Literature DB >> 29185768

Focused Genome Mining of Structurally Related Sesterterpenes: Enzymatic Formation of Enantiomeric and Diastereomeric Products.

Koji Narita1, Hajime Sato2,3,4, Atsushi Minami1, Kosei Kudo1, Lei Gao1,5, Chengwei Liu1, Taro Ozaki1, Motoichiro Kodama6, Xiaoguang Lei5, Tohru Taniguchi7, Kenji Monde7, Mami Yamazaki4, Masanobu Uchiyama2,3, Hideaki Oikawa1.   

Abstract

Heterologous expression of four clade-A bifunctional terpene synthases (BFTSs), giving di/sesterterpenes with unique polycyclic carbon skeletons such as sesterfisherol, enabled the isolation of the sesterterpenes Bm1, Bm2, Bm3, and Pb1. Their structures suggested that formation of the products occurs via various diastereomeric carbocation intermediates, allowing the proposal that clade-A BFTSs catalyze three-step cyclizations using several stereofacial combinations of allylic cation-olefin pairs in the corresponding intermediates to generate various stereoisomers.

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Year:  2017        PMID： 29185768     DOI： 10.1021/acs.orglett.7b03418

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


  10 in total

1.  Schultriene and nigtetraene: two sesterterpenes characterized from pathogenetic fungi via genome mining approach.

Authors:  Lan Jiang; Huanting Yang; Xue Zhang; Xiaoying Li; Kangjie Lv; Weiyan Zhang; Guoliang Zhu; Chengwei Liu; Yongheng Wang; Tom Hsiang; Lixin Zhang; Xueting Liu
Journal:  Appl Microbiol Biotechnol       Date:  2022-08-30       Impact factor: 5.560

2.  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

3.  Inherent atomic mobility changes in carbocation intermediates during the sesterterpene cyclization cascade.

Authors:  Hajime Sato; Takaaki Mitsuhashi; Mami Yamazaki; Ikuro Abe; Masanobu Uchiyama
Journal:  Beilstein J Org Chem       Date:  2019-08-07       Impact factor: 2.883

4.  Enzymatic Synthesis of Variediene Analogs.

Authors:  Lin-Fu Liang; Jeroen S Dickschat
Journal:  Chemistry       Date:  2022-02-09       Impact factor: 5.020

5.  Mechanism of the Bifunctional Multiple Product Sesterterpene Synthase AcAS from Aspergillus calidoustus.

Authors:  Zhiyang Quan; Anwei Hou; Bernd Goldfuss; Jeroen S Dickschat
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-04       Impact factor: 16.823

6.  Identification and Characterization of a Cryptic Bifunctional Type I Diterpene Synthase Involved in Talaronoid Biosynthesis from a Marine-Derived Fungus.

Authors:  Peng Zhang; Guangwei Wu; Stephanie C Heard; Changshan Niu; Stephen A Bell; Fengli Li; Ying Ye; Yonghui Zhang; Jaclyn M Winter
Journal:  Org Lett       Date:  2022-09-20       Impact factor: 6.072

7.  Theoretical Study of Sesterfisherol Biosynthesis: Computational Prediction of Key Amino Acid Residue in Terpene Synthase.

Authors:  Hajime Sato; Koji Narita; Atsushi Minami; Mami Yamazaki; Chao Wang; Hironori Suemune; Shingo Nagano; Takeo Tomita; Hideaki Oikawa; Masanobu Uchiyama
Journal:  Sci Rep       Date:  2018-02-06       Impact factor: 4.379

8.  The Biosynthetic Gene Cluster for Sestermobaraenes-Discovery of a Geranylfarnesyl Diphosphate Synthase and a Multiproduct Sesterterpene Synthase from Streptomyces mobaraensis.

Authors:  Anwei Hou; Jeroen S Dickschat
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-31       Impact factor: 15.336

9.  Heterologous production of fungal natural products: Reconstitution of biosynthetic gene clusters in model host Aspergillus oryzae.

Authors:  Hideaki Oikawa
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2020       Impact factor: 3.493

10.  Systematic mining of fungal chimeric terpene synthases using an efficient precursor-providing yeast chassis.

Authors:  Rong Chen; Qidong Jia; Xin Mu; Ben Hu; Xiang Sun; Zixin Deng; Feng Chen; Guangkai Bian; Tiangang Liu
Journal:  Proc Natl Acad Sci U S A       Date:  2021-07-20       Impact factor: 11.205
  10 in total

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