Literature DB >> 33084237

Revision of the Cyclisation Mechanism for the Diterpene Spiroviolene and Investigations of Its Mass Spectrometric Fragmentation.

Houchao Xu1, Jeroen S Dickschat1.   

Abstract

The diterpene spiroviolene, its diterpene synthase from Streptomyces violens and the experimentally determined terpene cyclisation mechanism were reported in 2017. Recently, the structure of spiroviolene was revised based on a total synthesis, with consequences for the cyclisation mechanism. Herein, a reinvestigation of the terpene cyclisation to spiroviolene and the mass spectrometric fragmentation mechanism investigated by 13 C-labelling experiments are presented.
© 2020 The Authors. ChemBiochem published by Wiley-VCH GmbH.

Entities:  

Keywords:  biosynthesis; enzyme mechanisms; isotopes; mass spectrometry; terpenes

Year:  2020        PMID： 33084237      PMCID： PMC7983979          DOI： 10.1002/cbic.202000682

Source DB:  PubMed          Journal:  Chembiochem        ISSN： 1439-4227            Impact factor:   3.164


  16 in total

1.  Mechanistic Investigations of Two Bacterial Diterpene Cyclases: Spiroviolene Synthase and Tsukubadiene Synthase.

Authors:  Patrick Rabe; Jan Rinkel; Etilia Dolja; Thomas Schmitz; Britta Nubbemeyer; T Hoang Luu; Jeroen S Dickschat
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-31       Impact factor: 15.336

Review 2.  Cyclopentane-forming di/sesterterpene synthases: widely distributed enzymes in bacteria, fungi, and plants.

Authors:  Atsushi Minami; Taro Ozaki; Chengwei Liu; Hideaki Oikawa
Journal:  Nat Prod Rep       Date:  2018-12-12       Impact factor: 13.423

3.  Position-Specific Mass Shift Analysis: A Systematic Method for Investigating the EI-MS Fragmentation Mechanism of epi-Isozizaene.

Authors:  Patrick Rabe; Tim A Klapschinski; Jeroen S Dickschat
Journal:  Chembiochem       Date:  2016-06-02       Impact factor: 3.164

4.  Studies on the biosynthesis of cholesterol. XX. Steric course of decarboxylation of 5-pyrophosphomevalonate and of the carbon to carbon bond formation in the biosynthesis of farnesyl pyrophosphate.

Authors:  J W Cornforth; R H Cornforth; G Popják; L Yengoyan
Journal:  J Biol Chem       Date:  1966-09-10       Impact factor: 5.157

5.  Spirograterpene A, a Tetracyclic Spiro-Diterpene with a Fused 5/5/5/5 Ring System from the Deep-Sea-Derived Fungus Penicillium granulatum MCCC 3A00475.

Authors:  Siwen Niu; Zuo-Wang Fan; Chun-Lan Xie; Qingmei Liu; Zhu-Hua Luo; Guangming Liu; Xian-Wen Yang
Journal:  J Nat Prod       Date:  2017-07-10       Impact factor: 4.050

6.  Diterpene Biosynthesis in Actinomycetes: Studies on Cattleyene Synthase and Phomopsene Synthase.

Authors:  Jan Rinkel; Simon T Steiner; Jeroen S Dickschat
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-24       Impact factor: 15.336

7.  Structures and Biosynthesis of Corvol Ethers--Sesquiterpenes from the Actinomycete Kitasatospora setae.

Authors:  Patrick Rabe; Khomaizon A K Pahirulzaman; Jeroen S Dickschat
Journal:  Angew Chem Int Ed Engl       Date:  2015-03-24       Impact factor: 15.336

8.  Biosynthetic gene-based secondary metabolite screening: a new diterpene, methyl phomopsenonate, from the fungus Phomopsis amygdali.

Authors:  Tomonobu Toyomasu; Akane Kaneko; Tetsuo Tokiwano; Yuya Kanno; Yuri Kanno; Rie Niida; Shigeyoshi Miura; Taiki Nishioka; Chiho Ikeda; Wataru Mitsuhashi; Tohru Dairi; Tomikazu Kawano; Hideaki Oikawa; Nobuo Kato; Takeshi Sassa
Journal:  J Org Chem       Date:  2009-02-20       Impact factor: 4.354

9.  The EIMS fragmentation mechanisms of the sesquiterpenes corvol ethers A and B, epi-cubebol and isodauc-8-en-11-ol.

Authors:  Patrick Rabe; Jeroen S Dickschat
Journal:  Beilstein J Org Chem       Date:  2016-07-05       Impact factor: 2.883

10.  Terpene Synthase Genes Originated from Bacteria through Horizontal Gene Transfer Contribute to Terpenoid Diversity in Fungi.

Authors:  Qidong Jia; Xinlu Chen; Tobias G Köllner; Jan Rinkel; Jianyu Fu; Jessy Labbé; Wangdan Xiong; Jeroen S Dickschat; Jonathan Gershenzon; Feng Chen
Journal:  Sci Rep       Date:  2019-06-25       Impact factor: 4.379
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  2 in total

1.  Engineering of Ancestors as a Tool to Elucidate Structure, Mechanism, and Specificity of Extant Terpene Cyclase.

Authors:  Karen Schriever; Patricia Saenz-Mendez; Reshma Srilakshmi Rudraraju; Natalie M Hendrikse; Elton P Hudson; Antonino Biundo; Robert Schnell; Per-Olof Syrén
Journal:  J Am Chem Soc       Date:  2021-01-26       Impact factor: 15.419

2.  Revision of the Cyclisation Mechanism for the Diterpene Spiroviolene and Investigations of Its Mass Spectrometric Fragmentation.

Authors:  Houchao Xu; Jeroen S Dickschat
Journal:  Chembiochem       Date:  2020-11-10       Impact factor: 3.164
  2 in total

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