Literature DB >> 33834778

Biosynthesis of para-Cyclophane-Containing Hirsutellone Family of Fungal Natural Products.

Masao Ohashi, Thomas B Kakule, Man-Cheng Tang, Cooper S Jamieson, Mengting Liu, Yi-Lei Zhao1, Kendall N Houk, Yi Tang.   

Abstract

Hirsutellones are fungal natural products containing a macrocyclic para-cyclophane connected to a decahydrofluorene ring system. We have elucidated the biosynthetic pathway for pyrrocidine B (3) and GKK1032 A2 (4). Two small hypothetical proteins, an oxidoreductase and a lipocalin-like protein, function cooperatively in the oxidative cyclization of the cyclophane, while an additional hypothetical protein in the pyrrocidine pathway catalyzes the exo-specific cycloaddition to form the cis-fused decahydrofluorene.

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Year:  2021        PMID： 33834778      PMCID： PMC8094548          DOI： 10.1021/jacs.1c00098

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  20 in total

1.  Strained cyclophane natural products: macrocyclization at its limits.

Authors:  Tanja Gulder; Phil S Baran
Journal:  Nat Prod Rep       Date:  2012-06-25       Impact factor: 13.423

Review 2.  Oxidative Cyclization in Natural Product Biosynthesis.

Authors:  Man-Cheng Tang; Yi Zou; Kenji Watanabe; Christopher T Walsh; Yi Tang
Journal:  Chem Rev       Date:  2016-12-12       Impact factor: 60.622

Review 3.  Molecular diversity sculpted by fungal PKS-NRPS hybrids.

Authors:  Daniela Boettger; Christian Hertweck
Journal:  Chembiochem       Date:  2012-12-07       Impact factor: 3.164

4.  Collaborative Biosynthesis of Maleimide- and Succinimide-Containing Natural Products by Fungal Polyketide Megasynthases.

Authors:  Michio Sato; Jacob E Dander; Chizuru Sato; Yiu-Sun Hung; Shu-Shan Gao; Man-Cheng Tang; Leibniz Hang; Jaclyn M Winter; Neil K Garg; Kenji Watanabe; Yi Tang
Journal:  J Am Chem Soc       Date:  2017-04-05       Impact factor: 15.419

5.  Synthetic study of pyrrocidines: first entry to the decahydrofluorene core of pyrrocidines.

Authors:  Ryo Tanaka; Kentaro Ohishi; Noriyuki Takanashi; Tomohiko Nagano; Hiroshi Suizu; Takahiro Suzuki; Susumu Kobayashi
Journal:  Org Lett       Date:  2012-08-31       Impact factor: 6.005

6.  Total synthesis of hirsutellone B via Ullmann-type direct 13-membered macrocyclization.

Authors:  Hiromi Uchiro; Ryo Kato; Yuuki Arai; Miki Hasegawa; Yu Kobayakawa
Journal:  Org Lett       Date:  2011-10-31       Impact factor: 6.005

7.  Genome Mining and Assembly-Line Biosynthesis of the UCS1025A Pyrrolizidinone Family of Fungal Alkaloids.

Authors:  Li Li; Man-Cheng Tang; Shoubin Tang; Shushan Gao; Sameh Soliman; Leibniz Hang; Wei Xu; Tao Ye; Kenji Watanabe; Yi Tang
Journal:  J Am Chem Soc       Date:  2018-02-02       Impact factor: 15.419

8.  Biochemical Characterization of a Eukaryotic Decalin-Forming Diels-Alderase.

Authors:  Li Li; Peiyuan Yu; Man-Cheng Tang; Yi Zou; Shu-Shan Gao; Yiu-Sun Hung; Muxun Zhao; Kenji Watanabe; K N Houk; Yi Tang
Journal:  J Am Chem Soc       Date:  2016-11-30       Impact factor: 15.419

9.  Total synthesis of hirsutellone B.

Authors:  K C Nicolaou; David Sarlah; T Robert Wu; Weiqiang Zhan
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Bio-inspired formal synthesis of hirsutellones A-C featuring an electrophilic cyclization triggered by remote Lewis acid-activation.

Authors:  Xu-Wen Li; Alexandre Ear; Lukas Roger; Nassima Riache; Alexandre Deville; Bastien Nay
Journal:  Chemistry       Date:  2013-10-18       Impact factor: 5.236
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  3 in total

1.  Discovery and characterization of a terpene biosynthetic pathway featuring a norbornene-forming Diels-Alderase.

Authors:  Zuodong Sun; Cooper S Jamieson; Masao Ohashi; K N Houk; Yi Tang
Journal:  Nat Commun       Date:  2022-05-11       Impact factor: 17.694

2.  Optimization of Protoplast Preparation and Establishment of Genetic Transformation System of an Arctic-Derived Fungus Eutypella sp.

Authors:  Yaodong Ning; Bo Hu; Haobing Yu; Xiaoyu Liu; Binghua Jiao; Xiaoling Lu
Journal:  Front Microbiol       Date:  2022-04-06       Impact factor: 6.064

3.  Identification of Genetic Diversity, Pyrrocidine-Producing Strains and Transmission Modes of Endophytic Sarocladium zeae Fungi from Zea Crops.

Authors:  Qianhe Liu; Linda J Johnson; Emma R Applegate; Karoline Arfmann; Ruy Jauregui; Anna Larking; Wade J Mace; Paul Maclean; Thomas Walker; Richard D Johnson
Journal:  Microorganisms       Date:  2022-07-14
  3 in total

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