Literature DB >> 27960349

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

Li Li1, Peiyuan Yu, Man-Cheng Tang, Yi Zou, Shu-Shan Gao, Yiu-Sun Hung, Muxun Zhao, Kenji Watanabe2, K N Houk, Yi Tang.   

Abstract

The trans-decalin structure formed by intramolecular Diels-Alder cycloaddition is widely present among bioactive natural products isolated from fungi. We elucidated the concise three-enzyme biosynthetic pathway of the cytotoxic myceliothermophin and biochemically characterized the Diels-Alderase that catalyzes the formation of trans-decalin from an acyclic substrate. Computational studies of the reaction mechanism rationalize both the substrate and stereoselectivity of the enzyme.

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Year:  2016        PMID: 27960349      PMCID: PMC5323083          DOI: 10.1021/jacs.6b10452

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


  25 in total

Review 1.  Recent advances in understanding the enzymatic reactions of [4+2] cycloaddition and spiroketalization.

Authors:  Qingfei Zheng; Zhenhua Tian; Wen Liu
Journal:  Curr Opin Chem Biol       Date:  2016-02-09       Impact factor: 8.822

Review 2.  Recent advances in natural product synthesis by using intramolecular Diels-Alder reactions.

Authors:  Ken-Ichi Takao; Ryosuke Munakata; Kin-ichi Tadano
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

3.  Distinct mechanisms for spiro-carbon formation reveal biosynthetic pathway crosstalk.

Authors:  Yuta Tsunematsu; Noriyasu Ishikawa; Daigo Wakana; Yukihiro Goda; Hiroshi Noguchi; Hisao Moriya; Kinya Hotta; Kenji Watanabe
Journal:  Nat Chem Biol       Date:  2013-10-13       Impact factor: 15.040

4.  Ascosalipyrrolidinone A, an antimicrobial alkaloid, from the obligate marine fungus Ascochyta salicorniae.

Authors:  C Osterhage; R Kaminsky; G M König; A D Wright
Journal:  J Org Chem       Date:  2000-10-06       Impact factor: 4.354

Review 5.  Recent advances of Diels-Alderases involved in natural product biosynthesis.

Authors:  Atsushi Minami; Hideaki Oikawa
Journal:  J Antibiot (Tokyo)       Date:  2016-06-15       Impact factor: 2.649

6.  An enzymatic [4+2] cyclization cascade creates the pentacyclic core of pyrroindomycins.

Authors:  Zhenhua Tian; Peng Sun; Yan Yan; Zhuhua Wu; Qingfei Zheng; Shuaixiang Zhou; Hua Zhang; Futao Yu; Xinying Jia; Dandan Chen; Attila Mándi; Tibor Kurtán; Wen Liu
Journal:  Nat Chem Biol       Date:  2015-03-02       Impact factor: 15.040

7.  Antifungal substances against pathogenic fungi, talaroconvolutins, from talaromyces convolutus.

Authors:  S Suzuki; T Hosoe; K Nozawa; K i Kawai; T Yaguchi; S Udagawa
Journal:  J Nat Prod       Date:  2000-06       Impact factor: 4.050

8.  Codinaeopsin, an antimalarial fungal polyketide.

Authors:  Renee Kontnik; Jon Clardy
Journal:  Org Lett       Date:  2008-08-13       Impact factor: 6.005

9.  Thioesterase-like role for fungal PKS-NRPS hybrid reductive domains.

Authors:  James W Sims; Eric W Schmidt
Journal:  J Am Chem Soc       Date:  2008-07-25       Impact factor: 15.419

10.  Biosynthesis of versipelostatin: identification of an enzyme-catalyzed [4+2]-cycloaddition required for macrocyclization of spirotetronate-containing polyketides.

Authors:  Takuya Hashimoto; Junko Hashimoto; Kuniko Teruya; Takashi Hirano; Kazuo Shin-ya; Haruo Ikeda; Hung-wen Liu; Makoto Nishiyama; Tomohisa Kuzuyama
Journal:  J Am Chem Soc       Date:  2015-01-05       Impact factor: 15.419

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  26 in total

1.  Enzymatic Intermolecular Hetero-Diels-Alder Reaction in the Biosynthesis of Tropolonic Sesquiterpenes.

Authors:  Qibin Chen; Jie Gao; Cooper Jamieson; Jiawang Liu; Masao Ohashi; Jian Bai; Daojian Yan; Bingyu Liu; Yongsheng Che; Yanan Wang; K N Houk; Youcai Hu
Journal:  J Am Chem Soc       Date:  2019-09-03       Impact factor: 15.419

Review 2.  Recent Advances in Enzymatic Complexity Generation: Cyclization Reactions.

Authors:  Christopher T Walsh; Yi Tang
Journal:  Biochemistry       Date:  2017-12-20       Impact factor: 3.162

Review 3.  The expanding world of biosynthetic pericyclases: cooperation of experiment and theory for discovery.

Authors:  Cooper S Jamieson; Masao Ohashi; Fang Liu; Yi Tang; K N Houk
Journal:  Nat Prod Rep       Date:  2019-05-22       Impact factor: 13.423

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.  In the fungus where it happens: History and future propelling Aspergillus nidulans as the archetype of natural products research.

Authors:  Lindsay K Caesar; Neil L Kelleher; Nancy P Keller
Journal:  Fungal Genet Biol       Date:  2020-10-06       Impact factor: 3.495

6.  FAD-dependent enzyme-catalysed intermolecular [4+2] cycloaddition in natural product biosynthesis.

Authors:  Lei Gao; Cong Su; Xiaoxia Du; Ruishan Wang; Shuming Chen; Yu Zhou; Chengwei Liu; Xiaojing Liu; Runze Tian; Liyun Zhang; Kebo Xie; She Chen; Qianqian Guo; Lanping Guo; Yoshio Hano; Manabu Shimazaki; Atsushi Minami; Hideaki Oikawa; Niu Huang; K N Houk; Luqi Huang; Jungui Dai; Xiaoguang Lei
Journal:  Nat Chem       Date:  2020-05-25       Impact factor: 24.427

7.  Enzyme-Catalyzed Inverse-Electron Demand Diels-Alder Reaction in the Biosynthesis of Antifungal Ilicicolin H.

Authors:  Zhuan Zhang; Cooper S Jamieson; Yi-Lei Zhao; Dehai Li; Masao Ohashi; K N Houk; Yi Tang
Journal:  J Am Chem Soc       Date:  2019-03-26       Impact factor: 15.419

8.  Genome-Mined Diels-Alderase Catalyzes Formation of the cis-Octahydrodecalins of Varicidin A and B.

Authors:  Dan Tan; Cooper S Jamieson; Masao Ohashi; Man-Cheng Tang; K N Houk; Yi Tang
Journal:  J Am Chem Soc       Date:  2019-01-08       Impact factor: 15.419

9.  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

10.  Structural insights into enzymatic [4+2] aza-cycloaddition in thiopeptide antibiotic biosynthesis.

Authors:  Dillon P Cogan; Graham A Hudson; Zhengan Zhang; Taras V Pogorelov; Wilfred A van der Donk; Douglas A Mitchell; Satish K Nair
Journal:  Proc Natl Acad Sci U S A       Date:  2017-11-20       Impact factor: 11.205

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