Literature DB >> 29388775

Premutilin Synthase: Ring Rearrangement by a Class II Diterpene Cyclase.

Meimei Xu1, Meirong Jia1, Young J Hong2, Xihou Yin3, Dean J Tantillo2, Philip J Proteau3, Reuben J Peters1.   

Abstract

Biosynthesis of the complex diterpenoid antibiotic pleuromutilin relies on a bifunctional (di)terpene synthase, and here site-directed mutagenesis was used to knockout either of the two active sites. This enabled characterization of the novel ring contracted intermediate produced by the initiating class II diterpene cyclase active site. Quantum chemical calculations further indicate the importance of reactant configuration for this intriguing ring rearrangement.

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Year:  2018        PMID： 29388775      PMCID： PMC5848098          DOI： 10.1021/acs.orglett.8b00121

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


  21 in total

1.  Enzyme Mechanisms for Polycyclic Triterpene Formation.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-08-18       Impact factor: 15.336

Review 2.  Two rings in them all: the labdane-related diterpenoids.

Authors:  Reuben J Peters
Journal:  Nat Prod Rep       Date:  2010-10-01       Impact factor: 13.423

3.  Probing the role of the DXDD motif in Class II diterpene cyclases.

Authors:  Sladjana Prisic; Jianjun Xu; Robert M Coates; Reuben J Peters
Journal:  Chembiochem       Date:  2007-05-25       Impact factor: 3.164

4.  A modular approach for facile biosynthesis of labdane-related diterpenes.

Authors:  Anthony Cyr; P Ross Wilderman; Mara Determan; Reuben J Peters
Journal:  J Am Chem Soc       Date:  2007-05-05       Impact factor: 15.419

5.  Studies on the later stage of the biosynthesis of pleuromutilin.

Authors:  Tae Tsukagoshi; Tetsuo Tokiwano; Hideaki Oikawa
Journal:  Biosci Biotechnol Biochem       Date:  2007-12-07       Impact factor: 2.043

6.  Mycobacterium tuberculosis H37Rv3377c encodes the diterpene cyclase for producing the halimane skeleton.

Authors:  Chiaki Nakano; Tomoo Okamura; Tsutomu Sato; Tohru Dairi; Tsutomu Hoshino
Journal:  Chem Commun (Camb)       Date:  2005-01-04       Impact factor: 6.222

7.  Trinuclear Metal Clusters in Catalysis by Terpenoid Synthases.

Authors:  Julie A Aaron; David W Christianson
Journal:  Pure Appl Chem       Date:  2010       Impact factor: 2.453

8.  Biosynthetic Machinery of Diterpene Pleuromutilin Isolated from Basidiomycete Fungi.

Authors:  Momoka Yamane; Atsushi Minami; Chengwei Liu; Taro Ozaki; Ichiro Takeuchi; Tae Tsukagoshi; Tetsuo Tokiwano; Katsuya Gomi; Hideaki Oikawa
Journal:  Chembiochem       Date:  2017-10-23       Impact factor: 3.164

9.  Functional analysis of eubacterial diterpene cyclases responsible for biosynthesis of a diterpene antibiotic, terpentecin.

Authors:  Yoshimitsu Hamano; Tomohisa Kuzuyama; Nobuya Itoh; Kazuo Furihata; Haruo Seto; Tohru Dairi
Journal:  J Biol Chem       Date:  2002-07-22       Impact factor: 5.157

10.  Molecular and functional evolution of the fungal diterpene synthase genes.

Authors:  Marc J C Fischer; Camille Rustenhloz; Véronique Leh-Louis; Guy Perrière
Journal:  BMC Microbiol       Date:  2015-10-19       Impact factor: 3.605
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  6 in total

1.  Combinatorial biosynthesis and the basis for substrate promiscuity in class I diterpene synthases.

Authors:  Meirong Jia; Sambit K Mishra; Samuel Tufts; Robert L Jernigan; Reuben J Peters
Journal:  Metab Eng       Date:  2019-06-17       Impact factor: 9.783

2.  Catalytic Bases and Stereocontrol in Lamiaceae Class II Diterpene Cyclases.

Authors:  Samuel Schulte; Kevin C Potter; Cody Lemke; Reuben J Peters
Journal:  Biochemistry       Date:  2018-05-31       Impact factor: 3.162

3.  Biocatalytic One-Carbon Ring Expansion of Aziridines to Azetidines via a Highly Enantioselective [1,2]-Stevens Rearrangement.

Authors:  David C Miller; Ravi G Lal; Luca A Marchetti; Frances H Arnold
Journal:  J Am Chem Soc       Date:  2022-03-08       Impact factor: 16.383

4.  Genome-guided investigation of anti-inflammatory sesterterpenoids with 5-15 trans-fused ring system from phytopathogenic fungi.

Authors:  Lan Jiang; Guoliang Zhu; Jianying Han; Chengjian Hou; Xue Zhang; Zhixin Wang; Weize Yuan; Kangjie Lv; Zhanren Cong; Xinye Wang; Xiangyin Chen; Loganathan Karthik; Huanting Yang; Xuyuan Wang; Gaoyi Tan; Guang Liu; Liya Zhao; Xuekui Xia; Xiangyang Liu; Shushan Gao; Lei Ma; Mei Liu; Biao Ren; Huanqin Dai; Ronald J Quinn; Tom Hsiang; Jingyu Zhang; Lixin Zhang; Xueting Liu
Journal:  Appl Microbiol Biotechnol       Date:  2021-06-22       Impact factor: 4.813

5.  Magnesium-specific ring expansion/contraction catalysed by the class II diterpene cyclase from pleuromutilin biosynthesis.

Authors:  Cody Lemke; Owen Whitham; Reuben J Peters
Journal:  Org Biomol Chem       Date:  2020-07-29       Impact factor: 3.876

6.  Changing Face: A Key Residue for the Addition of Water by Sclareol Synthase.

Authors:  Meirong Jia; Terrence E O'Brien; Yue Zhang; Justin B Siegel; Dean J Tantillo; Reuben J Peters
Journal:  ACS Catal       Date:  2018-03-08       Impact factor: 13.084
  6 in total

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