Literature DB >> 30311924

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

Cooper S Jamieson1, Masao Ohashi, Fang Liu, Yi Tang, K N Houk.   

Abstract

Covering: 2000 to 2018 Pericyclic reactions are a distinct class of reactions that have wide synthetic utility. Before the recent discoveries described in this review, enzyme-catalyzed pericyclic reactions were not widely known to be involved in biosynthesis. This situation is changing rapidly. We define the scope of pericyclic reactions, give a historical account of their discoveries as biosynthetic reactions, and provide evidence that there are many enzymes in nature that catalyze pericyclic reactions. These enzymes, the "pericyclases," are the subject of this review.

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Year:  2019        PMID： 30311924      PMCID： PMC6461539          DOI： 10.1039/c8np00075a

Source DB:  PubMed          Journal:  Nat Prod Rep        ISSN： 0265-0568            Impact factor:   13.423


  71 in total

1.  Crystal structure of precorrin-8x methyl mutase.

Authors:  L W Shipman; D Li; C A Roessner; A I Scott; J C Sacchettini
Journal:  Structure       Date:  2001-07-03       Impact factor: 5.006

2.  Shape complementarity, binding-site dynamics, and transition state stabilization: a theoretical study of Diels-Alder catalysis by antibody 1E9.

Authors:  J Chen; Q Deng; R Wang; K Houk; D Hilvert
Journal:  Chembiochem       Date:  2000-11-17       Impact factor: 3.164

3.  An unexpected bispericyclic transition structure leading to 4+2 and 2+4 cycloadducts in the endo dimerization of cyclopentadiene.

Authors:  Pierluigi Caramella; Paolo Quadrelli; Lucio Toma
Journal:  J Am Chem Soc       Date:  2002-02-20       Impact factor: 15.419

4.  Insight into a natural Diels-Alder reaction from the structure of macrophomate synthase.

Authors:  Toyoyuki Ose; Kenji Watanabe; Takashi Mie; Mamoru Honma; Hiromi Watanabe; Min Yao; Hideaki Oikawa; Isao Tanaka
Journal:  Nature       Date:  2003-03-13       Impact factor: 49.962

Review 5.  Chemistry and biology of biosynthetic Diels-Alder reactions.

Authors:  Emily M Stocking; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2003-07-14       Impact factor: 15.336

Review 6.  Enzymatic catalysis of the Diels-Alder reaction in the biosynthesis of natural products.

Authors:  Hideaki Oikawa; Tetsuo Tokiwano
Journal:  Nat Prod Rep       Date:  2004-05-03       Impact factor: 13.423

7.  Total Synthesis of (+/-)-Leporin A.

Authors:  Barry B. Snider; Qing Lu
Journal:  J Org Chem       Date:  1996-04-19       Impact factor: 4.354

8.  The Art and Science of Total Synthesis at the Dawn of the Twenty-First Century.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-01       Impact factor: 15.336

9.  Detailed reaction mechanism of macrophomate synthase. Extraordinary enzyme catalyzing five-step transformation from 2-pyrones to benzoates.

Authors:  K Watanabe; T Mie; A Ichihara; H Oikawa; M Honma
Journal:  J Biol Chem       Date:  2000-12-08       Impact factor: 5.157

10.  The origins of noncovalent catalysis of intermolecular Diels-Alder reactions by cyclodextrins, self-assembling capsules, antibodies, and RNAses.

Authors:  Susanna P Kim; Andrew G Leach; K N Houk
Journal:  J Org Chem       Date:  2002-06-14       Impact factor: 4.354
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  19 in total

1.  Total synthesis of brevianamide A.

Authors:  Robert C Godfrey; Nicholas J Green; Gary S Nichol; Andrew L Lawrence
Journal:  Nat Chem       Date:  2020-04-13       Impact factor: 24.427

2.  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

3.  Thiopeptide Pyridine Synthase TbtD Catalyzes an Intermolecular Formal Aza-Diels-Alder Reaction.

Authors:  Jonathan W Bogart; Albert A Bowers
Journal:  J Am Chem Soc       Date:  2019-01-22       Impact factor: 15.419

4.  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

5.  Byproduct formation during the biosynthesis of spinosyn A and evidence for an enzymatic interplay to prevent its formation.

Authors:  Byung-Sun Jeon; Teng-Yi Huang; Mark W Ruszczycky; Sei-Hyun Choi; Namho Kim; Joseph Livy Franklin; Shang-Cheng Hung; Hung-Wen Liu
Journal:  Tetrahedron       Date:  2021-11-22       Impact factor: 2.388

6.  Computational Prediction and Experimental Validation of a Bridged Cation Intermediate in Akanthomycin Biosynthesis.

Authors:  Cooper S Jamieson; Masao Ohashi; K N Houk; Yi Tang
Journal:  J Am Chem Soc       Date:  2022-03-17       Impact factor: 16.383

7.  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

8.  Crystal Structures of Fsa2 and Phm7 Catalyzing [4 + 2] Cycloaddition Reactions with Reverse Stereoselectivities in Equisetin and Phomasetin Biosynthesis.

Authors:  Changbiao Chi; Zhengdong Wang; Tan Liu; Zhongyi Zhang; Huan Zhou; Annan Li; Hongwei Jin; Hongli Jia; Fuling Yin; Donghui Yang; Ming Ma
Journal:  ACS Omega       Date:  2021-05-06

Review 9.  Biosynthesis and synthetic biology of psychoactive natural products.

Authors:  Cooper S Jamieson; Joshua Misa; Yi Tang; John M Billingsley
Journal:  Chem Soc Rev       Date:  2021-06-21       Impact factor: 60.615

10.  Computational Investigation of the Mechanism of Diels-Alderase PyrI4.

Authors:  Yike Zou; Song Yang; Jacob N Sanders; Wei Li; Peiyuan Yu; Hongbo Wang; Zhijun Tang; Wen Liu; K N Houk
Journal:  J Am Chem Soc       Date:  2020-11-14       Impact factor: 16.383
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