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polyketide synthase

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https://www.readbyqxmd.com/read/28334262/discriminating-the-reaction-types-of-plant-type-iii-polyketide-synthases
#1
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
#2
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
#3
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...
March 22, 2017: Organic Letters
https://www.readbyqxmd.com/read/28326145/polyketide-stereocontrol-a-study-in-chemical-biology
#4
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
#5
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 17, 2017: Biochimie
https://www.readbyqxmd.com/read/28322495/polyketide-synthase-modules-redefined
#6
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
https://www.readbyqxmd.com/read/28299197/new-insights-into-bacterial-type-ii-polyketide-biosynthesis
#7
REVIEW
Zhuan Zhang, Hai-Xue Pan, Gong-Li Tang
Bacterial aromatic polyketides, exemplified by anthracyclines, angucyclines, tetracyclines, and pentangular polyphenols, are a large family of natural products with diverse structures and biological activities and are usually biosynthesized by type II polyketide synthases (PKSs). Since the starting point of biosynthesis and combinatorial biosynthesis in 1984-1985, there has been a continuous effort to investigate the biosynthetic logic of aromatic polyketides owing to the urgent need of developing promising therapeutic candidates from these compounds...
2017: F1000Research
https://www.readbyqxmd.com/read/28295904/a-fungal-n-dimethylallyltryptophan-metabolite-from-fusarium-fujikuroi
#8
Birgit Arndt, Slavica Janevska, Robin Schmid, Florian Hübner, Bettina Tudzynski, Hans-Ulrich Humpf
The range of secondary metabolites (SMs) produced by the rice pathogen Fusarium fujikuroi is quite broad. Several polyketides, nonribosomal peptides and terpenes have been identified. However, no products of dimethylallyltryptophan synthases (DMATSs) have been elucidated so far, though two putative DMATS genes are present in the F. fujikuroi genome. In this study, the product derived from one of the two DMATSs, DMATS1 (FFUJ_09179), has been identified in vivo with the help of the software MZmine 2. Detailed structure elucidation showed that this metabolite is a reversely N-prenylated tryptophan, depicting a rather rare form of prenylation...
March 10, 2017: Chembiochem: a European Journal of Chemical Biology
https://www.readbyqxmd.com/read/28293034/characterization-of-bafilomycin-biosynthesis-in-kitasatospora-setae-km-6054-and-comparative-analysis-of-gene-clusters-in-actinomycetales-microorganisms
#9
Ayako Nara, Takuya Hashimoto, Mamoru Komatsu, Makoto Nishiyama, Tomohisa Kuzuyama, Haruo Ikeda
Bafilomycins A1, C1 and B1 (setamycin) produced by Kitasatospora setae KM-6054 belong to the plecomacrolide family, which exhibit antibacterial, antifungal, antineoplastic and immunosuppressive activities. An analysis of gene clusters from K. setae KM-6054 governing the biosynthesis of bafilomycins revealed that it contains five large open reading frames (ORFs) encoding the multifunctional polypeptides of bafilomycin polyketide synthases (PKSs). These clustered PKS genes, which are responsible for bafilomycin biosynthesis, together encode 11 homologous sets of enzyme activities, each catalyzing a specific round of polyketide chain elongation...
March 15, 2017: Journal of Antibiotics
https://www.readbyqxmd.com/read/28292933/complete-elucidation-of-the-late-steps-of-bafilomycin-biosynthesis-in-streptomyces-lohii
#10
Zhong Li, Lei Du, Wei Zhang, Xingwang Zhang, Yuanyuan Jiang, Kun Liu, Ping Men, Huifang Xu, Jeffrey L Fortman, David H Sherman, Bing Yu, Song Gao, Shengying Li
Bafilomycins are an important subgroup of polyketides with diverse biological activities and possible applications as specific inhibitors of vacuolar H+-ATPase. However, the general toxicity and structural complexity of bafilomycins present formidable challenges to drug design via chemical modification, prompting interests in improving bafilomycin activities via biosynthetic approaches. Two bafilomycin biosynthetic gene clusters have been identified, but their post- polyketide synthase (PKS) tailoring steps for structural diversification and bioactivity improvement remain largely unknown...
March 14, 2017: Journal of Biological Chemistry
https://www.readbyqxmd.com/read/28272514/transcriptomic-insight-into-terpenoid-and-carbazole-alkaloid-biosynthesis-and-functional-characterization-of-two-terpene-synthases-in-curry-tree-murraya-koenigii
#11
Seema Meena, Sarma Rajeev Kumar, Varun Dwivedi, Anup Kumar Singh, Chandan S Chanotiya, Md Qussen Akhtar, Krishna Kumar, Ajit Kumar Shasany, Dinesh A Nagegowda
Curry tree (Murraya koenigii L.) is a rich source of aromatic terpenes and pharmacologically important carbazole alkaloids. Here, M. koenigii leaf transcriptome was generated to gain insight into terpenoid and alkaloid biosynthesis. Analysis of de novo assembled contigs yielded genes for terpene backbone biosynthesis and terpene synthases. Also, gene families possibly involved in carbazole alkaloid formation were identified that included polyketide synthases, prenyltransferases, methyltransferases and cytochrome P450s...
March 8, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28271875/in-vivo-selected-pyrazinoic-acid-resistant-m-tuberculosis-strains-harbor-missense-mutations-in-the-aspartate-decarboxylase-pand-and-the-unfoldase-clpc1
#12
Pooja Gopal, Rokeya Tasneen, Michelle Yee, Jean-Philippe Lanoix, Jansy Passiflora Sarathy, George Rasic, Liping Li, Veronique Dartois, E Nuermberger, Thomas Dick
Through mutant selection on agar containing pyrazinoic acid (POA), the bioactive form of the prodrug pyrazinamide (PZA), we recently showed that missense mutations in the aspartate decarboxylase PanD and the unfoldase ClpC1, and loss-of-function mutation of polyketide synthases Mas and PpsA-E involved in phthiocerol dimycocerosate synthesis, cause resistance to POA and PZA in Mycobacterium tuberculosis. Here we first asked whether these in vitro-selected POA/PZA-resistant mutants are attenuated in vivo, to potentially explain the lack of evidence of these mutations among PZA-resistant clinical isolates...
March 8, 2017: ACS Infectious Diseases
https://www.readbyqxmd.com/read/28264562/heterologous-biosynthesis-of-spinosad-an-omics-guided-large-polyketide-synthase-gene-cluster-reconstitution-in-streptomyces
#13
Gao-Yi Tan, Kunhua Deng, Xinhua Liu, Hui Tao, Yingying Chang, Jia Chen, Kai Chen, Zhi Sheng, Zixin Deng, Tiangang Liu
With the advent of the genomics era, heterologous gene expression has been used extensively as a means of accessing natural products (NPs) from environmental DNA samples. However, the heterologous production of NPs often has very low efficiency or is unable to produce targeted NPs. Moreover, due to the complicated transcriptional and metabolic regulation of NP biosynthesis in native producers, especially in the cases of genome mining, it is also difficult to rationally and systematically engineer synthetic pathways to improved NPs biosynthetic efficiency...
March 13, 2017: ACS Synthetic Biology
https://www.readbyqxmd.com/read/28255687/identification-of-the-orsellinic-acid-synthase-pks63787-for-the-biosynthesis-of-antroquinonols-in-antrodia-cinnamomea
#14
Po-Wei Yu, Ting-Yu Cho, Ruey-Fen Liou, Shean-Shong Tzean, Tzong-Huei Lee
Antrodia cinnamomea, an endemic basidiomycete used as a health food in Taiwan, is known to synthesize antroquinonols, which were reported to have notable medicinal potential in oncology and immunology. However, the biosynthetic pathway of these compounds is currently unclear. Our previous study showed that a pks63787 knockout mutant of A. cinnamomea (∆pks63787) is deficient in the biosynthesis of several aromatic metabolites. In this study, we pointed by phylogenetic analysis that pks63787 likely encodes an orsellinic acid synthase...
March 2, 2017: Applied Microbiology and Biotechnology
https://www.readbyqxmd.com/read/28252962/merocyclophanes-c-and-d-from-the-cultured-freshwater-cyanobacterium-nostoc-sp-uic-10110
#15
Daniel S May, Wei-Lun Chen, Daniel D Lantvit, Xiaoli Zhang, Aleksej Krunic, Joanna E Burdette, Alessandra Eustaquio, Jimmy Orjala
Merocyclophanes C and D (1 and 2) were isolated from the cell extract of the cultured cyanobacterium UIC 10110. The structures were determined by one-dimensional nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectrometry and confirmed by 2D NMR techniques. The absolute configurations were determined using electronic circular dichroism spectroscopy. Merocyclophanes C and D represent the first known analogues of the merocyclophane core structure, a recently discovered scaffold of [7,7] paracyclophanes characterized by an α-branched methyl at C-1/C-14; 1 and 2 showed antiproliferative activity against the MDA-MB-435 cell line with IC50 values of 1...
March 2, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28251756/functional-genomics-guided-discovery-of-a-light-activated-phytotoxin-in-the-wheat-pathogen-parastagonospora-nodorum-via-pathway-activation
#16
Yit-Heng Chooi, Guozhi Zhang, Jinyu Hu, Mariano Jordi Muria-Gonzalez, Phuong Tran, Amber Pettitt, Alex Maier, Russell A Barrow, Peter S Solomon
Parastagonospora nodorum is an important pathogen of wheat. The contribution of secondary metabolites to this pathosystem is poorly understood. A biosynthetic gene cluster (SNOG_08608-08616) has been shown to be upregulated during the late stage of P. nodorum wheat leaf infection. The gene cluster shares several homologues with the Cercospora nicotianae CTB gene cluster encoding the biosynthesis of cercosporin. Activation of the gene cluster by overexpression (OE) of the transcription factor gene (SNOG_08609) in P...
March 2, 2017: Environmental Microbiology
https://www.readbyqxmd.com/read/28240912/domain-targeted-metabolomics-delineates-the-heterocycle-assembly-steps-of-colibactin-biosynthesis
#17
Eric P Trautman, Alan R Healy, Emilee E Shine, Seth B Herzon, Jason M Crawford
Modular polyketide synthases (PKSs) and nonribosomal peptide synthetases (NRPSs) comprise giant multidomain enzymes responsible for the "assembly line" biosynthesis of many genetically encoded small molecules. Site-directed mutagenesis, protein biochemical, and structural studies have focused on elucidating the catalytic mechanisms of individual multidomain proteins and protein domains within these megasynthases. However, probing their functions at the cellular level typically has invoked the complete deletion (or overexpression) of multidomain-encoding genes or combinations of genes and comparing those mutants with a control pathway...
March 10, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28238725/functional-and-structural-analysis-of-programmed-c-methylation-in-the-biosynthesis-of-the-fungal-polyketide-citrinin
#18
Philip A Storm, Dominik A Herbst, Timm Maier, Craig A Townsend
Fungal polyketide synthases (PKSs) are large, multidomain enzymes that biosynthesize a wide range of natural products. A hallmark of these megasynthases is the iterative use of catalytic domains to extend and modify a series of enzyme-bound intermediates. A subset of these iterative PKSs (iPKSs) contains a C-methyltransferase (CMeT) domain that adds one or more S-adenosylmethionine (SAM)-derived methyl groups to the carbon framework. Neither the basis by which only specific positions on the growing intermediate are methylated ("programming") nor the mechanism of methylation are well understood...
March 16, 2017: Cell Chemical Biology
https://www.readbyqxmd.com/read/28229977/non-ribosomal-peptide-synthetases-identifying-the-cryptic-gene-clusters-and-decoding-the-natural-product
#19
REVIEW
Mangal Singh, Sandeep Chaudhary, Dipti Sareen
Non-ribosomal peptide synthetases (NRPSs) and polyketide synthases (PKSs) present in bacteria and fungi are the major multi-modular enzyme complexes which synthesize secondary metabolites like the pharmacologically important antibiotics and siderophores. Each of the multiple modules of an NRPS activates a different amino or aryl acid, followed by their condensation to synthesize a linear or cyclic natural product. The studies on NRPS domains, the knowledge of their gene cluster architecture and tailoring enzymes have helped in the in silico genetic screening of the ever-expanding sequenced microbial genomic data for the identification of novel NRPS/PKS clusters and thus deciphering novel non-ribosomal peptides (NRPs)...
March 2017: Journal of Biosciences
https://www.readbyqxmd.com/read/28222482/functional-reconstitution-of-the-mycobacterium-tuberculosis-long-chain-acyl-coa-carboxylase-from-multiple-acyl-coa-subunits
#20
Bernardo Bazet Lyonnet, Lautaro Diacovich, Gabriela Gago, Lucie Spina, Fabienne Bardou, Anne Lemassu, Annaïk Quémard, Hugo Gramajo
Mycobacterium tuberculosis produces a large number of structurally diverse lipids that have been implicated in the pathogenicity, persistence and antibiotic resistance of this organism. Most building blocks involved in the biosynthesis of all these lipids are generated by acyl-CoA carboxylases (ACCase) whose subunit composition and physiological roles have not yet been clearly established. A rather controversial data in the literature refers to the exact protein composition and substrate specificity of the enzyme complex that produces the long-chain α-carboxy-acyl-CoAs; one of the substrates involved in the last step of condensation mediated by the polyketide synthase Pks13 to synthesize mature mycolic acids...
February 21, 2017: FEBS Journal
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