor-of-silencing-telomeric-1-like-dot1l-inhibitors-using-a-target-specific-scoring-function-for-the-s-adenosyl-l-methionine-sam-dependent-methyltransferase-family
#5
Yulan Wang, Linjuan Li, Bidong Zhang, Jing Xing, Shijie Chen, Wei Wan, Yakai Song, Hao Jiang, Hualiang Jiang, Cheng Luo, Mingyue Zheng
The disruptor of telomeric silencing 1-like (DOT1L) protein is a histone H3K79 methyltransferase that plays a key role in transcriptional elongation and cell cycle regulation and is required for the development and maintenance of MLL-rearranged mixed lineage leukemia. Much effort has been dedicated toward discovering novel scaffold DOT1L inhibitors using different strategies. Here, we report the development and application of a target-specific scoring function, the SAM score, for (S)-adenosyl-l-methionine (SAM)-dependent methyltransferases, for the discovery of novel DOT1L inhibitors...
February 21, 2017: Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28152088/crystal-structure-and-catalytic-mechanism-of-couo-a-versatile-c-methyltransferase-from-streptomyces-rishiriensis
#6
Tea Pavkov-Keller, Kerstin Steiner, Mario Faber, Martin Tengg, Helmut Schwab, Mandana Gruber-Khadjawi, Karl Gruber
Friedel-Crafts alkylation of aromatic systems is a classic reaction in organic chemistry, for which regiospecific mono-alkylation, however, is generally difficult to achieve. In nature, methyltransferases catalyze the addition of methyl groups to a wide range of biomolecules thereby modulating the physico-chemical properties of these compounds. Specifically, S-adenosyl-L-methionine dependent C-methyltransferases possess a high potential to serve as biocatalysts in environmentally benign organic syntheses. Here, we report on the high resolution crystal structure of CouO, a C-methyltransferase from Streptomyces rishiriensis involved in the biosynthesis of the antibiotic coumermycin A1...
2017: PloS One
https://www.readbyqxmd.com/read/28140508/identifying-unknown-enzyme-substrate-pairs-from-the-cellular-milieu-with-native-mass-spectrometry
#7
Kalli C Catcott, Jing Yan, Wanlu Qu, Vicki H Wysocki, Zhaohui Sunny Zhou
The enzyme-substrate complex is inherently transient, rendering its detection difficult. In our framework, IsoLAIT (Isotope-Labeled, Activity-based Identification and Tracking), designed for bisubstrate systems, the common substrate, such as S-adenosyl-L-methionine (AdoMet) for methyltransferases, is replaced by an analogue (e.g., S-adenosyl-L-vinthionine) that, as a probe, creates a tightly bound [enzyme*substrate-probe] complex upon catalysis by thiopurine-S-methyltransferase (TPMT, EC 2.1.1.67). Then, this persistent complex is identified by native mass spectrometry from the cellular milieu without separation...
January 31, 2017: Chembiochem: a European Journal of Chemical Biology
https://www.readbyqxmd.com/read/28135697/colorimetric-detection-of-endogenous-hydrogen-sulfide-production-in-living-cells
#8
Yong Jin Ahn, Young Ju Lee, Jaemyeon Lee, Doyeon Lee, Hun-Kuk Park, Gi-Ja Lee
Hydrogen sulfide (H2S) has received great attention as a third gaseous signal transmitter, following nitric oxide and carbon monoxide. In particular, H2S plays an important role in the regulation of cancer cell biology. Therefore, the detection of endogenous H2S concentrations within biological systems can be helpful to understand the role of gasotransmitters in pathophysiology. Although a simple and inexpensive method for the detection of H2S has been developed, its direct and precise measurement in living cells remains a challenge...
January 22, 2017: Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
https://www.readbyqxmd.com/read/28125067/enniatin-and-beauvericin-biosynthesis-in-fusarium-species-production-profiles-and-structural-determinant-prediction
#9
Vania C Liuzzi, Valentina Mirabelli, Maria Teresa Cimmarusti, Miriam Haidukowski, John F Leslie, Antonio F Logrieco, Rocco Caliandro, Francesca Fanelli, Giuseppina Mulè
Members of the fungal genus Fusarium can produce numerous secondary metabolites, including the nonribosomal mycotoxins beauvericin (BEA) and enniatins (ENNs). Both mycotoxins are synthesized by the multifunctional enzyme enniatin synthetase (ESYN1) that contains both peptide synthetase and S-adenosyl-l-methionine-dependent N-methyltransferase activities. Several Fusarium species can produce ENNs, BEA or both, but the mechanism(s) enabling these differential metabolic profiles is unknown. In this study, we analyzed the primary structure of ESYN1 by sequencing esyn1 transcripts from different Fusarium species...
January 25, 2017: Toxins
https://www.readbyqxmd.com/read/28121423/noncoupled-fluorescent-assay-for-direct-real-time-monitoring-of-nicotinamide-n-methyltransferase-activity
#10
Harshini Neelakantan, Virginia Vance, Hua-Yu Leo Wang, Stanton F McHardy, Stanley J Watowich
Nicotinamide N-methyltransferase (NNMT) is an important biotransforming enzyme that catalyzes the transfer of a labile methyl group from the ubiquitous cofactor S-5'-adenosyl-l-methionine (SAM) to endogenous and exogenous small molecules to form methylated end products. NNMT has been implicated in a number of chronic disease conditions, including metabolic disorders, cardiovascular disease, cancer, osteoarthritis, kidney disease, and Parkinson's disease. We have developed a novel noncoupled fluorescence-based methyltransferase assay that allows direct ultrasensitive real-time detection of the NNMT reaction product 1-methylquinolinium...
January 30, 2017: Biochemistry
https://www.readbyqxmd.com/read/28095853/crispri-mediated-metabolic-engineering-of-e-coli-for-o-methylated-anthocyanin-production
#11
Brady F Cress, Quentin D Leitz, Daniel C Kim, Teresita D Amore, Jon Y Suzuki, Robert J Linhardt, Mattheos A G Koffas
BACKGROUND: Anthocyanins are a class of brightly colored, glycosylated flavonoid pigments that imbue their flower and fruit host tissues with hues of predominantly red, orange, purple, and blue. Although all anthocyanins exhibit pH-responsive photochemical changes, distinct structural decorations on the core anthocyanin skeleton also cause dramatic color shifts, in addition to improved stabilities and unique pharmacological properties. In this work, we report for the first time the extension of the reconstituted plant anthocyanin pathway from (+)-catechin to O-methylated anthocyanins in a microbial production system, an effort which requires simultaneous co-option of the endogenous metabolites UDP-glucose and S-adenosyl-L-methionine (SAM or AdoMet)...
January 17, 2017: Microbial Cell Factories
https://www.readbyqxmd.com/read/28074264/nacl-stress-induces-cssams-gene-expression-in-cucumis-sativus-by-mediating-the-binding-of-csgt-3b-to-the-gt-1-element-within-the-cssams-promoter
#12
Li-Wei Wang, Mei-Wen He, Shi-Rong Guo, Min Zhong, Sheng Shu, Jin Sun
The CsSAMs promoter is a salt-stress-inducible promoter containing three GT-1 elements that are sufficient for the salt-stress response. The transcription factor CsGT-3b was found to bind to the GT-1 element. The S-adenosyl-L-methionine synthase (SAMs) gene is among the functional genes induced during environmental stress. However, little is known about the regulatory mechanism and upstream regulators of this salt-inducible gene in cucumber plants. Thus, it is necessary to understand the characteristics of the SAMs gene by analyzing its promoter and transcription factors...
January 10, 2017: Planta
https://www.readbyqxmd.com/read/28068060/structural-and-functional-basis-of-c-methylation-of-coumarin-scaffolds-by-novo
#13
Joanna C Sadler, Chun-Wa H Chung, Julie E Mosley, Glenn A Burley, Luke D Humphreys
C-methylation of aromatic small molecules by C-methyltransferases (C-MTs) is an important biological transformation that involves C-C bond formation using S-adenosyl-l-methionine (SAM) as the methyl donor. Here, two advances in the mechanistic understanding of C-methylation of the 8-position of coumarin substrates catalyzed by the C-MT NovO from Streptomyces spheroides are described. First, a crystal structure of NovO reveals the Arg116-Asn117 and His120-Arg121 motifs are essential for coumarin substrate binding...
January 13, 2017: ACS Chemical Biology
https://www.readbyqxmd.com/read/28054779/n6-adenosine-dna-methyltransferase-from-h-pylori-98-10-strain-in-complex-with-dna-and-adomet-structural-insights-from-in-silico-studies
#14
Swati Singh, Lalitha Guruprasad
Helicobacter pylori is a primitive Gram-negative bacterium that resides in the acidic environment of the human gastrointestinal tract, and some strains of this bacterium cause gastric ulcers and cancer. DNA methyltransferases (MTases) are promising drug targets for the treatment of cancer and other diseases that are also caused by epigenetic alternations of the genome. The N6-adenine-specific DNA MTase from H. pylori (M. Hpy N6mA) catalyzes the transfer of a methyl group from the cofactor S-adenosyl-l-methionine (AdoMet) to the flipped adenine of the substrate DNA...
January 19, 2017: Journal of Physical Chemistry. B
https://www.readbyqxmd.com/read/28045519/7-carboxy-7-deazaguanine-synthase-a-radical-s-adenosyl-l-methionine-enzyme-with-polar-tendencies
#15
Nathan A Bruender, Tsehai A J Grell, Daniel P Dowling, Reid M McCarty, Catherine L Drennan, Vahe Bandarian
Radical S-adenosyl-l-methionine (SAM) enzymes are widely distributed and catalyze diverse reactions. SAM binds to the unique iron atom of a site-differentiated [4Fe-4S] cluster and is reductively cleaved to generate a 5'-deoxyadenosyl radical, which initiates turnover. 7-Carboxy-7-deazaguanine (CDG) synthase (QueE) catalyzes a key step in the biosynthesis of 7-deazapurine containing natural products. 6-Carboxypterin (6-CP), an oxidized analogue of the natural substrate 6-carboxy-5,6,7,8-tetrahydropterin (CPH4), is shown to be an alternate substrate for CDG synthase...
February 8, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28042932/novel-adomet-analogues-as-tools-for-enzymatic-transfer-of-photo-crosslinkers-and-capturing-rna-protein-interactions
#16
Fabian Muttach, Florain Mäsing, Armido Studer, Andrea Rentmeister
Elucidation of biomolecular interactions is of utmost importance in biochemistry. Photo-crosslinking offers the possibility to precisely determine RNA-protein interactions. However, despite the inherent specificity of enzymes, approaches for site-specific introduction of photo-crosslinking moieties into nucleic acids are scarce. Methyltransferases in combination with synthetic analogues of their natural cosubstrate S-adenosyl-L-methionine (AdoMet) allow for the post-synthetic site-specific modification of biomolecules...
January 2, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28031456/a-novel-motif-for-s-adenosyl-l-methionine-binding-by-the-ribosomal-rna-methyltransferase-tlya-from-mycobacterium-tuberculosis
#17
Marta A Witek, Emily G Kuiper, Elizabeth Minten, Emily K Crispell, Graeme L Conn
Capreomycin is a potent ribosome-targeting antibiotic that is an essential component of current antituberculosis treatments, particularly in the case of multidrug-resistant Mycobacterium tuberculosis (Mtb). Optimal capreomycin binding and Mtb ribosome inhibition requires ribosomal RNA methylation in both ribosome subunits by TlyA (Rv1694), an enzyme with dual 2'-O-methytransferase and putative hemolytic activities. Despite the important role of TlyA in capreomycin sensitivity and identification of inactivating mutations in the corresponding Mtb gene tlyA, which cause resistance to capreomycin, our current structural and mechanistic understanding of TlyA action remains limited...
February 3, 2017: Journal of Biological Chemistry
https://www.readbyqxmd.com/read/28031370/binding-of-the-methyl-donor-s-adenosyl-l-methionine-to-middle-east-respiratory-syndrome-coronavirus-2-o-methyltransferase-nsp16-promotes-recruitment-of-the-allosteric-activator-nsp10
#18
Wahiba Aouadi, Alexandre Blanjoie, Jean-Jacques Vasseur, Françoise Debart, Bruno Canard, Etienne Decroly
The Middle East respiratory syndrome coronavirus (MERS-CoV) nonstructural protein 16 (nsp16) is an S-adenosyl-l-methionine (SAM)-dependent 2'-O-methyltransferase (2'-O-MTase) that is thought to methylate the ribose 2'-OH of the first transcribed nucleotide (N1) of viral RNA cap structures. This 2'-O-MTase activity is regulated by nsp10. The 2'-O methylation prevents virus detection by cell innate immunity mechanisms and viral translation inhibition by the interferon-stimulated IFIT-1 protein. To unravel the regulation of nsp10/nsp16 2'-O-MTase activity, we used purified MERS-CoV nsp16 and nsp10...
March 1, 2017: Journal of Virology
https://www.readbyqxmd.com/read/28027411/dna-repair-by-the-radical-sam-enzyme-spore-photoproduct-lyase-from-biochemistry-to-structural-investigations
#19
REVIEW
Olivier Berteau, Alhosna Benjdia
Radical S-adenosyl-L-methionine (SAM) enzymes have emerged as one of the last superfamilies of enzymes discovered to date. Arguably, it is the most versatile group of enzymes involved in at least 85 biochemical transformations. One of the founding members of this enzyme superfamily is the spore photoproduct (SP) lyase, a DNA repair enzyme catalyzing the direct reversal repair of a unique DNA lesion, the so-called spore photoproduct, back into two thymidine residues. Discovered more than 20 years ago in the bacterium Bacillus subtilis, SP lyase has been shown to be widespread in the endospore-forming Firmicutes from the Bacilli and Clostridia classes and to use radical-based chemistry to perform C-C bond breakage, a chemically challenging reaction...
December 27, 2016: Photochemistry and Photobiology
https://www.readbyqxmd.com/read/28003820/feasibility-and-efficacy-of-s-adenosyl-l-methionine-in-patients-with-hbv-related-hcc-with-different-bclc-stages
#20
Tao Guo, Yukun He, Weijie Ma, Zhisu Liu, Quanyan Liu
Aims. To understand the feasibility and efficacy of treatment with SAMe in patients with hepatitis B-related HCC with different Barcelona Clinic Liver Cancer (BCLC) stages. Methods. We retrospectively enrolled 697 patients with BCLC early-stage (stages 0-A) and advanced-stage (stages B-C) HCC who underwent SAMe therapy (354 cases) or no SAMe therapy (343 cases). The baseline characteristics, postoperative recoveries, and 24-month overall survival rates of the patients in the 2 groups were compared. Cox regression model analysis was performed to confirm the independent variables influencing the survival rate...
2016: Gastroenterology Research and Practice
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