Literature DB >> 31621316

Catalase Involved in Oxidative Cyclization of the Tetracyclic Ergoline of Fungal Ergot Alkaloids.

Yongpeng Yao1, Chunyan An1, Declan Evans2, Weiwei Liu1, Wei Wang1,3, Guangzheng Wei1,3, Ning Ding4, K N Houk2, Shu-Shan Gao1.   

Abstract

A dedicated enzyme for the formation of the central C ring in the tetracyclic ergoline of clinically important ergot alkaloids has never been found. Herein, we report a dual role catalase (EasC), unexpectedly using O2 as the oxidant, that catalyzes the oxidative cyclization of the central C ring from a 1,3-diene intermediate. Our study showcases how nature evolves the common catalase for enantioselective C-C bond construction of complex polycyclic scaffolds.

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Year:  2019        PMID: 31621316      PMCID: PMC7592905          DOI: 10.1021/jacs.9b10217

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


  29 in total

1.  Alkaloid cluster gene ccsA of the ergot fungus Claviceps purpurea encodes chanoclavine I synthase, a flavin adenine dinucleotide-containing oxidoreductase mediating the transformation of N-methyl-dimethylallyltryptophan to chanoclavine I.

Authors:  Nicole Lorenz; Jana Olsovská; Miroslav Sulc; Paul Tudzynski
Journal:  Appl Environ Microbiol       Date:  2010-01-29       Impact factor: 4.792

Review 2.  Oxygen Activation and Radical Transformations in Heme Proteins and Metalloporphyrins.

Authors:  Xiongyi Huang; John T Groves
Journal:  Chem Rev       Date:  2017-12-29       Impact factor: 60.622

3.  Ergot cluster-encoded catalase is required for synthesis of chanoclavine-I in Aspergillus fumigatus.

Authors:  Kerry E Goetz; Christine M Coyle; Johnathan Z Cheng; Sarah E O'Connor; Daniel G Panaccione
Journal:  Curr Genet       Date:  2011-03-17       Impact factor: 3.886

Review 4.  Biotechnology and genetics of ergot alkaloids.

Authors:  P Tudzynski; T Correia; U Keller
Journal:  Appl Microbiol Biotechnol       Date:  2001-12       Impact factor: 4.813

Review 5.  Fungal catalases: function, phylogenetic origin and structure.

Authors:  Wilhelm Hansberg; Rodolfo Salas-Lizana; Laura Domínguez
Journal:  Arch Biochem Biophys       Date:  2012-06-12       Impact factor: 4.013

6.  The function of catalase-bound NADPH.

Authors:  H N Kirkman; S Galiano; G F Gaetani
Journal:  J Biol Chem       Date:  1987-01-15       Impact factor: 5.157

Review 7.  Physiological functions of D-amino acid oxidases: from yeast to humans.

Authors:  L Pollegioni; L Piubelli; S Sacchi; M S Pilone; G Molla
Journal:  Cell Mol Life Sci       Date:  2007-06       Impact factor: 9.261

8.  Partial reconstruction of the ergot alkaloid pathway by heterologous gene expression in Aspergillus nidulans.

Authors:  Katy L Ryan; Christopher T Moore; Daniel G Panaccione
Journal:  Toxins (Basel)       Date:  2013-02-22       Impact factor: 4.546

Review 9.  Biosynthetic pathways of ergot alkaloids.

Authors:  Nina Gerhards; Lisa Neubauer; Paul Tudzynski; Shu-Ming Li
Journal:  Toxins (Basel)       Date:  2014-12-10       Impact factor: 4.546

10.  Discovery and Reconstitution of the Cycloclavine Biosynthetic Pathway-Enzymatic Formation of a Cyclopropyl Group.

Authors:  Dorota Jakubczyk; Lorenzo Caputi; Anaëlle Hatsch; Curt A F Nielsen; Melanie Diefenbacher; Jens Klein; Andrea Molt; Hartwig Schröder; Johnathan Z Cheng; Michael Naesby; Sarah E O'Connor
Journal:  Angew Chem Weinheim Bergstr Ger       Date:  2015-02-25
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  6 in total

Review 1.  The role of biocatalysis in the asymmetric synthesis of alkaloids - an update.

Authors:  Emmanuel Cigan; Bettina Eggbauer; Joerg H Schrittwieser; Wolfgang Kroutil
Journal:  RSC Adv       Date:  2021-08-20       Impact factor: 3.361

2.  Beyond the cyclopropyl ring formation: fungal Aj_EasH catalyzes asymmetric hydroxylation of ergot alkaloids.

Authors:  Chunyan An; Fangfang Zhu; Yongpeng Yao; Kexin Zhang; Wei Wang; Jun Zhang; Guangzheng Wei; Yue Xia; Qiang Gao; Shu-Shan Gao
Journal:  Appl Microbiol Biotechnol       Date:  2022-04-07       Impact factor: 4.813

3.  Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis.

Authors:  Kuan-Lin Chen; Chen-Yu Lai; Mai-Truc Pham; Rong-Jie Chein; Yi Tang; Hsiao-Ching Lin
Journal:  Org Lett       Date:  2020-04-03       Impact factor: 6.005

Review 4.  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

5.  Berberine bridge enzyme-like oxidase-catalysed double bond isomerization acts as the pathway switch in cytochalasin synthesis.

Authors:  Jin-Mei Zhang; Xuan Liu; Qian Wei; Chuanteng Ma; Dehai Li; Yi Zou
Journal:  Nat Commun       Date:  2022-01-11       Impact factor: 14.919

6.  A combined strategy for the overproduction of complex ergot alkaloid agroclavine.

Authors:  Zhi-Pu Yu; Chunyan An; Yongpeng Yao; Chang-Yun Wang; Zhoutong Sun; Chengsen Cui; Ling Liu; Shu-Shan Gao
Journal:  Synth Syst Biotechnol       Date:  2022-08-20
  6 in total

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