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  1. Article ; Online: Heterologous production of fungal natural products: Reconstitution of biosynthetic gene clusters in model host Aspergillus oryzae.

    Oikawa, Hideaki

    Proceedings of the Japan Academy. Series B, Physical and biological sciences

    2020  Volume 96, Issue 9, Page(s) 420–430

    Abstract: While exploring phytotoxic metabolites from phytopathogenic fungi in the 1970s, we became interested in biosynthetic enzymes that catalyze Diels-Alder reactions involving biosynthesis of several phytotoxins that we isolated. Target enzymes were ... ...

    Abstract While exploring phytotoxic metabolites from phytopathogenic fungi in the 1970s, we became interested in biosynthetic enzymes that catalyze Diels-Alder reactions involving biosynthesis of several phytotoxins that we isolated. Target enzymes were successfully characterized, and this triggered the identification of various Diels-Alderases in a recent decade. Through our Diels-Alderase project in 1990s, we recognized a highly efficient expression system of various biosynthetic genes with Aspergillus oryzae as a host. With the development of tools such as genomic data and bioinformatics analysis to identify biosynthetic gene clusters for natural products, we developed a highly reliable methodology such as hot spot knock-in to elucidate the biosynthetic pathways of representative fungal metabolites including phytotoxic substances. This methodology allows total biosynthesis of natural products and genome mining using silent biosynthetic gene clusters to obtain novel bioactive metabolites. Further applications of this technology are discussed.
    MeSH term(s) Aspergillus oryzae/genetics ; Aspergillus oryzae/metabolism ; Biological Products/metabolism ; Data Mining ; Gene Expression ; Genomics ; Multigene Family/genetics
    Chemical Substances Biological Products
    Language English
    Publishing date 2020-11-11
    Publishing country Japan
    Document type Journal Article
    ZDB-ID 161781-3
    ISSN 1349-2896 ; 0386-2208
    ISSN (online) 1349-2896
    ISSN 0386-2208
    DOI 10.2183/pjab.96.031
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  2. Article ; Online: Reconstitution of biosynthetic machinery of fungal natural products in heterologous hosts.

    Oikawa, Hideaki

    Bioscience, biotechnology, and biochemistry

    2019  Volume 84, Issue 3, Page(s) 433–444

    Abstract: Ascomycota and basidiomycota fungi are prolific sources of biologically active natural products. Recent genomic data and bioinformatic analysis indicate that fungi possess a large number of biosynthetic gene clusters for bioactive natural products but ... ...

    Abstract Ascomycota and basidiomycota fungi are prolific sources of biologically active natural products. Recent genomic data and bioinformatic analysis indicate that fungi possess a large number of biosynthetic gene clusters for bioactive natural products but more than 90% are silent. Heterologous expression in the filamentous fungi as hosts is one of the powerful tools to expression of the silent gene clusters. This review introduces recent studies on the total biosynthesis of representative family members via common platform intermediates, genome mining of novel di- and sesterterpenoids including detailed cyclization pathway, and development of expression host for basidiomycota genes with efficient genome editing method. In addition, this review will discuss the several strategies, for the generation of structural diversity, which are found through these studies.
    MeSH term(s) Ascomycota/genetics ; Ascomycota/metabolism ; Basidiomycota/genetics ; Basidiomycota/metabolism ; Biological Products/metabolism ; Biosynthetic Pathways/genetics ; Genes, Fungal ; Multigene Family
    Chemical Substances Biological Products
    Language English
    Publishing date 2019-11-18
    Publishing country England
    Document type Journal Article ; Review
    ZDB-ID 1106450-x
    ISSN 1347-6947 ; 0916-8451
    ISSN (online) 1347-6947
    ISSN 0916-8451
    DOI 10.1080/09168451.2019.1690976
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  3. Article ; Online: Biosynthesis of indole diterpenes: a reconstitution approach in a heterologous host.

    Ozaki, Taro / Minami, Atsushi / Oikawa, Hideaki

    Natural product reports

    2023  Volume 40, Issue 1, Page(s) 202–213

    Abstract: Covering: 2013 to 2022In this review, we provide an overview elucidating the biosynthetic pathway and heterologous production of fungal indole diterpenes (IDTs). Based on the studies of six IDT biosynthesis, we extracted nature's strategy: (1) two-stage ... ...

    Abstract Covering: 2013 to 2022In this review, we provide an overview elucidating the biosynthetic pathway and heterologous production of fungal indole diterpenes (IDTs). Based on the studies of six IDT biosynthesis, we extracted nature's strategy: (1) two-stage synthesis for the core scaffold and platform intermediates, and (2) late-stage modifications for installing an additional cyclic system on the indole ring. Herein, we describe reconstitution studies applying this strategy to the synthesis of highly elaborated IDTs. We also discuss its potential for future biosynthetic engineering.
    MeSH term(s) Indoles/metabolism ; Diterpenes/metabolism ; Biosynthetic Pathways
    Chemical Substances Indoles ; Diterpenes
    Language English
    Publishing date 2023-01-25
    Publishing country England
    Document type Journal Article ; Review ; Research Support, Non-U.S. Gov't
    ZDB-ID 2002546-4
    ISSN 1460-4752 ; 0265-0568
    ISSN (online) 1460-4752
    ISSN 0265-0568
    DOI 10.1039/d2np00031h
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  4. Article: Reconstitution of biosynthetic machinery of fungal natural products in heterologous hosts

    Oikawa, Hideaki

    Bioscience, biotechnology, and biochemistry. 2020 Mar. 3, v. 84, no. 3

    2020  

    Abstract: Ascomycota and basidiomycota fungi are prolific sources of biologically active natural products. Recent genomic data and bioinformatic analysis indicate that fungi possess a large number of biosynthetic gene clusters for bioactive natural products but ... ...

    Abstract Ascomycota and basidiomycota fungi are prolific sources of biologically active natural products. Recent genomic data and bioinformatic analysis indicate that fungi possess a large number of biosynthetic gene clusters for bioactive natural products but more than 90% are silent. Heterologous expression in the filamentous fungi as hosts is one of the powerful tools to expression of the silent gene clusters. This review introduces recent studies on the total biosynthesis of representative family members via common platform intermediates, genome mining of novel di- and sesterterpenoids including detailed cyclization pathway, and development of expression host for basidiomycota genes with efficient genome editing method. In addition, this review will discuss the several strategies, for the generation of structural diversity, which are found through these studies.
    Keywords Ascomycota ; bioinformatics ; biosynthesis ; biotechnology ; cyclization reactions ; fungi ; heterologous gene expression
    Language English
    Dates of publication 2020-0303
    Size p. 433-444.
    Publishing place Taylor & Francis
    Document type Article
    Note NAL-light
    ZDB-ID 1106450-x
    ISSN 1347-6947 ; 0916-8451
    ISSN (online) 1347-6947
    ISSN 0916-8451
    DOI 10.1080/09168451.2019.1690976
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  5. Article ; Online: Nature's Strategy for Catalyzing Diels-Alder Reaction.

    Oikawa, Hideaki

    Cell chemical biology

    2016  Volume 23, Issue 4, Page(s) 429–430

    Abstract: The enzymes catalyzing a Diels-Alder-type reaction have been attractive targets for organic chemists for years. Recently, Zheng et al. (2016) reported the structure of a formal monofunctional Diels-Alderase PyrI4 complexed with the product and unveiled a ...

    Abstract The enzymes catalyzing a Diels-Alder-type reaction have been attractive targets for organic chemists for years. Recently, Zheng et al. (2016) reported the structure of a formal monofunctional Diels-Alderase PyrI4 complexed with the product and unveiled a detailed catalytic mechanism of a highly important enzyme.
    MeSH term(s) Biocatalysis ; Cycloaddition Reaction ; Intramolecular Oxidoreductases/metabolism ; Lovastatin/metabolism ; Molecular Conformation ; Polyketide Synthases/metabolism
    Chemical Substances Polyketide Synthases (79956-01-7) ; Lovastatin (9LHU78OQFD) ; Intramolecular Oxidoreductases (EC 5.3.-) ; solanapyrone synthase (EC 5.3.99.-)
    Language English
    Publishing date 2016--21
    Publishing country United States
    Document type Journal Article ; Comment
    ISSN 2451-9448
    ISSN (online) 2451-9448
    DOI 10.1016/j.chembiol.2016.04.002
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article ; Online: Biosynthetic machineries of anthraquinones and bisanthraquinones in Talaromyces islandicus.

    Fukaya, Mitsunori / Ozaki, Taro / Minami, Atsushi / Oikawa, Hideaki

    Bioscience, biotechnology, and biochemistry

    2022  Volume 86, Issue 4, Page(s) 435–443

    Abstract: Talaromyces islandicus is a unique fungus that produces more than 20 numbers of anthraquinones (AQs) and their dimeric natural products, bisanthraquinones (BQs). These compounds share a 9,10-anthracenedione core derived from emodin. The biosynthetic ... ...

    Abstract Talaromyces islandicus is a unique fungus that produces more than 20 numbers of anthraquinones (AQs) and their dimeric natural products, bisanthraquinones (BQs). These compounds share a 9,10-anthracenedione core derived from emodin. The biosynthetic pathway of emodin has been firmly established, while that of other AQs and BQs is still unclear. In this study, we identified the biosynthetic gene clusters for chrysophanol and skyrin. The function of key modification enzymes was examined by performing biotransformation experiments and in vitro enzymatic reactions with emodin and its derivatives, allowing us to propose a mechanism for the modification reactions. The present study provides insight into the biosynthesis of AQs and BQs in T. islandicus.
    MeSH term(s) Anthraquinones/metabolism ; Biotransformation ; Emodin ; Talaromyces/metabolism
    Chemical Substances Anthraquinones ; Emodin (KA46RNI6HN)
    Language English
    Publishing date 2022-02-15
    Publishing country England
    Document type Journal Article
    ZDB-ID 1106450-x
    ISSN 1347-6947 ; 0916-8451
    ISSN (online) 1347-6947
    ISSN 0916-8451
    DOI 10.1093/bbb/zbac009
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    Zs.A 4647: Show issues Location:
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    Jg. 1995 - 2021: Lesesall (2.OG)
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  7. Article ; Online: Recent advances in the biosynthesis of ribosomally synthesized and posttranslationally modified peptides of fungal origin.

    Ozaki, Taro / Minami, Atsushi / Oikawa, Hideaki

    The Journal of antibiotics

    2022  Volume 76, Issue 1, Page(s) 3–13

    Abstract: Ribosomally synthesized and posttranslationally modified peptides (RiPPs) are growing class of natural products with potent biological activities. Although the core scaffolds of RiPPs are composed of proteinogenic amino acids, remarkable structural ... ...

    Abstract Ribosomally synthesized and posttranslationally modified peptides (RiPPs) are growing class of natural products with potent biological activities. Although the core scaffolds of RiPPs are composed of proteinogenic amino acids, remarkable structural diversity is generated through posttranslational modifications (PTMs) of precursor peptides. In addition, ribosomal origin of biosynthetic precursors enables supply of its analogs through genetic approach such as site-directed mutagenesis on corresponding genes. As PTM enzymes often exhibit substrate tolerance, RiPP biosynthetic machineries are considered as efficient tools for generation of unique peptide derivatives. RiPP pathways are distributed among all domains of life and those derived from bacteria and plants have been known for decades. In contrast, fungal RiPPs (F-RiPPs) have fewer examples. Amatoxins and omphalotins are F-RiPPs produced by Basidiomycota fungi. In the biosynthesis of these compounds, macrocyclization by prolyl oligopeptidase homologs and N-methylations of back bone amides have been characterized, respectively. Ustiloxins and related compounds are another group of F-RiPPs with characteristic macrocyclic ethers. UstYa family proteins, which are fungi-specific putative oxidases, have been identified as common proteins involved in PTMs of these compounds. Despite a limited number of characterized examples, recent progress in sequencing of fungal genomes indicated that a number of RiPP pathways are hidden in fungal resources, making F-RiPPs as attractive target for genome mining studies while more detailed understandings of key biosynthetic enzymes are still necessary. This review seeks to describe recent advances on the F-RiPP biosynthesis with slight emphasis on the function of UstYa family proteins.
    MeSH term(s) Ribosomes/genetics ; Peptides/chemistry ; Genes, Fungal ; Biological Products/chemistry ; Protein Processing, Post-Translational
    Chemical Substances Peptides ; Biological Products
    Language English
    Publishing date 2022-11-24
    Publishing country England
    Document type Journal Article ; Review ; Research Support, Non-U.S. Gov't
    ZDB-ID 390800-8
    ISSN 1881-1469 ; 0021-8820 ; 0368-3532
    ISSN (online) 1881-1469
    ISSN 0021-8820 ; 0368-3532
    DOI 10.1038/s41429-022-00576-w
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    Zs.A 207: Show issues Location:
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  8. Article ; Online: Bioinformatics-Guided Reconstitution of Biosynthetic Machineries of Fungal Eremophilane Sesquiterpenes.

    Sato, Yoshiro / Shi, Xinge / Ye, Ying / Domon, Saori / Takino, Junya / Ozaki, Taro / Liu, Chengwei / Oikawa, Hideaki / Minami, Atsushi

    ACS chemical biology

    2024  Volume 19, Issue 4, Page(s) 861–865

    Abstract: Eremophilanes exhibit diverse biological activities and chemical structures. This study reports the bioinformatics-guided reconstitution of the biosynthetic machinery of fungal eremophilanes, eremofortin C and sporogen-AO1, to elucidate their ... ...

    Abstract Eremophilanes exhibit diverse biological activities and chemical structures. This study reports the bioinformatics-guided reconstitution of the biosynthetic machinery of fungal eremophilanes, eremofortin C and sporogen-AO1, to elucidate their biosynthetic pathways. Their biosyntheses include P450-catalyzed multistep oxidation and enzyme-catalyzed isomerization by the DUF3237 family protein. Successful characterization of six P450s enabled us to discuss the functions of eremophilane P450s in putative eremophilane biosynthetic gene clusters, providing opportunities to understand the oxidative modification pathways of fungal eremophilanes.
    MeSH term(s) Sesquiterpenes/chemistry ; Polycyclic Sesquiterpenes ; Oxidation-Reduction
    Chemical Substances Sesquiterpenes ; Polycyclic Sesquiterpenes
    Language English
    Publishing date 2024-04-03
    Publishing country United States
    Document type Journal Article
    ISSN 1554-8937
    ISSN (online) 1554-8937
    DOI 10.1021/acschembio.4c00040
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  9. Article ; Online: Structure and biosynthesis of the ribosomal lipopeptide antibiotic albopeptins.

    Oikawa, Hideaki / Mizunoue, Yusuke / Nakamura, Takemichi / Fukushi, Eri / Yulu, Jiang / Ozaki, Taro / Minami, Atsushi

    Bioscience, biotechnology, and biochemistry

    2022  Volume 86, Issue 6, Page(s) 717–723

    Abstract: Albopeptins produced by Streptomyces albofaciens JC-82-120 were isolated as effective antibiotics for plant pathogenetic disease in 1986. However, their unusual physicochemical properties hampered the determination of their chemical structures. In this ... ...

    Abstract Albopeptins produced by Streptomyces albofaciens JC-82-120 were isolated as effective antibiotics for plant pathogenetic disease in 1986. However, their unusual physicochemical properties hampered the determination of their chemical structures. In this report, we describe our efforts to elucidate their structures. Initially, the structure of an unusual C13-fatty acid with an N-hydroxyguanidyl group was determined using degradation and chemical synthesis. After the linear portion of the octapeptide core was constructed based on the 2D-NMR data, the final assembly of the unusual structure, including the sulfoxide bridge, was achieved through the analysis of detailed NMR data. The proposed structure of albopeptin B was supported by MS/MS data, which also enabled us to determine the structure of 5 albopeptin family members. Bioinformatics analysis of the genomic data of the producer strain further led us to propose that their biosynthetic pathway is similar to the ribosomally derived lanthipeptides possessing a long-chain fatty acid.
    MeSH term(s) Anti-Bacterial Agents/chemistry ; Biosynthetic Pathways/genetics ; Fatty Acids ; Lipopeptides ; Multigene Family ; Tandem Mass Spectrometry
    Chemical Substances Anti-Bacterial Agents ; Fatty Acids ; Lipopeptides
    Language English
    Publishing date 2022-03-13
    Publishing country England
    Document type Journal Article
    ZDB-ID 1106450-x
    ISSN 1347-6947 ; 0916-8451
    ISSN (online) 1347-6947
    ISSN 0916-8451
    DOI 10.1093/bbb/zbac039
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  10. Article ; Online: Stepwise cyclopropanation on the polycyclopropanated polyketide formation in jawsamycin biosynthesis.

    Hiratsuka, Tomoshige / Suzuki, Hideaki / Minami, Atsushi / Oikawa, Hideaki

    Organic & biomolecular chemistry

    2017  Volume 15, Issue 5, Page(s) 1076–1079

    Abstract: Jawsamycin is a polyketide-nucleoside hybrid with a unique polycyclopropane moiety on a single polyketide chain. The unexpected isolation of cyclopropane deficient jawsamycin analogs allowed us to propose a stepwise cyclopropanation mechanism for the ... ...

    Abstract Jawsamycin is a polyketide-nucleoside hybrid with a unique polycyclopropane moiety on a single polyketide chain. The unexpected isolation of cyclopropane deficient jawsamycin analogs allowed us to propose a stepwise cyclopropanation mechanism for the enzymatic synthesis of this polyketide. The concise timing of the cyclopropanation could be regulated by a delicate balance between reaction rates of the condensation and cyclopropanation reactions.
    Language English
    Publishing date 2017-02-01
    Publishing country England
    Document type Journal Article
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/c6ob02675c
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