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Peppi Koivunen, Johanna Myllyharju
Kinetic analyses of HIF prolyl 4-hydroxylases (HIF-P4Hs) allow determination of substrate, cosubstrate and cofactor requirements, analysis of the reaction rate, and inhibitory properties of the isoenzymes in vitro. Here we describe an assay measuring the substrate hydroxylation-coupled decarboxylation of radioactive 2-oxoglutarate to radioactive carbon dioxide as a fast, efficient, and diverse method to analyze the enzyme kinetics of HIF-P4Hs.
2018: Methods in Molecular Biology
Seokjung Cheong, James M Clomburg, Ramon Gonzalez
Synthetic biology, encompassing the design and construction of novel artificial biological pathways and organisms and the redesign of existing natural biological systems, is rapidly expanding the number of applications for which biological systems can play an integral role. In the context of chemical production, the combination of synthetic biology and metabolic engineering approaches continues to unlock the ability to biologically produce novel and complex molecules from a variety of feedstocks. Here, we utilize a synthetic approach to design and build a pathway to produce 2-hydroxyisovaleric acid in Escherichia coli and demonstrate how pathway design can be supplemented with metabolic engineering approaches to improve pathway performance from various carbon sources...
January 12, 2018: Journal of Industrial Microbiology & Biotechnology
Scott Bottoms, Quinn Dickinson, Mick McGee, Li Hinchman, Alan Higbee, Alex Hebert, Jose Serate, Dan Xie, Yaoping Zhang, Joshua J Coon, Chad L Myers, Robert Landick, Jeff S Piotrowski
BACKGROUND: Gamma valerolactone (GVL) treatment of lignocellulosic bomass is a promising technology for degradation of biomass for biofuel production; however, GVL is toxic to fermentative microbes. Using a combination of chemical genomics with the yeast (Saccharomyces cerevisiae) deletion collection to identify sensitive and resistant mutants, and chemical proteomics to monitor protein abundance in the presence of GVL, we sought to understand the mechanism toxicity and resistance to GVL with the goal of engineering a GVL-tolerant, xylose-fermenting yeast...
January 12, 2018: Microbial Cell Factories
Anirudra Paul, N R Thimmegowda, Thiago Galani Cruz, Daniel Seidel
Indolizidine and quinolizidine derivatives are readily assembled from l-proline or (±)-pipecolic acid and β-ketoaldehydes via a decarboxylative annulation process. These reactions are promoted by acetic acid and involve azomethine ylides as reactive intermediates.
January 12, 2018: Organic Letters
Cristina Izquierdo, José C Gómez-Tamayo, Jean-Christophe Nebel, Leonardo Pardo, Angel Gonzalez
Pungent chemical compounds originating from decaying tissue are strong drivers of animal behavior. Two of the best-characterized death smell components are putrescine (PUT) and cadaverine (CAD), foul-smelling molecules produced by decarboxylation of amino acids during decomposition. These volatile polyamines act as 'necromones', triggering avoidance or attractive responses, which are fundamental for the survival of a wide range of species. The few studies that have attempted to identify the cognate receptors for these molecules have suggested the involvement of the seven-helix trace amine-associated receptors (TAARs), localized in the olfactory epithelium...
January 11, 2018: PLoS Computational Biology
Chenglong Wang, Jingyi Qiao, Xiaochong Liu, He Song, Zhizhong Sun, Wenyi Chu
A visible-light-induced decarboxylation coupling /intramolecular cyclization is reported. The one-pot synthesis system provides mild, efficient and atom economical access to the synthesis of 4-aryl-2-quinolinone derivatives. It is notable that the necessary oxidant in the traditional decarboxylation coupling is replaced by the visible-light-irradiation in this paper. In addition, the HBV inhibitor is synthesized by the one-pot synthesis system in an atom economical manner.
January 11, 2018: Journal of Organic Chemistry
Arif Luqman, Mulugeta Nega, Minh-Thu Nguyen, Patrick Ebner, Friedrich Götz
A subgroup of biogenic amines, the so-called trace amines (TAs), are produced by mammals and bacteria and can act as neuromodulators. In the genus Staphylococcus, certain species are capable of producing TAs through the activity of staphylococcal aromatic amino acid decarboxylase (SadA). SadA decarboxylates aromatic amino acids to produce TAs, as well as dihydroxy phenylalanine and 5-hydroxytryptophan to thus produce the neurotransmitters dopamine and serotonin. SadA-expressing staphylococci were prevalent in the gut of most probands, where they are part of the human intestinal microflora...
January 9, 2018: Cell Reports
Adam Noble, Riccardo S Mega, Daniel Pflästerer, Eddie L Myers, Varinder Kumar Aggarwal
The synthesis of alkyl boronic esters by direct decarboxylative radical addition of carboxylic acids to vinyl boronic esters is described. The reaction proceeds under mild photoredox catalysis and involves an unprecedented single-electron reduction of an α-boryl radical intermediate to the corresponding anion. The reaction is amenable to a diverse range of substrates, including α-amino, α-oxy, and alkyl carboxylic acids, thus providing a novel method to rapidly access boron-containing molecules of potential biological importance...
January 8, 2018: Angewandte Chemie
Hong Fu, Jia-Qi Shang, Tao Yang, Yuehai Shen, Chuan-Zhu Gao, Ya-Min Li
A copper-catalyzed decarboxylative disulfonylation of alkynyl carboxylic acids with sulfinic acids in aqueous solution has been developed. The reaction provides a straightforward and practical access to (E)-1,2-disulfonylethenes, which are important building blocks in synthetic organic chemistry, and exhibits a good functional group tolerance and excellent stereoselectivity. A possible mechanism for the transformation is proposed.
January 9, 2018: Organic Letters
Greg Springsteen, Jayasudhan Reddy Yerabolu, Julia Nelson, Chandler Joel Rhea, Ramanarayanan Krishnamurthy
The development of metabolic approaches towards understanding the origins of life, which have focused mainly on the citric acid (TCA) cycle, have languished-primarily due to a lack of experimentally demonstrable and sustainable cycle(s) of reactions. We show here the existence of a protometabolic analog of the TCA involving two linked cycles, which convert glyoxylate into CO2 and produce aspartic acid in the presence of ammonia. The reactions proceed from either pyruvate, oxaloacetate or malonate in the presence of glyoxylate as the carbon source and hydrogen peroxide as the oxidant under neutral aqueous conditions and at mild temperatures...
January 8, 2018: Nature Communications
Kai Chen, Yang Mu, Shanshan Jian, Xiaoxia Zang, Qing Chen, Weibin Jia, Zhuang Ke, Yanzheng Gao, Jiandong Jiang
The compound 3,5-dibromo-4-hydroxybenzoate (DBHB) is both anthropogenically released into and naturally produced in the environment, and its environmental fate is of great concern. Aerobic and anaerobic reductive dehalogenations are the only two reported pathways for DBHB catabolism. In this study, a new oxidative-decarboxylation pathway for DBHB catabolism was identified in a DBHB-utilizing strain of Pigmentiphaga sp. H8. The genetic determinants underlying this pathway were elucidated based on comparative transcriptome analysis and subsequent experimental validation...
January 5, 2018: Applied and Environmental Microbiology
Jarett Wilcoxen, Nathan A Bruender, Vahe Bandarian, R David Britt
7-Carboxy-7-deazaguanine (CDG) synthase (QueE), a member of the radical S-deoxyadenosyl-L-methionine (SAM) superfamily of enzymes, catalyzes a radical-mediated ring rearrangement required to convert 6-carboxy-5,6,7,8-tetrahydropterin (CPH4) into CDG, forming the 7-dezapurine precursor to all pyrrolopyrimidine metabolites. Members of the radical SAM superfamily bind SAM to a [4Fe-4S] cluster, leveraging the reductive cleavage of SAM by the cluster to produce a highly reactive 5-deoxyadenosyl radical which initiates chemistry by H-atom abstraction from the substrate...
January 5, 2018: Journal of the American Chemical Society
Weiguang Kong, Changjiang Yu, Hejun An, Qiuling Song
Photoredox-catalyzed decarboxylative alkylation of silyl enol ethers has been developed. Diverse functionalized aryl alkyl ketones were afforded in modest to good yields using N-(acyloxy)phthalimide as an easy access alkyl radical source under mild and operationally simple conditions. The excellent performance of drug molecules such as fenbufen and indomethacin and naturally occurring carboxylic acids such as stearic acid and dehydrocholic acid further demonstrated the practicability of the reaction.
January 4, 2018: Organic Letters
Jun-Cheng Yang, Jia-Yu Zhang, Jin-Jiang Zhang, Xin-Hua Duan, Li-Na Guo
A visible-light mediated decarboxylative cyclization of N-Acyloxylphthalimides with vinyl azides has been developed under metal-free conditions. This protocol features mild conditions, broad substrate scope and excellent functional group tolerance, thus providing a facile and efficient access to substituted phenanthridines. Control experiments revealed that the reaction proceeded via a radical process.
January 4, 2018: Journal of Organic Chemistry
Nicolas Lespes, Etienne Pair, Clisy Maganga, Marie Bretier, Vincent Tognetti, Laurent Joubert, Vincent Levacher, Marie Hubert-Roux, Carlos Afonso, Corinne Loutelier-Bourhis, Jean-François Brière
The fragile intermediates of the domino process leading to isoxazolidin-5-one, triggered by the unique reactivity between Meldrum's acid and N-Bn nitrone in the presence of a Brønsted base, were determined thanks to the softness and accuracy of electrospray ionization mass spectrometry coupled to ion mobility spectrometry (ESI-IMS-MS). The combined DFT study shed light on the overall organocatalytic sequence, which starts by a stepwise (3+2) annulation reaction followed by a decarboxylative protonation sequence encompassing a stereoselective pathway issue...
January 3, 2018: Chemistry: a European Journal
Nupam P Mahajan, Pavani Malla, Shambhavi Bhagwat, Vasundhara Sharma, Amod Sarnaik, Jongphil Kim, Shari Pilon-Thomas, Jeffery Weber, Kiran Mahajan
Epigenetic signaling networks dynamically regulate gene expression to maintain cellular homeostasis. Previously, we uncovered that WEE1 phosphorylates histone H2B at tyrosine 37 (pY37-H2B) to negatively regulate global histone transcriptional output. Although pY37-H2B is readily detected in cancer cells, its functional role in pathogenesis is not known. Herein, we show that WEE1 deposits the pY37-H2B marks within the tumor suppressor gene, isocitrate dehydrogenase 2 (IDH2), to repress transcription in multiple cancer cells, including glioblastoma multiforme (GBMs), melanoma and prostate cancer...
December 5, 2017: Oncotarget
Yulan Yu, Weiwen Yuan, Hansheng Huang, Zhiqiang Cai, Ping Liu, Peipei Sun
The visible light-mediated decarboxylative functionalization of aliphatic carboxylic acids using organocatalysts has rarely been reported. This study represented an environmentally benign decarboxylation method involving the combination of eosin Y and (NH4)2S2O8. This system converted aliphatic carboxylic acids to alkyl radicals, followed by their addition to the carbon-carbon double bond of N-arylacrylamides cascade cyano insertion/cyclization to construct alkylated phenanthridines in moderate to good yields under photoredox catalysis...
December 29, 2017: Journal of Organic Chemistry
Xiang Sheng, Yury Patskovsky, Anna Vladimirova, Jeffrey B Bonanno, Steven C Almo, Fahmi Himo, Frank M Raushel
γ-Resorcylate decarboxylase (γ-RSD) has evolved to catalyze the reversible decarboxylation of 2,6-dihydroxybenzoate to resorcinol in a nonoxidative fashion. This enzyme is of significant interest because of its potential for the production of γ-resorcylate and other benzoic acid derivatives under environmentally sustainable conditions. Kinetic constants for the decarboxylation of 2,6-dihydroxybenzoate catalyzed by γ-RSD from Polaromonas sp. JS666 are reported and the enzyme is shown to be active with 2,3-dihydroxybenzoate, 2,4,6-trihydroxybenzoate and 2,6-dihydroxy-4 methylbenzoate...
December 28, 2017: Biochemistry
Filipe C Pikart, Mauro A Marabesi, Paulo T Mioto, Ana Z Gonçalves, Alejandra Matiz, Frederico R R Alves, Helenice Mercier, Marcos P M Aidar
The Crassulacean acid metabolism (CAM) can be a transitory strategy for saving water during unfavourable conditions, like a dry season. In some cases, CAM can also contribute to the maintenance of photosynthetic integrity, even if carbon gain and growth are impaired. CAM occurs in different intensities, being stronger or weaker depending on the degree of nocturnal malic acid accumulation. For example, Guzmania monostachia is an epiphytic tank bromeliad that shows an increase in its nocturnal organic acid accumulation and a variable CAM behaviour when exposed to water deficit...
December 19, 2017: Plant Physiology and Biochemistry: PPB
Bing Huang, Hao Yang, Guochen Fang, Xing Zhang, Hui Wu, Zhimin Li, Qin Ye
Acetate, a non-food based substrate obtained from multiple biological and chemical ways, is now being paid great attention in bio-manufacturing and have a strong potential to compete with sugar-based carbon source. In this study, acetate can be efficiently converted to succinate by engineered Escherichia coli strains via the combination of several metabolic engineering strategies, including reducing OAA decarboxylation, engineering TCA cycle, enhancement of acetate assimilation pathway and increasing aerobic ATP supply through cofactor engineering...
December 26, 2017: Biotechnology and Bioengineering
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