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Search for "prenylation" in Full Text gives 18 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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  • -dimethylorsellinic acid (DMOA) serves as a precursor for a wide array of structurally diverse meroterpenoid species [7][8]. The fully substituted nature of DMOA leads to dearomatizing prenylation during the biosynthesis of DMOA-derived meroterpenoids (Figure 1A), facilitating the rearrangement reactions of the
  • polyketide moiety, contributing to structural diversification [9][10]. By contrast, in the biosynthesis of meroterpenoids derived from orsellinic acid and 5-methylorsellinic acid (5-MOA), the prenylation reaction typically occurs at the non-substituted carbon atom and thus preserves the aromaticity of the
  • polyketide portion [11][12][13][14]. One exception has been found in funiculolide biosynthesis, in which a 5-MOA-derived phthalide undergoes dearomatizing prenylation catalyzed by the UbiA-like prenyltransferase FncB (Figure 1B) [15]. In addition to prenyltransferases, transmembrane terpene cyclases play a
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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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  • pathway (Figure 5). Briefly, the prenyl group is attached to tryptophan through a prenylation reaction catalyzed by ShnA, followed by the decarboxylation of the carboxy group by ShnC. Subsequently, compound 2 is formed by the addition of succinimide to N15 in 1 via a reaction catalyzed by ShnB. The
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Published 15 Mar 2024

Tandem Hock and Friedel–Crafts reactions allowing an expedient synthesis of a cyclolignan-type scaffold

  • Viktoria A. Ikonnikova,
  • Cristina Cheibas,
  • Oscar Gayraud,
  • Alexandra E. Bosnidou,
  • Nicolas Casaretto,
  • Gilles Frison and
  • Bastien Nay

Beilstein J. Org. Chem. 2024, 20, 162–169, doi:10.3762/bjoc.20.15

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  • ]. Results and Discussion To test the feasibility of this reaction sequence, the aromatic substrate 1 readily accessible by the prenylation of commercial diethyl benzylmalonate [21] was first used. The photooxygenation of 1 was performed in CH2Cl2 in the presence of methylene blue (MB) as a photosensitizer
  • extend the scope of this tandem reaction sequence towards analogous skeletons, we explored the effect of various substituents on the aromatic cycles. The successive prenylation and then diversity-oriented benzylation (n = 1 for substrates 11a–n) of diethyl malonate (10) afforded a variety of new
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Published 25 Jan 2024

Photoredox catalysis enabling decarboxylative radical cyclization of γ,γ-dimethylallyltryptophan (DMAT) derivatives: formal synthesis of 6,7-secoagroclavine

  • Alessio Regni,
  • Francesca Bartoccini and
  • Giovanni Piersanti

Beilstein J. Org. Chem. 2023, 19, 918–927, doi:10.3762/bjoc.19.70

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  • ]. Regioselective palladium-catalyzed prenylation of 2 with prenylboronic acid pinacol ester and subsequent hydrolysis with LiOH provided the linear prenylated acid 4 in good yield. Coupling acid 4 with N-hydroxyphthalimide using DCC and a catalytic amount of DMAP afforded the key intermediate 5 in 59% yield. With
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Published 26 Jun 2023

Identification of the new prenyltransferase Ubi-297 from marine bacteria and elucidation of its substrate specificity

  • Jamshid Amiri Moghaddam,
  • Huijuan Guo,
  • Karsten Willing,
  • Thomas Wichard and
  • Christine Beemelmanns

Beilstein J. Org. Chem. 2022, 18, 722–731, doi:10.3762/bjoc.18.72

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  • farnesylation of quinoline derivatives, such as 8-hydroxyquinoline-2-carboxylic acid (8-HQA) and quinaldic acid. The results of this study provide new insights into the abundance and diversity of Ptases in marine Flavobacteria and beyond. Keywords: Flavobacteria; prenylation; Saccharomonospora; UbiA-like
  • prenyltransferase; Introduction Marine bacteria harbor an enormous potential to produce structurally diverse natural products, including prenylated aromatic metabolites [1][2]. Prenylation of metabolites most often confers increased biological activities due to enhanced lipophilicity, solubility, and improved
  • binding abilities to target proteins [3]. The prenylation reaction, most often a C–C-bond-forming step between an aromatic acceptor moiety and a prenyl chain, is catalyzed by dedicated dominantly membrane-bound prenyltransferases (Ptases) [4][5][6][7]. Ptases belonging to the UbiA-superfamily are
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Published 22 Jun 2022

Unsaturated fatty acids and a prenylated tryptophan derivative from a rare actinomycete of the genus Couchioplanes

  • Shun Saito,
  • Kanji Indo,
  • Naoya Oku,
  • Hisayuki Komaki,
  • Masashi Kawasaki and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2021, 17, 2939–2949, doi:10.3762/bjoc.17.203

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  • components by COSY and HMBC correlations established 6-prenylated N-acetyltryptophan (Figure 5). The N-acetylation was evident from HMBC correlations from the amide (NH-11) and acetyl methyl protons (H-13) to the amide carbon (C-12), while prenylation at C-6 was supported by HMBC correlations from H-5 and H
  • necessary for their biosynthesis. Prenylated indoles are widely distributed among bacteria, fungi and plants, and all seven positions are subject of prenylation except for the bridgehead carbons [34]. Compound 6 is the acetylated derivative of 6-(3,3-dimethylallyl)-ʟ-tryptophan from Streptomyces sp. SN-593
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Published 16 Dec 2021

Natural products in the predatory defence of the filamentous fungal pathogen Aspergillus fumigatus

  • Jana M. Boysen,
  • Nauman Saeed and
  • Falk Hillmann

Beilstein J. Org. Chem. 2021, 17, 1814–1827, doi:10.3762/bjoc.17.124

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  • with the prenylation of ʟ-tryptophan to dimethylallyltryptophan (DMAT). During several steps DMAT is converted to chanoclavine-I aldehyde, the last mutual intermediate. Branching into different pathways after this intermediate is mainly due to differences in the function of EasA, the enzyme catalysing
  • prenylation of fumigaclavine A leads to fumigaclavine C (19), the final product of fumigaclavine biosynthesis [159]. Biosynthesis of the intermediate festuclavine as well as fumigaclavines A–C is dependent on LaeA regulation [124]. Its numerous bioactive effects hold the potential for a pharmaceutical use
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Published 28 Jul 2021

Molecular basis for the plasticity of aromatic prenyltransferases in hapalindole biosynthesis

  • Takayoshi Awakawa and
  • Ikuro Abe

Beilstein J. Org. Chem. 2019, 15, 1545–1551, doi:10.3762/bjoc.15.157

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  • divided into two types, depending on where the cation is generated in the isoprenoid diphosphate: the “normal” prenylation in which the C-1 is attacked and the “reverse” prenylation in which the C-3 is attacked (Figure 1). It is important to study prenylation types for the chemoenzymatic synthesis of
  • reaction is suppressed in the presence of Mg2+ (Figure 2A) [20]. AmbP3 exhibits tolerant substrate specificity with hapalindole substrates [18]. AmbP3 accepts (10R)-hapalindole U (HU) and G, and transfers the dimethylallyl group in the reverse prenylation mode to give ambiguine H and A, respectively
  • (Figure 2B). Remarkably, AmbP3 also accepts (10S)-hapalindole A (HA), and transfers the dimethylallyl group onto the C-2 carbon of hapalindole A in normal prenylation mode to yield compound 3 (Figure 2B). X-ray crystal structure analysis of AmbP1 To understand the effect of Mg2+ ions on the AmbP1 reaction
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Published 11 Jul 2019

Posttranslational isoprenylation of tryptophan in bacteria

  • Masahiro Okada,
  • Tomotoshi Sugita and
  • Ikuro Abe

Beilstein J. Org. Chem. 2017, 13, 338–346, doi:10.3762/bjoc.13.37

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  • derived from cyanobacteria, including dimethylallylated cyclic peptides, are called cyanobactins [2][37][38]. Although several cyanobactins exhibit significant biological activities, such as antibacterial and enzyme inhibitory properties, the actual biological role of prenylation in cyanobactins is still
  • ABBA fold and exhibits some similarity to other dimethylallyltransferases for cyanobactins and prenyltransferases for indole alkaloids, but lacks similarity to cysteine isoprenyltransferases and ComQs [2][37][38][39][40][41][42][43][44]. Considering the in vitro prenylation analysis of KgpF together
  • the core peptide sequence for directing KgpF is unlikely to be required. In addition, the prenylation reaction by KgpF does not seem to need a specific amino acid motif within the core cyclic peptide, because there is no similarity between the sequences surrounding the two tryptophan residues (PWL and
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Published 22 Feb 2017

Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides

  • Andrew W. Truman

Beilstein J. Org. Chem. 2016, 12, 1250–1268, doi:10.3762/bjoc.12.120

Graphical Abstract
  • transferase (ComQ), which transfers an isoprenyl group to position 3 of the indole side chain of a conserved tryptophan residue [135]. This directly generates a tricyclic structure, presumably via attack of the main chain amide nitrogen onto the iminium intermediate that is generated following prenylation
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Published 20 Jun 2016

Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp2 C–H and sp3 C–H bonds

  • Nivesh Kumar,
  • Santanu Ghosh,
  • Subhajit Bhunia and
  • Alakesh Bisai

Beilstein J. Org. Chem. 2016, 12, 1153–1169, doi:10.3762/bjoc.12.111

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  • dimethylallyl esters 8j underwent smooth decarboxylative prenylation and reverse-prenylation in the presence of 5 mol % of Pd2(dba)3 and 15 mol % dppp in refluxing toluene (7–8 h, 96% yields) to afford prenylated (27a) and reverse-prenylated (27b) structures in 64% and 32% yield, respectively (Scheme 11) [92
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Published 08 Jun 2016

Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen–Cope rearrangement

  • Qinggang Mei,
  • Chun Wang,
  • Zhigang Zhao,
  • Weicheng Yuan and
  • Guolin Zhang

Beilstein J. Org. Chem. 2015, 11, 1220–1225, doi:10.3762/bjoc.11.135

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  • -prenylation of 3-O-methoxymethyl-4′-O-methyl-5-O-prenyl-7-O-benzylkaempferol (8) via para-Claisen–Cope rearrangement catalyzed by Eu(fod)3 in the presence of NaHCO3, and the glycosylation of icaritin (3) are the key steps. Keywords: Claisen–Cope rearrangement; flavonol; icariin; prenylation; regioselectivity
  • group prepared icaritin from phloroglucin through an Algar–Flynn–Oyamada reaction and europium-promoted prenylation [17]. However, a number of challengable problems such as strict conditions, numerous byproducts and poor yields, were calling for our continuous efforts to overcome these hitches [18]. As
  • rearrangement and the bis-glycosylation are the key features of this linear synthesis. Previously, we succeeded in the selective methylation of 4′-OH in kaempferol. In this work, we focus on developing an efficient procedure for the selective prenylation of flavonols for facile access to icariin (1). Results
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Published 20 Jul 2015

Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration

  • Michele Mari,
  • Simone Lucarini,
  • Francesca Bartoccini,
  • Giovanni Piersanti and
  • Gilberto Spadoni

Beilstein J. Org. Chem. 2014, 10, 1991–1998, doi:10.3762/bjoc.10.207

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  • these compounds is of particular interest as 2-prenyltryptophan derivatives have been obtained or isolated from a diverse array of natural sources [66][67] and, in general, prenylation at the indole ring leads to a significant increase in the antioxidant and/or cytotoxic activity of tryptophan
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Published 26 Aug 2014

Recent applications of the divinylcyclopropane–cycloheptadiene rearrangement in organic synthesis

  • Sebastian Krüger and
  • Tanja Gaich

Beilstein J. Org. Chem. 2014, 10, 163–193, doi:10.3762/bjoc.10.14

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  • . Gaich et al. [38][39] used the DVCPR in a biosynthetic investigation targeting the dimethylallyltryptophan synthase. In order to test the biosynthetic hypothesis of the mode of action of the 4-prenylation of indoles by Arigoni and Wenkert (starting from L-tryptophan and dimethylallyl pyrophosphate
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Published 16 Jan 2014

The myxocoumarins A and B from Stigmatella aurantiaca strain MYX-030

  • Tobias A. M. Gulder,
  • Snežana Neff,
  • Traugott Schüz,
  • Tammo Winkler,
  • René Gees and
  • Bettina Böhlendorf

Beilstein J. Org. Chem. 2013, 9, 2579–2585, doi:10.3762/bjoc.9.293

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  • O-methylation, glycosylation, prenylation, oxygenation and subsequent cyclization or dimerization events [34]. Nitrogen-bearing congeners are rather scarce, with the bacterial aminocoumarins, such as the gyrase inhibitor novobiocin, being the most well-known examples [35]. Despite the larger number
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Published 20 Nov 2013

The chemistry of isoindole natural products

  • Klaus Speck and
  • Thomas Magauer

Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243

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  • for a more labile methoxymethyl ether at the benzophenone stage. The following prenylation and formylation proceeded smoothly under the same conditions to give 191b (Scheme 24). Cleavage of the MOM ethers afforded pestalone (192), which could be converted into 193 in a single step by treatment of 192
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Published 10 Oct 2013

Palladium-catalyzed dual C–H or N–H functionalization of unfunctionalized indole derivatives with alkenes and arenes

  • Gianluigi Broggini,
  • Egle M. Beccalli,
  • Andrea Fasana and
  • Silvia Gazzola

Beilstein J. Org. Chem. 2012, 8, 1730–1746, doi:10.3762/bjoc.8.198

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  • performed for the prenylation of tryptophan and tryptamine derivatives, as well as peptides containing tryptophan. Taking into account some experimental evidence obtained from the use of 2-methyl or 2-deuterium-substituted indoles and from [1,1,1-D3]3-methyl-2-butene, the mechanism shown in Scheme 8 was
  • -rich heterocycles. Regioselective alkenylation of the unprotected indole. Plausible mechanism of the selective indole alkenylation, adapted from [49]. Directing-group control in intermolecular indole alkenylation. Direct C–H alkenylation of N-(2-pyridyl)sulfonylindole. N-Prenylation of indoles with 2
  • -methyl-2-butene. Proposed mechanism of the N-indolyl prenylation. Regioselective arylation of indoles by dual C–H functionalization. Plausible mechanism of the selective indole arylation. Chemoselective cyclization of N-allyl-1H-indole-2-carboxamide derivatives. Intramolecular annulations of
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Published 11 Oct 2012

Mutational analysis of a phenazine biosynthetic gene cluster in Streptomyces anulatus 9663

  • Orwah Saleh,
  • Katrin Flinspach,
  • Lucia Westrich,
  • Andreas Kulik,
  • Bertolt Gust,
  • Hans-Peter Fiedler and
  • Lutz Heide

Beilstein J. Org. Chem. 2012, 8, 501–513, doi:10.3762/bjoc.8.57

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  • group of endophenazine A forming an amide bond to the α-amino group of L-Gln. Gene inactivation experiments in the gene cluster proved that ppzM codes for a phenazine N-methyltransferase. The gene ppzV apparently represents a new type of TetR-family regulator, specifically controlling the prenylation in
  • alternative hypotheses may explain this observation: The regulatory gene orf3 may be involved in the regulation of the prenylation; or the deletion of the entire orf4 sequence may have affected the promoter of the prenyltransferase gene ppzP, which is situated downstream of orf4. In order to distinguish
  • 5,10-dihydro-PCA, but not PCA, is the substrate for prenylation by the prenyltransferase PpzP [11]. This may explain why the deletion of ppzZ1-ppzZ2 resulted in a reduced formation of prenylated phenazines. In the ΔppzK-orf12 mutant, finally, the production of both prenylated and nonprenylated
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Published 04 Apr 2012
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