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Search for "methyltransferase" in Full Text gives 36 result(s) in Beilstein Journal of Organic Chemistry.

Production of non-natural 5-methylorsellinate-derived meroterpenoids in Aspergillus oryzae

  • Jia Tang,
  • Yixiang Zhang and
  • Yudai Matsuda

Beilstein J. Org. Chem. 2024, 20, 638–644, doi:10.3762/bjoc.20.56

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  • cyclases responsible for DMOA-derived compounds. To achieve this goal, we first aimed to establish a production system for the 4-desmethyl analogue of (6R,10′R)-epoxyfarnesyl-DMOA methyl ester by utilizing the polyketide synthase FncE, the prenyltransferase FncB, the O-methyltransferase InsA1, and the FAD
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Published 20 Mar 2024

Chemical and biosynthetic potential of Penicillium shentong XL-F41

  • Ran Zou,
  • Xin Li,
  • Xiaochen Chen,
  • Yue-Wei Guo and
  • Baofu Xu

Beilstein J. Org. Chem. 2024, 20, 597–606, doi:10.3762/bjoc.20.52

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  • activate the BGCs of this strain, we employed a combination of elicitors in our fermentation media, including histone deacetylase inhibitors and DNA methyltransferase inhibitors. We developed two specialized media, XISR I and XISR III, which outperformed the traditional potato dextrose broth (PDB) in
  • cytochrome P450, pyridoxal-dependent decarboxylase, glutamine synthase, and tryptophan dimethyltransferase (Figure 5). These genes are likely crucial for the biosynthesis of the newly isolated alkaloids, 1 and 2. In examining the XL-F41 genome for methyltransferase domain-containing BGCs, we found a
  • methyltransferase near BGC 7.3, suggesting its involvement in adding a methoxy group at the C16 position of compound 1. From these key enzyme genes, we propose a hypothetical biosynthetic pathway (Figure 5). Compounds 1 and 2 are hypothesized to be synthesized from a tryptophan precursor via a shared biosynthetic
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Published 15 Mar 2024

A myo-inositol dehydrogenase involved in aminocyclitol biosynthesis of hygromycin A

  • Michael O. Akintubosun and
  • Melanie A. Higgins

Beilstein J. Org. Chem. 2024, 20, 589–596, doi:10.3762/bjoc.20.51

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  • dehydrogenase Hyg17 to form neo-inosose, followed by a transamination to neo-inosamine-2 by the aminotransferase Hyg8. The methyltransferase Hyg6 would then install a methyl group which would set up cyclization of the methylenedioxy group by Hyg7. This biosynthetic pathway has been proposed based on gene
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Published 14 Mar 2024

Recent developments in the engineered biosynthesis of fungal meroterpenoids

  • Zhiyang Quan and
  • Takayoshi Awakawa

Beilstein J. Org. Chem. 2024, 20, 578–588, doi:10.3762/bjoc.20.50

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  • metabolic genes for ease of gene transfer and high substance production capabilities [10][11]. The expression of trt4 (polyketide synthase, PKS), trt2 (prenyltransferase, PT), trt5 (methyltransferase, MT), trt8 (flavin-dependent monooxygenase, FMO), and trt1 (meroterpenoid cyclase, CYC) in A. oryzae NSAR1
  • ) were expressed in A. oryzae to produce the intermediate 15. Next, genes encoding a short-chain oxidoreductase (SDR), methyltransferase (MT), cytochrome P450 oxygenase (P450), and FMO from various fungi were additionally expressed in A. oryzae expessing subABCDE to produce 22 bioactive meroterpenoids
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Published 13 Mar 2024

Discovery of unguisin J, a new cyclic peptide from Aspergillus heteromorphus CBS 117.55, and phylogeny-based bioinformatic analysis of UngA NRPS domains

  • Sharmila Neupane,
  • Marcelo Rodrigues de Amorim and
  • Elizabeth Skellam

Beilstein J. Org. Chem. 2024, 20, 321–330, doi:10.3762/bjoc.20.32

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  • bond formation. Additional common domains include epimerization (E) domains for converting naturally occurring ʟ-amino acids to ᴅ-amino acids, methyltransferase (MT) domains that typically methylate specific N atoms, and terminal condensation (CT) domains which cyclize the growing peptide chain and
  • analyzed by LC–MS for comparison of the retention times. Structures of unguisins. Chemical structures of unguisin J (1) and unguisin B (2). Key gHMBC and gCOSY correlations, and NOESY interactions of 1. Clinker analysis of identified unguisin-encoding BGCs. UngE’ is a methyltransferase that methylates
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Published 19 Feb 2024

Functions of enzyme domains in 2-methylisoborneol biosynthesis and enzymatic synthesis of non-natural analogs

  • Binbin Gu,
  • Lin-Fu Liang and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 1452–1459, doi:10.3762/bjoc.19.104

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  • by two sequential cyclisation reactions to A and B, and terminal quenching with water. This hypothesis was confirmed by the discovery of the biosynthetic genes coding for a GPP methyltransferase (GPPMT) and a type I terpene synthase termed 2-methylisoborneol synthase (2MIBS) [23][24]. Interestingly
  • , the pathway to 1 can be reconstituted in vitro using the methyltransferase humMT from Micromonospora humi for the methylation of dimethylallyl diphosphate (DMAPP) to 2-methylisopentenyl diphosphate (2-Me-IPP) [25], followed by coupling with DMAPP to 2-Me-GPP and terpene cyclisation using farnesyl
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Published 22 Sep 2023

Intermediates and shunt products of massiliachelin biosynthesis in Massilia sp. NR 4-1

  • Till Steinmetz,
  • Blaise Kimbadi Lombe and
  • Markus Nett

Beilstein J. Org. Chem. 2023, 19, 909–917, doi:10.3762/bjoc.19.69

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  • protein RS02200: FAAL: fatty acyl-AMP ligase; ACP: acyl carrier protein; KS: β-ketoacyl synthase; AT: acyltransferase; KR: ketoreductase; C: condensation; A: adenylation; MT: methyltransferase; PCP: peptidyl carrier protein. A discrete enzyme, the thiazolinyl imide reductase RS02195 (Red), catalyzes the
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Published 23 Jun 2023

A Streptomyces P450 enzyme dimerizes isoflavones from plants

  • Run-Zhou Liu,
  • Shanchong Chen and
  • Lihan Zhang

Beilstein J. Org. Chem. 2022, 18, 1107–1115, doi:10.3762/bjoc.18.113

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  • coclaurine [28]. The absence of the product 1 in vitro is reasonable because the biosynthesis of 1 requires an additional methyltransferase from S. cattleya for the methoxy group formation. Substrate scope and reaction mechanism After identification of CYP158C1 as the isoflavone dimerization enzyme, we next
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Published 26 Aug 2022

New azodyrecins identified by a genome mining-directed reactivity-based screening

  • Atina Rizkiya Choirunnisa,
  • Kuga Arima,
  • Yo Abe,
  • Noritaka Kagaya,
  • Kei Kudo,
  • Hikaru Suenaga,
  • Junko Hashimoto,
  • Manabu Fujie,
  • Noriyuki Satoh,
  • Kazuo Shin-ya,
  • Kenichi Matsuda and
  • Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2022, 18, 1017–1025, doi:10.3762/bjoc.18.102

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  • vitro assay elucidated the tailoring step of azodyrecin biosynthesis, which is mediated by the S-adenosylmethionine (SAM)-dependent methyltransferase Ady1. This study paves the way for the targeted isolation of aliphatic azoxy natural products through a genome-mining approach and further investigations
  • of their biosynthetic mechanisms. Keywords: biosynthesis; methyltransferase; natural azoxides; reactivity-based screening; Streptomyces; Introduction Azoxy natural products are a rare yet intriguing class of natural products with various beneficial biological properties, such as antibacterial
  • the biosynthesis of the methyl ester, which is unique to azodyrecins. To this end, we characterized the putative SAM-dependent methyltransferase Ady1 in vitro to assess its activity against the carboxylic acid 11, which was prepared by the hydrolysis of compound 8 under basic conditions. When acid 11
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Published 10 Aug 2022

The stereochemical course of 2-methylisoborneol biosynthesis

  • Binbin Gu,
  • Anwei Hou and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 818–824, doi:10.3762/bjoc.18.82

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  • processing through (R)-2-Me-LPP [23]. The GPP methyltransferase (GPPMT) and the 2-methylisoborneol synthase (2MIBS) and their coding genes were discovered and functionally characterized, giving further evidence for the biosynthetic pathway to compound 1 [23][24][25]. As we have recently demonstrated, the
  • biosynthesis of 1 can also be reconstituted in vitro through coupling of dimethylallyl diphosphate (DMAPP) with 2-methyl-IPP (2-Me-IPP; IPP = isopentenyl diphosphate) to 2-Me-GPP using farnesyl diphosphate synthase (FPPS), followed by cyclization through 2MIBS to 1 [26]. A recently described methyltransferase
  • from Micromonospora humi can convert DMAPP into (R)-2-Me-IPP with a methyltransferase [27], naturally providing the C6 building block for this hypothetical alternative pathway towards 1 (Scheme 1B). Today the genomes of many bacteria from the genus Streptomyces have been made available, showing that
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Published 08 Jul 2022

Synthesis of O6-alkylated preQ1 derivatives

  • Laurin Flemmich,
  • Sarah Moreno and
  • Ronald Micura

Beilstein J. Org. Chem. 2021, 17, 2295–2301, doi:10.3762/bjoc.17.147

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  • methylation reaction is likely to be catalyzed by the product of the gene huiC, which encodes a SAM-dependent methyltransferase [18]. To the best of our knowledge, in contrast to m6preQ0 [17] the reduced counterpart 7-aminomethyl-O6-methyl-7-deazaguanine m6preQ1 has not yet been reported to be isolated from
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Published 02 Sep 2021

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

  • Nikita Brodyagin,
  • Martins Katkevics,
  • Venubabu Kotikam,
  • Christopher A. Ryan and
  • Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

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Published 19 Jul 2021

4-Hydroxy-3-methyl-2(1H)-quinolone, originally discovered from a Brassicaceae plant, produced by a soil bacterium of the genus Burkholderia sp.: determination of a preferred tautomer and antioxidant activity

  • Dandan Li,
  • Naoya Oku,
  • Yukiko Shinozaki,
  • Yoichi Kurokawa and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1489–1494, doi:10.3762/bjoc.16.124

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  • methyltransferase [27]. Entry of malonate as the acylate precursor into this pathway is proposed to yield 3 (4 in the original literature) [29]. Thus, 1 is very likely to be biosynthesized by the same mechanism followed by additional methylation on C3. Compound 1 is reportedly inhibitory to Mycobacterium
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Published 26 Jun 2020

Chemical synthesis of tripeptide thioesters for the biotechnological incorporation into the myxobacterial secondary metabolite argyrin via mutasynthesis

  • David C. B. Siebert,
  • Roman Sommer,
  • Domen Pogorevc,
  • Michael Hoffmann,
  • Silke C. Wenzel,
  • Rolf Müller and
  • Alexander Titz

Beilstein J. Org. Chem. 2019, 15, 2922–2929, doi:10.3762/bjoc.15.286

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  • antipseudomonal activity. The biosynthetic pathway for argyrin production in Cystobacter sp. SBCb004 (Arg1, radical SAM-dependent methyltransferase; Arg2/Arg3, nonribosomal peptide synthetases; Arg4, O‑methyltransferase; Arg5, tryptophan 2,3-dioxygenase). The initial tripeptide of the biosynthesis of the argyrins
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Published 05 Dec 2019

Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering

  • Eric J. N. Helfrich,
  • Geng-Min Lin,
  • Christopher A. Voigt and
  • Jon Clardy

Beilstein J. Org. Chem. 2019, 15, 2889–2906, doi:10.3762/bjoc.15.283

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  • sodorifen [58] biosynthesis for example, require the action of a methyltransferase preceding cyclization. Surprisingly, more and more terpene BGCs are characterized that do not harbor classical TCs, but instead use a variety of different enzyme classes for the cyclization reaction. These atypical terpene
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Published 29 Nov 2019

Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.

  • Amit Raj Sharma,
  • Enjuro Harunari,
  • Tao Zhou,
  • Agus Trianto and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2327–2332, doi:10.3762/bjoc.15.225

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  • methyltransferase, followed by 1,2-hydride shift and deprotonation, and a subsequent reduction of the exo-methylene intermediate gives rise to a methyl group (Scheme 2) [18]. The presence of the exo-methylene intermediate was experimentally proved but the enzyme responsible for the double bond reduction has not
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Published 30 Sep 2019

A review of the total syntheses of triptolide

  • Xiang Zhang,
  • Zaozao Xiao and
  • Hongtao Xu

Beilstein J. Org. Chem. 2019, 15, 1984–1995, doi:10.3762/bjoc.15.194

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  • pathways involved in the regulation of reactive oxygen species (ROS) and/or nitric oxide (NO) [9], histone methyltransferase [10], HSP70 [11], Jak2, Bcl-2/Bax [12], caspase 8 [13], NF-κB [14], X-linked inhibitor of apoptosis protein (XIAP) [15], MAPK, PI3K [16], and MPK1, ERK-1/2, and JNK-1/2 [17]. The
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Published 22 Aug 2019

Genomics-inspired discovery of massiliachelin, an agrochelin epimer from Massilia sp. NR 4-1

  • Jan Diettrich,
  • Hirokazu Kage and
  • Markus Nett

Beilstein J. Org. Chem. 2019, 15, 1298–1303, doi:10.3762/bjoc.15.128

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  • bioinformatics as well as spectroscopy. First, we analyzed whether the isolated natural product possesses a D- or L-configured thiazoline ring. Previous studies had revealed that the D-thiazoline ring in pyochelin is due to an unusual methyltransferase-like epimerization domain in the biosynthesis protein PchE
  • , fatty acyl-AMP ligase; ACP, acyl carrier protein; KS, β-ketoacyl synthase; AT, acyltransferase; KR, ketoreductase; C, condensation; A, adenylation; MT, methyltransferase; PCP, peptidyl carrier protein; TE, thioesterase. The asterisk indicates a methyltransferase-like epimerization domain. C) UV
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Published 13 Jun 2019

Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction

  • Maryna V. Murlykina,
  • Oleksandr V. Kolomiets,
  • Maryna M. Kornet,
  • Yana I. Sakhno,
  • Sergey M. Desenko,
  • Victoriya V. Dyakonenko,
  • Svetlana V. Shishkina,
  • Oleksandr A. Brazhko,
  • Vladimir I. Musatov,
  • Alexander V. Tsygankov,
  • Erik V. Van der Eycken and
  • Valentyn A. Chebanov

Beilstein J. Org. Chem. 2019, 15, 1281–1288, doi:10.3762/bjoc.15.126

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  • ]pyridine-4-carboxamides being SMYD2 inhibitors (an oncogenic methyltransferase that represses the functional activity of the tumor suppressor proteins p53 and RB); the similar structures can be obtained using the methodology of sequential Doebner- and Ugi-type MCRs. In the present work we combined several
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Published 12 Jun 2019

Phylogenomic analyses and distribution of terpene synthases among Streptomyces

  • Lara Martín-Sánchez,
  • Kumar Saurabh Singh,
  • Mariana Avalos,
  • Gilles P. van Wezel,
  • Jeroen S. Dickschat and
  • Paolina Garbeva

Beilstein J. Org. Chem. 2019, 15, 1181–1193, doi:10.3762/bjoc.15.115

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  • -MIB (2). First, GPP is methylated to 14 by a SAM-dependent methyltransferase, followed by a terpene synthase catalysed cyclisation through a cationic cascade to 2. Oxidation products derived from 3 by the cytochrome P450 monooxygenase that is genetically clustered with the epi-isozizaene synthase in
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Published 29 May 2019

Learning from B12 enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

  • Keishiro Tahara,
  • Ling Pan,
  • Toshikazu Ono and
  • Yoshio Hisaeda

Beilstein J. Org. Chem. 2018, 14, 2553–2567, doi:10.3762/bjoc.14.232

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  • ) that is an intermediate in the synthesis of AB also has lower toxicity than inorganic arsenics. Moreover, inorganic arsenics could be converted to methylated arsenics via human or animal metabolism involving a methyltransferase and a reductase [80][81][82]. Thus, biomimetic transformation from
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Published 02 Oct 2018

An overview of recent advances in duplex DNA recognition by small molecules

  • Sayantan Bhaduri,
  • Nihar Ranjan and
  • Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

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  • topoisomerase I and prokaryotic DNA methyltransferase (MTase) at micromolar concentrations. Rangappa et al. recently reported the synthesis of a series of novel bisbenzimidazole derivatives and evaluated their antiproliferative and antiangiogenic activity properties. Conjugates 50 and 51 were found to be not
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Published 16 May 2018

Volatiles from three genome sequenced fungi from the genus Aspergillus

  • Jeroen S. Dickschat,
  • Ersin Celik and
  • Nelson L. Brock

Beilstein J. Org. Chem. 2018, 14, 900–910, doi:10.3762/bjoc.14.77

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  • an even number of carbons are much more widespread. Furthermore, esterification with S-adenosyl-l-methionine (SAM) by a methyltransferase is a very common process in nature, while ethyl esters are rarer and likely require a two-step pathway through reduction of acetyl-CoA to ethanol and its
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Published 24 Apr 2018

Synthetic mRNA capping

  • Fabian Muttach,
  • Nils Muthmann and
  • Andrea Rentmeister

Beilstein J. Org. Chem. 2017, 13, 2819–2832, doi:10.3762/bjoc.13.274

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  • ; enzymatic capping; methyltransferase; RNA; Introduction The 5′-cap is a hallmark of eukaryotic mRNA and involved in numerous interactions required for cellular functions. Chemically, the 5′-cap consists of an inverted 7-methylguanosine connected to the rest of the eukaryotic mRNA via a 5′–5′ triphosphate
  • responsible guanylyltransferase uses GTP as substrate and forms a covalent enzyme-(lysyl-N)-GMP intermediate, reminiscent of DNA ligase-AMP intermediates [30][31]. Finally, the cap structure is methylated at the N7-position by an RNA(guanine-N7)methyltransferase using S-adenoysl-L-methionine (AdoMet) as a
  • -terminal half and the methyltransferase in the C-terminal half of the large D1 protein, whereas the small D12 protein has no catalytic activity but activates D1 [36][37][38]. Originally, the RNA capping with the Vaccinia capping apparatus was reported to be inefficient [35][37][39][40]. To date, the enzyme
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Published 20 Dec 2017

N-Propargylamines: versatile building blocks in the construction of thiazole cores

  • S. Arshadi,
  • E. Vessally,
  • L. Edjlali,
  • R. Hosseinzadeh-Khanmiri and
  • E. Ghorbani-Kalhor

Beilstein J. Org. Chem. 2017, 13, 625–638, doi:10.3762/bjoc.13.61

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  • pharmacological activities. For example, abafungin (Figure 1) is an antifungal drug marketed worldwide for the treatment of dermatomycoses. It works by inhibiting the enzyme sterol 24-C-methyltransferase [1][2][3][4]. Febuxostat, also known by its brand name adenuric is a xanthine oxidase inhibitor that helps to
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Published 30 Mar 2017
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