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Search for "polyketides" in Full Text gives 62 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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  • pathway; their non-terpenoid portions can be polyketides, indole, or shikimate-derived compounds [1][2][3]. Their hybrid nature significantly contributes to their structural diversity and wide range of biological activities. Although meroterpenoids are found ubiquitously in nature, as both primary and
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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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  • polyketides, alkaloids, sterol derivatives, terpenoids, and macrolides, with polyketides and alkaloids comprising 40% and 32% of the total, respectively. Alkaloids are a diverse group of compounds with multiple pharmacological activities, including anti-inflammatory, antibacterial, antiviral, insecticidal
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Published 15 Mar 2024

Pseudallenes A and B, new sulfur-containing ovalicin sesquiterpenoid derivatives with antimicrobial activity from the deep-sea cold seep sediment-derived fungus Pseudallescheria boydii CS-793

  • Zhen Ying,
  • Xiao-Ming Li,
  • Sui-Qun Yang,
  • Hong-Lei Li,
  • Xin Li,
  • Bin-Gui Wang and
  • Ling-Hong Meng

Beilstein J. Org. Chem. 2024, 20, 470–478, doi:10.3762/bjoc.20.42

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  • our attention. Several meroterpenoids, alkaloids, polyketides, and sesquiterpenoids from the species displayed various biological properties including anti-inflammatory, antimicrobial, and cytotoxic activities [7][8][9]. In the present work, two rare new examples of sulfur-containing ovalicin
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Published 28 Feb 2024

Identification of the p-coumaric acid biosynthetic gene cluster in Kutzneria albida: insights into the diazotization-dependent deamination pathway

  • Seiji Kawai,
  • Akito Yamada,
  • Yohei Katsuyama and
  • Yasuo Ohnishi

Beilstein J. Org. Chem. 2024, 20, 1–11, doi:10.3762/bjoc.20.1

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  • -dependent deamination pathway for the production of avenalumic acid or p-coumaric acid. Keywords: actinomycetes; avenalumic acid; biosynthesis; p-coumaric acid; polyketides; Introduction The genomes of microorganisms possess diverse biosynthetic gene clusters (BGCs) to produce natural products [1]. In
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Published 02 Jan 2024

Secondary metabolites of Diaporthe cameroonensis, isolated from the Cameroonian medicinal plant Trema guineensis

  • Bel Youssouf G. Mountessou,
  • Élodie Gisèle M. Anoumedem,
  • Blondelle M. Kemkuignou,
  • Yasmina Marin-Felix,
  • Frank Surup,
  • Marc Stadler and
  • Simeon F. Kouam

Beilstein J. Org. Chem. 2023, 19, 1555–1561, doi:10.3762/bjoc.19.112

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  • great structural variability such as polyketides, terpenoids, polyketide synthase–nonribosomal peptide synthetase (PKS–NRPS) alkaloids, and cytochalasins, which have been considered as taxonomic markers of the genus [7][8][9][10]. However, it is worthwhile to mention that the name Phomopsis should no
  • based the comparison of their spectral data with the previously published ones. Discussion The present study describes the isolation of two previously undescribed polyketides, named 5,7-dimethylpseudopithonone (1) and 3,9-diacetylalternariol (2) along with cytochalasins and cytosporones from Diaporthe
  • medicinal plant, Trema guineensis led to the isolation of seventeen secondary metabolites, including two previously undescribed polyketides, namely 5,7-dimethylpseudopithonone (1) and 3,9-diacetylalternariol (2). This study has contributed further to our knowledge of the metabolic diversity within Diaporthe
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Published 13 Oct 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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  • plate. We further identified a cytochrome P450 monooxygenase, CYP158C1, which is able to catalyze the dimerization of isoflavones. CYP158C1 can also dimerize plant-derived polyketides, such as flavonoids and stilbenes. Our work represents a unique bacterial P450 that can dimerize plant polyphenols
  • explored the substrate scope of the catalyst using a variety of plant-derived polyketides (Scheme 1). The results revealed that the 5-OH substitution on isoflavone (see compound 6) was tolerable for dimerization (Figure S15, Supporting Information File 1), whereas the additional 4’-methoxyl group at the B
  • , Supporting Information File 1). Other plant polyketides, such as anthraquinones 19 and 20 and phenylpropanoids 21–24, failed to be dimerized. The reaction mechanism of P450-mediated phenol dimerization is believed to involve oxidative radical–radical coupling, though other mechanisms, such as radical
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Published 26 Aug 2022

Structural basis for endoperoxide-forming oxygenases

  • Takahiro Mori and
  • Ikuro Abe

Beilstein J. Org. Chem. 2022, 18, 707–721, doi:10.3762/bjoc.18.71

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  • endoperoxide containing alkaloids, terpenoids, and polyketides have been isolated from plants, animals, bacteria, fungi, and other organisms (Figure 1) [6][7]. Because of the high reactivity of the cyclic peroxide O–O bond, these compounds exhibit various biological activities [1][2][3][4][5]. For example
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Published 21 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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  • metabolite with a methyl-branched C9 unsaturated acyl chain [31]. Moreover, salinipyrones, produced by a Salinispora strain, were shown to be biosynthetic byproducts of the rosamicin polyketide synthase [32]. Though not a result from Micromonosporaceae, another example of truncated polyketides is citreodiol
  • , a similarly methyl-branched unsaturated fatty acid ester, which is produced by type I polyketide synthase in a Streptomyces strain by a heterologous expression experiment [33]. These facts suggest that 1–5 could be byproducts from the biosynthesis of larger polyketides, but further investigation is
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Published 16 Dec 2021

Nomimicins B–D, new tetronate-class polyketides from a marine-derived actinomycete of the genus Actinomadura

  • Zhiwei Zhang,
  • Tao Zhou,
  • Taehui Yang,
  • Keisuke Fukaya,
  • Enjuro Harunari,
  • Shun Saito,
  • Katsuhisa Yamada,
  • Chiaki Imada,
  • Daisuke Urabe and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2021, 17, 2194–2202, doi:10.3762/bjoc.17.141

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  • Marine Science and Technology, Tokyo University of Marine Science and Technology, 4-5-7, Konan, Minato-ku, Tokyo 108-8477, Japan DHC Corporation, 2-7-1 Minami-Azabu, Minato-ku, Tokyo 106-8571, Japan 10.3762/bjoc.17.141 Abstract Three new tetronate-class polyketides, nomimicins B, C, and D, along with
  • , an antibacterial oxime derivative from Micromonospora [14]. Along the lines of these previous studies, metabolite analysis of actinomycetes from the DSW of Sagami Bay was further conducted, and three new tetronate-class polyketides, nomimicins B (1), C (2), and D (3) were found from a rare
  • medium, and the whole culture broth was extracted with 1-butanol. The extract was subjected to silica gel and ODS column chromatography, and the final purification was achieved by reversed-phase HPLC to yield two new spirotetronate polyketides, nomimicins B (1) and C (2), along with a known compound
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Published 27 Aug 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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  • ; non-ribosomal peptides; polyketides; secondary metabolism; virulence; Introduction To thrive in their natural habitats all organisms from bacteria and fungi to plants and animals need access to sufficient nutritional sources and have to defend themselves against both, competitors and predators
  • molecules like non-ribosomal peptides (NRP), polyketides (PK), terpenes or indole alkaloids [10][11]. The vast majority of fungal BGCs is found in the genomes of members of the Basidiomycota and Ascomycota including the genus Penicillium in which the first BGC was identified in 1990 [12][13][14
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Published 28 Jul 2021

19F NMR as a tool in chemical biology

  • Diana Gimenez,
  • Aoife Phelan,
  • Cormac D. Murphy and
  • Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

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  • the detection of the new compounds in the complex supernatants of organisms producing non-ribosomal peptides and polyketides. It has been especially useful for monitoring the incorporation
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Published 28 Jan 2021

Total synthesis of decarboxyaltenusin

  • Lucas Warmuth,
  • Aaron Weiß,
  • Marco Reinhardt,
  • Anna Meschkov,
  • Ute Schepers and
  • Joachim Podlech

Beilstein J. Org. Chem. 2021, 17, 224–228, doi:10.3762/bjoc.17.22

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  • -3,5-dimethoxybenzene, where the longest linear sequence consists of five steps. The key reaction was a palladium-catalyzed Suzuki coupling of an aromatic boronate with a brominated resorcin derivative. Keywords: biaryls; boronates; mycotoxins; polyketides; Suzuki coupling; Introduction 5’-Methoxy-6
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Published 22 Jan 2021

Nocarimidazoles C and D, antimicrobial alkanoylimidazoles from a coral-derived actinomycete Kocuria sp.: application of 1JC,H coupling constants for the unequivocal determination of substituted imidazoles and stereochemical diversity of anteisoalkyl chains in microbial metabolites

  • Md. Rokon Ul Karim,
  • Enjuro Harunari,
  • Amit Raj Sharma,
  • Naoya Oku,
  • Kazuaki Akasaka,
  • Daisuke Urabe,
  • Mada Triandala Sibero and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 2719–2727, doi:10.3762/bjoc.16.222

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  • habitat [6][7]. Their secondary metabolite machinery is activated in the sea, as indicated by the isolation of enediyne antitumor antibiotics from marine invertebrates. Namenamicin [8] and the shishijimicins [9], the chalicheamicin-type enediyne polyketides, were isolated from a colonial tunicate. These
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Published 05 Nov 2020

Muyocopronones A and B: azaphilones from the endophytic fungus Muyocopron laterale

  • Ken-ichi Nakashima,
  • Junko Tomida,
  • Tomoe Tsuboi,
  • Yoshiaki Kawamura and
  • Makoto Inoue

Beilstein J. Org. Chem. 2020, 16, 2100–2107, doi:10.3762/bjoc.16.177

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  • fungus; modified Mosher’s method; Muyocopron laterale; polyketides; Introduction Azaphilones, which are a class of fungal polyketides with diverse structures, have received growing attention due to their various biological activities, such as the inhibition of some protein–protein interactions [1][2
  • [20][26], while three azaphilone-related polyketides, namely dothideomycetones A, B, and dothideomycetide A, were isolated from the CR17 fungal strain of the Dothideomycetes class (GeneBank accession number JQ867364) [27]. Furthermore, two sesquiterpenoids produced by Pithomyces chartarum
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Published 28 Aug 2020

Syntheses of spliceostatins and thailanstatins: a review

  • William A. Donaldson

Beilstein J. Org. Chem. 2020, 16, 1991–2006, doi:10.3762/bjoc.16.166

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  • William A. Donaldson Department of Chemistry, Marquette University, P. O. Box 1881, Milwaukee, WI 53201-1881, USA 10.3762/bjoc.16.166 Abstract The spliceostatins/thailanstatins are a family of linear peptides/polyketides that inhibit pre-mRNA splicing, and as such act as potent cytotoxic
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Published 13 Aug 2020

A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus Pseudosporangium

  • Shun Saito,
  • Kota Atsumi,
  • Tao Zhou,
  • Keisuke Fukaya,
  • Daisuke Urabe,
  • Naoya Oku,
  • Md. Rokon Ul Karim,
  • Hisayuki Komaki and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1100–1110, doi:10.3762/bjoc.16.97

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  • and subjected to metabolite analysis, which resulted in the discovery of a novel cyclopeptide, pseudosporamide (1), along with three new oligomycin-class polyketides, pseudosporamicins A–C (2–4). The unusual structure of compound 1, featured by a biaryl-bond bridging across a tripeptide scaffold, N
  • chain of the spiroacetal rings, which showed clear contrast to other oligomycin congeners and related polyketides with ring-truncation or expansion. The new macrolides 2–4 displayed potent antimicrobial activity against the Gram-positive bacterium Kocuria rhizohpila and the plant pathogenic fungus
  • discovery of new natural products. Keywords: DFT-based calculation; oligomycin; peptide; polyketides; Pseudosporangium; rare actinomycetes; Introduction Microbial secondary metabolites have been used as therapeutic drugs [1], veterinary medicines [2], agrochemicals [3], food preservatives/colorings [4][5
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Published 25 May 2020

Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment

  • Jan Geldsetzer and
  • Markus Kalesse

Beilstein J. Org. Chem. 2020, 16, 670–673, doi:10.3762/bjoc.16.64

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  • ′-dimethylethane-1,2-diamine. Keywords: cross coupling; myxobacteria; natural product; ribolactone; Z-enamide; Introduction In the course of our program to provide synthetic access to biologically active natural products we targeted complex polyketides and depsipetides [1][2][3][4][5][6][7][8][9][10]. One
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Published 14 Apr 2020

Two new aromatic polyketides from a sponge-derived Fusarium

  • Mada Triandala Sibero,
  • Tao Zhou,
  • Keisuke Fukaya,
  • Daisuke Urabe,
  • Ocky K. Karna Radjasa,
  • Agus Sabdono,
  • Agus Trianto and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2941–2947, doi:10.3762/bjoc.15.289

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  • program from marine fungi, two new aromatic polyketides karimunones A (1) and B (2) and five known compounds (3–7) were isolated from sponge-associated Fusarium sp. KJMT.FP.4.3 which was collected from an Indonesian sponge Xestospongia sp. The structures of these compounds were determined by the analysis
  • . collected in Karimunjawa National Park, Indonesia. This fungus produces a violet pigment in the mycelium and secretes pink to red pigments into the broth medium. Comprehensive chemospectroscopic analysis of the culture extract using HPLC/UV led to the isolation of two new aromatic polyketides, karimunones A
  • database. HPLC/UV-guided purification of the secondary metabolites from this strain led to the isolation of two new polyketides, karimunones A (1) and B (2), together with five known compounds (3–7, Figure 1). Compound 1 was obtained as a red powder. TOF-HRESIMS analysis gave a deprotonated molecule [M − H
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Published 09 Dec 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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  • -position (C2) of the acetate unit (Figure 3B) [13]. In contrast, methylation at the carbons derived from the carbonyl carbon of the acetate (C1) is quite unusual in fatty acids and polyketides. This unusual methylation pattern is reported for the polyketides of eukaryotic algae dinoflagellates. Some of the
  • intermediate, from which deprotonation occurs at C9 to give an internal olefin (Scheme 1). In the case of 1, methylation at the C3 carbon is inconsistent with the regular methylation pattern that occurs in fatty acids synthesized by the FAS (fatty acid synthase) or polyketides from the PKS (polyketide synthase
  • growth was observed. Structure of (2Z,4E)-3-methyl-2,4-decadienoic acid (1). COSY and key HMBC correlations for 1. Methylation pattern that can occur in fatty acids and polyketides. Incorporation of 13C-labeled precursors into 1. C-Methylation of alkenyl carbon in sphingolipid biosynthesis. Biosynthesis
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Published 30 Sep 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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  • remarkable genetic potential to produce a large variety of secondary metabolites with different functions including antibiotics, antifungals, pigments or immunosuppressants [1][2][3]. These are compounds of diverse chemical nature such as polyketides, peptides, aminoglycosides or terpenoids [4][5
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Published 29 May 2019

Synthesis of the polyketide section of seragamide A and related cyclodepsipeptides via Negishi cross coupling

  • Jan Hendrik Lang and
  • Thomas Lindel

Beilstein J. Org. Chem. 2019, 15, 577–583, doi:10.3762/bjoc.15.53

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  • assembled by solution-phase synthesis and an open-chain analogue of the natural product was obtained. Keywords: jasplakinolide; marine natural products; Negishi coupling; polyketides; stereoselective synthesis; Introduction Our program on the synthesis of biologically active natural products with peptide
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Published 28 Feb 2019

Volatiles from the tropical ascomycete Daldinia clavata (Hypoxylaceae, Xylariales)

  • Tao Wang,
  • Kathrin I. Mohr,
  • Marc Stadler and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2018, 14, 135–147, doi:10.3762/bjoc.14.9

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  • different compound classes including fatty acid derivatives and polyketides, aromatic compounds, terpenes, sulfur and nitrogen compounds, and halogenated compounds is produced by ascomycete fungi [1]. Possibly the most widespread volatile secondary metabolite from fungi is (R)-oct-1-en-3-ol (1, Scheme 1), a
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Published 12 Jan 2018

Herpetopanone, a diterpene from Herpetosiphon aurantiacus discovered by isotope labeling

  • Xinli Pan,
  • Nicole Domin,
  • Sebastian Schieferdecker,
  • Hirokazu Kage,
  • Martin Roth and
  • Markus Nett

Beilstein J. Org. Chem. 2017, 13, 2458–2465, doi:10.3762/bjoc.13.242

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  • predatory bacterium Herpetosiphon aurantiacus 114-95T as a test organism. This strain is capable to produce a variety of polyketides and nonribosomal peptides [13][14][15] and possesses pathways to supply specific building blocks for these natural products [16]. Furthermore, genomic analyses revealed that H
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Published 17 Nov 2017

Sulfation and amidinohydrolysis in the biosynthesis of giant linear polyenes

  • Hui Hong,
  • Markiyan Samborskyy,
  • Katsiaryna Usachova,
  • Katharina Schnatz and
  • Peter F. Leadlay

Beilstein J. Org. Chem. 2017, 13, 2408–2415, doi:10.3762/bjoc.13.238

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  • mediomycin from S. blastmyceticus have been recently reported, encoding a separate extension module for all 27 cycles of chain extension [8]. These systems are attractive targets for knowledge-based engineering to produce novel antifungal compounds. A member of this class of polyketides, tetrafibricin from
  • Streptomyces neyagawaensis (Scheme 1), is a potent inhibitor of the fibrinogen receptor, which suggests an even wider potential utility for such compounds [8][9]. We have previously shown that in the biosynthesis of giant macrocyclic antifungal polyketides (so-called marginolactones) compounds bearing a
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Published 13 Nov 2017

The chemistry and biology of mycolactones

  • Matthias Gehringer and
  • Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

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Published 11 Aug 2017
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