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polyketide synthase

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https://www.readbyqxmd.com/read/28430424/elucidation-of-the-stereospecificity-of-c-methyltransferases-from-trans-at-polyketide-synthases
#1
Xinqiang Xie, Chaitan Khosla, David E Cane
S-Adenosyl methionine (SAM)-dependent C-methyltransferases are responsible for the C2-methylation of 3-ketoacyl-acyl carrier protein (ACP) intermediates to give the corresponding 2-methy-3-ketoacyl-ACP products during bacterial polyketide biosynthesis mediated by trans-AT polyketide synthases that lack integrated acyl transferase (AT) domains. A coupled ketoreductase (KR) assay was used to assign the stereochemistry of the C-methyltransferase-catalyzed reaction. Samples of chemoenzymatically-generated 3-ketopentanoyl-ACP (9) were incubated with SAM and BonMT2 from module 2 of the bongkrekic acid polyke-tide synthase...
April 21, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28427010/leveraging-microbial-biosynthetic-pathways-for-the-generation-of-drop-in-biofuels
#2
REVIEW
Amin Zargar, Constance B Bailey, Robert W Haushalter, Christopher B Eiben, Leonard Katz, Jay D Keasling
Advances in retooling microorganisms have enabled bioproduction of 'drop-in' biofuels, fuels that are compatible with existing spark-ignition, compression-ignition, and gas-turbine engines. As the majority of petroleum consumption in the United States consists of gasoline (47%), diesel fuel and heating oil (21%), and jet fuel (8%), 'drop-in' biofuels that replace these petrochemical sources are particularly attractive. In this review, we discuss the application of aldehyde decarbonylases to produce gasoline substitutes from fatty acid products, a recently crystallized reductase that could hydrogenate jet fuel precursors from terpene synthases, and the exquisite control of polyketide synthases to produce biofuels with desired physical properties (e...
April 17, 2017: Current Opinion in Biotechnology
https://www.readbyqxmd.com/read/28422496/the-combined-use-of-proteomics-and-transcriptomics-reveals-a-complex-secondary-metabolite-network-in-peperomia-obtusifolia
#3
Andrea N L Batista, José Roberto A Dos Santos-Pinto, João M Batista, Tatiana M Souza-Moreira, Mariana M Santoni, Cleslei F Zanelli, Massuo J Kato, Silvia N López, Mario S Palma, Maysa Furlan
Peperomia obtusifolia, an ornamental plant from the Piperaceae family, accumulates a series of secondary metabolites with interesting biological properties. From a biosynthesis standpoint, this species produces several benzopyrans derived from orsellinic acid, which is a polyketide typically found in fungi. Additionally, the chiral benzopyrans were reported as racemic and/or as diastereomeric mixtures, which raises questions about the level of enzymatic control in the cyclization step for the formation of the 3,4-dihydro-2H-pyran moiety...
April 19, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28418225/an-iterative-module-in-the-azalomycin%C3%A2-f-polyketide-synthase-contains-a-switchable-enoylreductase-domain
#4
Wei Xu, Guifa Zhai, Yuanzhen Liu, Yuan Li, Yanrong Shi, Kui Hong, Hui Hong, Peter F Leadlay, Zixin Deng, Yuhui Sun
Detailed analysis of the modular Type I polyketide synthase (PKS) involved in the biosynthesis of the marginolactone azalomycin F in mangrove Streptomyces sp. 211726 has shown that only nineteen extension modules are required to accomplish twenty cycles of polyketide chain elongation. Analysis of the products of a PKS mutant specifically inactivated in the dehydratase domain of extension-module 1 showed that this module catalyzes two successive elongations with different outcomes. Strikingly, the enoylreductase domain of this module can apparently be "toggled" off and on : it functions in only the second of these two cycles...
April 18, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28411241/2-alkylquinolone-alkaloid-biosynthesis-in-the-medicinal-plant-evodia-rutaecarpa-involves-collaboration-of-two-novel-type-iii-polyketide-synthases
#5
Takashi Matsui, Takeshi Kodama, Takahiro Mori, Tetsuhiro Tadakoshi, Hiroshi Noguchi, Ikuro Abe, Hiroyuki Morita
2-Alkylquinolone (2AQ) alkaloids are pharmaceutically and biologically important natural products produced by both bacteria and plants, with a wide range of biological effects, including antibacterial, cytotoxic, anticholinesterase, and quorum-sensing signaling activities. These diverse activities and 2AQ occurrence in vastly different phyla have raised much interest in the biosynthesis pathways leading to their production. Previous studies in plants have suggested that type III polyketide synthases (PKSs) might be involved in 2AQ biosynthesis, but this hypothesis is untested...
April 14, 2017: Journal of Biological Chemistry
https://www.readbyqxmd.com/read/28394118/the-uncommon-enzymology-of-cis-acyltransferase-assembly-lines
#6
Adrian T Keatinge-Clay
The enzymology of 135 assembly lines containing primarily cis-acyltransferase modules is comprehensively analyzed, with greater attention paid to less common phenomena. Diverse online transformations, in which the substrate and/or product of the reaction is an acyl chain bound to an acyl carrier protein, are classified so that unusual reactions can be compared and underlying assembly-line logic can emerge. As a complement to the chemistry surrounding the loading, extension, and offloading of assembly lines that construct primarily polyketide products, structural aspects of the assembly-line machinery itself are considered...
April 10, 2017: Chemical Reviews
https://www.readbyqxmd.com/read/28393528/one-step-transformation-of-coenzyme-a-into-analogues-by-transamidation
#7
Randy Sanichar, John C Vederas
Several coenzyme A (CoA) analogues are made in a single step under mild conditions via transamidation reactions catalyzed by boric acid in water. This approach offers rapid access to compounds useful for the study of a wide spectrum of enzyme catalyzed reactions, especially processes involving acyl carrier proteins (ACP) of polyketide synthases (PKS), fatty acid synthases (FAS), and nonribosomal peptide synthetases (NRPS). The CoA analogues presented are readily elaborated or extended by precedented reactions for specific applications that may be required...
April 10, 2017: Organic Letters
https://www.readbyqxmd.com/read/28383583/new-insights-into-polyene-macrolide-biosynthesis-in-couchioplanes-caeruleus
#8
J Sheehan, C D Murphy, P Caffrey
Couchioplanes caeruleus DSM43634 synthesises 67-121C, an aromatic heptaene macrolide that contains a mannosyl-mycosaminyl disaccharide. An improved draft genome sequence was used to obtain the biosynthetic gene cluster for this antifungal. Bioinformatic analysis of the polyketide synthase indicated that extension modules 7 and 8 contain A-type ketoreductase and dehydratase domains. These modules are therefore predicted to form cis double bonds. The deduced stereostructure of the 67-121C macrolactone is identical to that experimentally determined for the partricin subgroup of aromatic heptaenes...
April 6, 2017: Molecular BioSystems
https://www.readbyqxmd.com/read/28379953/aspergillus-hancockii-sp-nov-a-biosynthetically-talented-fungus-endemic-to-southeastern-australian-soils
#9
John I Pitt, Lene Lange, Alastair E Lacey, Daniel Vuong, David J Midgley, Paul Greenfield, Mark I Bradbury, Ernest Lacey, Peter K Busk, Bo Pilgaard, Yit-Heng Chooi, Andrew M Piggott
Aspergillus hancockii sp. nov., classified in Aspergillus subgenus Circumdati section Flavi, was originally isolated from soil in peanut fields near Kumbia, in the South Burnett region of southeast Queensland, Australia, and has since been found occasionally from other substrates and locations in southeast Australia. It is phylogenetically and phenotypically related most closely to A. leporis States and M. Chr., but differs in conidial colour, other minor features and particularly in metabolite profile. When cultivated on rice as an optimal substrate, A...
2017: PloS One
https://www.readbyqxmd.com/read/28377293/insights-into-substrate-modification-by-dehydratases-from-type-i-polyketide-synthases
#10
Alexandre Faille, Sabine Gavalda, Nawel Slama, Christian Lherbet, Laurent Maveyraud, Valérie Guillet, Françoise Laval, Annaïk Quémard, Lionel Mourey, Jean-Denis Pedelacq
Dehydration reactions play a crucial role for de novo biosynthesis of fatty acids and a wide range of pharmacologically active polyketide natural products with strong emphasis in human medicine. The type I polyketide synthase PpsC from Mycobacterium tuberculosis catalyzes key biosynthetic steps of lipid virulence factors phthiocerol dimycocerosates (DIM) and phenolic glycolipids (PGL). Given the insolubility of the natural C28-C30 fatty acyl substrate of the PpsC DH domain, we investigated its structure-function relationships in the presence of shorter surrogate substrates...
April 1, 2017: Journal of Molecular Biology
https://www.readbyqxmd.com/read/28368369/global-analysis-of-biosynthetic-gene-clusters-reveals-vast-potential-of-secondary-metabolite-production-in-penicillium-species
#11
Jens Christian Nielsen, Sietske Grijseels, Sylvain Prigent, Boyang Ji, Jacques Dainat, Kristian Fog Nielsen, Jens Christian Frisvad, Mhairi Workman, Jens Nielsen
Filamentous fungi produce a wide range of bioactive compounds with important pharmaceutical applications, such as antibiotic penicillins and cholesterol-lowering statins. However, less attention has been paid to fungal secondary metabolites compared to those from bacteria. In this study, we sequenced the genomes of 9 Penicillium species and, together with 15 published genomes, we investigated the secondary metabolism of Penicillium and identified an immense, unexploited potential for producing secondary metabolites by this genus...
April 3, 2017: Nature Microbiology
https://www.readbyqxmd.com/read/28366630/identification-and-functional-characterization-of-three-type-iii-polyketide-synthases-from-aquilaria-sinensis-calli
#12
Xiaohui Wang, Zhongxiu Zhang, Xianjuan Dong, Yingying Feng, Xiao Liu, Bowen Gao, Jinling Wang, Le Zhang, Juan Wang, Shepo Shi, Pengfei Tu
Type III polyketide synthases (PKSs) play an important role in biosynthesis of various plant secondary metabolites and plant adaptation to environmental stresses. Aquilaria sinensis is the main plant species for production of agarwood, little is known about the PKS family. In this study, AsCHS1 and two new type III PKSs, AsPKS1 and AsPKS2, were isolated and characterized in Aquilaria sinensis calli. The comparative sequence and phylogenetic analysis indicated that AsPKS1 and AsPKS2 belong to non-CHS group different from AsCHS1...
March 30, 2017: Biochemical and Biophysical Research Communications
https://www.readbyqxmd.com/read/28365998/collaborative-biosynthesis-of-maleimide-and-succinimide-containing-natural-products-by-fungal-polyketide-megasynthases
#13
Michio Sato, Jacob E Dander, Chizuru Sato, Yiu-Sun Hung, Shu-Shan Gao, Man-Cheng Tang, Leibniz Hang, Jaclyn M Winter, Neil K Garg, Kenji Watanabe, Yi Tang
Fungal polyketide synthases (PKSs) can function collaboratively to synthesize natural products of significant structural diversity. Here we present a new mode of collaboration between a highly reducing PKS (HRPKS) and a PKS-nonribosomal peptide synthetase (PKS-NRPS) in the synthesis of oxaleimides from the Penicillium species. The HRPKS is recruited in the synthesis of an olefin-containing free amino acid, which is activated and incorporated by the adenylation domain of the PKS-NRPS. The precisely positioned olefin from the unnatural amino acid is proposed to facilitate a scaffold rearrangement of the PKS-NRPS product to forge the maleimide and succinimide cores of oxaleimides...
April 5, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28352091/genome-sequencing-and-analysis-of-talaromyces-pinophilus-provide-insights-into-biotechnological-applications
#14
Cheng-Xi Li, Shuai Zhao, Ting Zhang, Liang Xian, Lu-Sheng Liao, Jun-Liang Liu, Jia-Xun Feng
Species from the genus Talaromyces produce useful biomass-degrading enzymes and secondary metabolites. However, these enzymes and secondary metabolites are still poorly understood and have not been explored in depth because of a lack of comprehensive genetic information. Here, we report a 36.51-megabase genome assembly of Talaromyces pinophilus strain 1-95, with coverage of nine scaffolds of eight chromosomes with telomeric repeats at their ends and circular mitochondrial DNA. In total, 13,472 protein-coding genes were predicted...
March 28, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28334262/discriminating-the-reaction-types-of-plant-type-iii-polyketide-synthases
#15
Yugo Shimizu, Hiroyuki Ogata, Susumu Goto
Motivation: Functional prediction of paralogs is challenging in bioinformatics because of rapid functional diversification after gene duplication events combined with parallel acquisitions of similar functions by different paralogs. Plant type III polyketide synthases (PKSs), producing various secondary metabolites, represent a paralogous family that has undergone gene duplication and functional alteration. Currently, there is no computational method available for the functional prediction of type III PKSs...
March 6, 2017: Bioinformatics
https://www.readbyqxmd.com/read/28331973/green-fluorescent-protein-as-a-reporter-for-the-spatial-and-temporal-expression-of-actiii-in-streptomyces-coelicolor
#16
Fernando Santos-Beneit, Jeff Errington
Polyketides constitute a large group of structurally diverse natural products with useful biological activities. Insights into their biosynthetic mechanisms are crucial for developing new structures. One of the most studied model polyketide is the blue-pigmented antibiotic actinorhodin, produced by Streptomyces coelicolor. This aromatic polyketide is synthesized by minimal type II polyketide synthases and tailoring enzymes. The ActIII actinorhodin ketoreductase is a key tailoring enzyme in actinorhodin biosynthesis...
March 22, 2017: Archives of Microbiology
https://www.readbyqxmd.com/read/28326787/linear-peptides-are-the-major-products-of-a-biosynthetic-pathway-that-encodes-for-cyclic-depsipeptides
#17
Thomas P Wyche, Antonio C Ruzzini, Christine Beemelmanns, Ki Hyun Kim, Jonathan L Klassen, Shugeng Cao, Michael Poulsen, Tim S Bugni, Cameron R Currie, Jon Clardy
Three new dentigerumycin analogues are produced by Streptomyces sp. M41, a bacterium isolated from a South African termite, Macrotermes natalensis. The structures of the complex nonribosomal peptide synthetase-polyketide synthase (NRPS/PKS) hybrid compounds were determined by 1D- and 2D-NMR spectroscopy, high-resolution mass spectrometry, and circular dichroism (CD) spectroscopy. Both cyclic and linear peptides are reported, and the genetic organization of the NRPS modules within the biosynthetic gene cluster accounts for the observed structural diversity...
April 7, 2017: Organic Letters
https://www.readbyqxmd.com/read/28326145/polyketide-stereocontrol-a-study-in-chemical-biology
#18
REVIEW
Kira J Weissman
The biosynthesis of reduced polyketides in bacteria by modular polyketide synthases (PKSs) proceeds with exquisite stereocontrol. As the stereochemistry is intimately linked to the strong bioactivity of these molecules, the origins of stereochemical control are of significant interest in attempts to create derivatives of these compounds by genetic engineering. In this review, we discuss the current state of knowledge regarding this key aspect of the biosynthetic pathways. Given that much of this information has been obtained using chemical biology tools, work in this area serves as a showcase for the power of this approach to provide answers to fundamental biological questions...
2017: Beilstein Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28322927/pathogenic-and-immunosuppressive-properties-of-mycobacterial-phenolic-glycolipids
#19
Reid Oldenburg, Caroline Demangel
Phenolic glycolipids (PGL) are polyketide synthase products that are uniquely produced by a subset of pathogenic mycobacteria and are displayed at the bacterial cell surface, in a strategic position to interfere with host immune cells. Their expression has been associated with enhanced mycobacterial virulence in vivo, and suppression of the inflammatory responses of host phagocytes in vitro. In this review, we will present our current understanding of the mode of operation of PGL, along with functional evidence that demonstrates the evolutionary advantage conferred by PGL production for host cell invasion, intracellular persistence and evasion of host immune and bactericidal responses...
March 18, 2017: Biochimie
https://www.readbyqxmd.com/read/28322495/polyketide-synthase-modules-redefined
#20
Adrian T Keatinge-Clay
Modular redefinition: A long-standing paradigm in modular polyketide synthase enzymology, namely the definition of a module, has been challenged by Abe and co-workers in their recent study. With this new understanding has emerged renewed hope for engineering these assembly lines to produce new materials and medicines.
March 21, 2017: Angewandte Chemie
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