Literature DB >> 28926261

Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products.

Man-Cheng Tang, Xiaoqing Cui1, Xueqian He1, Zhuang Ding1, Tianjiao Zhu1, Yi Tang, Dehai Li1,2.   

Abstract

Macrophorins are representative examples of isoprenoid epoxycyclohexenones containing cyclized drimane moieties. We located and characterized the biosynthetic gene cluster of macrophorin from Penicillium terrestris. MacJ encoded by this cluster was characterized to be the first example of a membrane-bound type-II terpene cyclase catalyzing the cyclization of meroterpenoids via direct protonation of the terminal olefinic bond in acyclic yanuthones. The late-stage functionalization and substrate promiscuity of MacJ make it a potential biocatalyst for the synthesis of macrophorin analogues.

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Year:  2017        PMID： 28926261      PMCID： PMC5682560          DOI： 10.1021/acs.orglett.7b02653

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  36 in total

1.  Yanuthones: novel metabolites from a marine isolate of Aspergillus niger.

Authors:  T S Bugni; D Abbanat; V S Bernan; W M Maiese; M Greenstein; R M Van Wagoner; C M Ireland
Journal:  J Org Chem       Date:  2000-10-20       Impact factor: 4.354

2.  Presence of copalyl diphosphate synthase gene in an actinomycete possessing the mevalonate pathway.

Authors:  Takashi Kawasaki; Tomohisa Kuzuyama; Yuko Kuwamori; Nobuyasu Matsuura; Nobuya Itoh; Kazuo Furihata; Haruo Seto; Tohru Dairi
Journal:  J Antibiot (Tokyo)       Date:  2004-11       Impact factor: 2.649

3.  Total Synthesis and Structure Revision of (-)-Siphonodictyal B and Its Biomimetic Conversion into (+)-Liphagal.

Authors:  Adrian W Markwell-Heys; Kevin K W Kuan; Jonathan H George
Journal:  Org Lett       Date:  2015-08-21       Impact factor: 6.005

4.  Discovery of Unclustered Fungal Indole Diterpene Biosynthetic Pathways through Combinatorial Pathway Reassembly in Engineered Yeast.

Authors:  Man-Cheng Tang; Hsiao-Ching Lin; Dehai Li; Yi Zou; Jian Li; Wei Xu; Ralph A Cacho; Maureen E Hillenmeyer; Neil K Garg; Yi Tang
Journal:  J Am Chem Soc       Date:  2015-10-21       Impact factor: 15.419

5.  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

Review 6.  Terpenoid biosynthesis off the beaten track: unconventional cyclases and their impact on biomimetic synthesis.

Authors:  Martin Baunach; Jakob Franke; Christian Hertweck
Journal:  Angew Chem Int Ed Engl       Date:  2014-12-08       Impact factor: 15.336

Review 7.  Unusual chemistries in fungal meroterpenoid biosynthesis.

Authors:  Yudai Matsuda; Takayoshi Awakawa; Takahiro Mori; Ikuro Abe
Journal:  Curr Opin Chem Biol       Date:  2015-11-21       Impact factor: 8.822

8.  The fumagillin biosynthetic gene cluster in Aspergillus fumigatus encodes a cryptic terpene cyclase involved in the formation of β-trans-bergamotene.

Authors:  Hsiao-Ching Lin; Yit-Heng Chooi; Sourabh Dhingra; Wei Xu; Ana M Calvo; Yi Tang
Journal:  J Am Chem Soc       Date:  2013-03-19       Impact factor: 15.419

9.  Rare merosesquiterpenoids from basidiomycete Craterellus odoratus and their inhibition of 11beta-hydroxysteroid dehydrogenases.

Authors:  Ling Zhang; Yu Shen; Fei Wang; Ying Leng; Ji-Kai Liu
Journal:  Phytochemistry       Date:  2009-10-30       Impact factor: 4.072

10.  Epoxyphomalin A and B, prenylated polyketides with potent cytotoxicity from the marine-derived fungus Phoma sp.

Authors:  Ietidal E Mohamed; Harald Gross; Alexander Pontius; Stefan Kehraus; Anja Krick; Gerhard Kelter; Armin Maier; Heinz-Herbert Fiebig; Gabriele M König
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005
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  11 in total

Review 1.  Terpene synthases in disguise: enzymology, structure, and opportunities of non-canonical terpene synthases.

Authors:  Jeffrey D Rudolf; Chin-Yuan Chang
Journal:  Nat Prod Rep       Date:  2020-03-25       Impact factor: 13.423

2.  Marine-Derived Penicillium purpurogenum Reduces Tumor Size and Ameliorates Inflammation in an Erlich Mice Model.

Authors:  Amanda Mara Teles; Leticia Prince Pereira Pontes; Sulayne Janayna Araújo Guimarães; Ana Luiza Butarelli; Gabriel Xavier Silva; Flavia Raquel Fernandes do Nascimento; Geusa Felipa de Barros Bezerra; Carla Junqueira Moragas-Tellis; Rui Miguel Gil da Costa; Marcos Antonio Custódio Neto da Silva; Fernando Almeida-Souza; Kátia da Silva Calabrese; Ana Paula Silva Azevedo-Santos; Maria do Desterro Soares Brandão Nascimento
Journal:  Mar Drugs       Date:  2020-10-29       Impact factor: 5.118

3.  CRISPR-based transcriptional activation tool for silent genes in filamentous fungi.

Authors:  László Mózsik; Mirthe Hoekzema; Niels A W de Kok; Roel A L Bovenberg; Yvonne Nygård; Arnold J M Driessen
Journal:  Sci Rep       Date:  2021-01-13       Impact factor: 4.379

Review 4.  Regulation of Secondary Metabolism in the Penicillium Genus.

Authors:  Christelle El Hajj Assaf; Chrystian Zetina-Serrano; Nadia Tahtah; André El Khoury; Ali Atoui; Isabelle P Oswald; Olivier Puel; Sophie Lorber
Journal:  Int J Mol Sci       Date:  2020-12-12       Impact factor: 5.923

5.  Exploiting the Potential of Meroterpenoid Cyclases to Expand the Chemical Space of Fungal Meroterpenoids.

Authors:  Takaaki Mitsuhashi; Lena Barra; Zachary Powers; Volga Kojasoy; Andrea Cheng; Feng Yang; Yoshimasa Taniguchi; Takashi Kikuchi; Makoto Fujita; Dean J Tantillo; John A Porco; Ikuro Abe
Journal:  Angew Chem Int Ed Engl       Date:  2020-10-22       Impact factor: 15.336

6.  Three previously unrecognised classes of biosynthetic enzymes revealed during the production of xenovulene A.

Authors:  Raissa Schor; Carsten Schotte; Daniel Wibberg; Jörn Kalinowski; Russell J Cox
Journal:  Nat Commun       Date:  2018-05-17       Impact factor: 14.919

7.  Genome mining of cyclodipeptide synthases unravels unusual tRNA-dependent diketopiperazine-terpene biosynthetic machinery.

Authors:  Tingting Yao; Jing Liu; Zengzhi Liu; Tong Li; Huayue Li; Qian Che; Tianjiao Zhu; Dehai Li; Qianqun Gu; Wenli Li
Journal:  Nat Commun       Date:  2018-10-05       Impact factor: 14.919

8.  Immunosuppressant mycophenolic acid biosynthesis employs a new globin-like enzyme for prenyl side chain cleavage.

Authors:  Xiwei Chen; Lu Wang; Jinmei Zhang; Tao Jiang; Changhua Hu; Dehai Li; Yi Zou
Journal:  Acta Pharm Sin B       Date:  2019-06-28       Impact factor: 11.413

9.  Deletion of the Histone Deacetylase HdaA in Endophytic Fungus Penicillium chrysogenum Fes1701 Induces the Complex Response of Multiple Bioactive Secondary Metabolite Production and Relevant Gene Cluster Expression.

Authors:  Zhuang Ding; Haibo Zhou; Xiao Wang; Huiming Huang; Haotian Wang; Ruiyan Zhang; Zhengping Wang; Jun Han
Journal:  Molecules       Date:  2020-08-11       Impact factor: 4.411

Review 10.  New Trends and Future Opportunities in the Enzymatic Formation of C-C, C-N, and C-O bonds.

Authors:  Jack J Sangster; James R Marshall; Nicholas J Turner; Juan Mangas-Sanchez
Journal:  Chembiochem       Date:  2021-11-24       Impact factor: 3.461
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