Literature DB >> 23434416

Reconstitution of the early steps of gliotoxin biosynthesis in Aspergillus nidulans reveals the role of the monooxygenase GliC.

Shu-Lin Chang1, Yi-Ming Chiang, Hsu-Hua Yeh, Tung-Kung Wu, Clay C C Wang.   

Abstract

The gliotoxin, a member of the epipolythiodioxopiperazine (ETP), has received considerable attention from the scientific community for its wide range of biological activity. Despite the identification of gliotoxin cluster, however, the sequence of steps in the gliotoxin biosynthesis has remained elusive. As an alternative to the gene knock-out and biochemical approaches used so far, here we report using a heterologous expression approach to determine the sequence of the early steps of gliotoxin biosynthesis in Aspergillus nidulans. We identified the GliC, a monooxygenases that involved in the second step of gliotoxin biosynthesis pathway through the catalyzing the hydroxylation at the α-position of L-Phe.
Copyright © 2013 Elsevier Ltd. All rights reserved.

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Year:  2013        PMID: 23434416      PMCID: PMC3640825          DOI: 10.1016/j.bmcl.2013.01.099

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  18 in total

1.  ANTIVIRAL ACTIVITY OF GLIOTOXIN AND GLIOTOXIN ACETATE.

Authors:  W A RIGHTSEL; H G SCHNEIDER; B J SLOAN; P R GRAF; F A MILLER; O R BARTZ; J EHRLICH; G J DIXON
Journal:  Nature       Date:  1964-12-26       Impact factor: 49.962

2.  Disruption of a nonribosomal peptide synthetase in Aspergillus fumigatus eliminates gliotoxin production.

Authors:  Robert A Cramer; Michael P Gamcsik; Rhea M Brooking; Laura K Najvar; William R Kirkpatrick; Thomas F Patterson; Carl J Balibar; John R Graybill; John R Perfect; Soman N Abraham; William J Steinbach
Journal:  Eukaryot Cell       Date:  2006-06

3.  Structural relationship of epipolythiodioxopiperazines and their immunomodulating activity.

Authors:  A Müllbacher; P Waring; U Tiwari-Palni; R D Eichner
Journal:  Mol Immunol       Date:  1986-02       Impact factor: 4.407

Review 4.  Gliotoxin and related epipolythiodioxopiperazines.

Authors:  P Waring; J Beaver
Journal:  Gen Pharmacol       Date:  1996-12

5.  Characterization of an inducible expression system in Aspergillus nidulans using alcA and tubulin-coding genes.

Authors:  R B Waring; G S May; N R Morris
Journal:  Gene       Date:  1989-06-30       Impact factor: 3.688

6.  Bioinformatic and expression analysis of the putative gliotoxin biosynthetic gene cluster of Aspergillus fumigatus.

Authors:  Donald M Gardiner; Barbara J Howlett
Journal:  FEMS Microbiol Lett       Date:  2005-07-15       Impact factor: 2.742

7.  GliP, a multimodular nonribosomal peptide synthetase in Aspergillus fumigatus, makes the diketopiperazine scaffold of gliotoxin.

Authors:  Carl J Balibar; Christopher T Walsh
Journal:  Biochemistry       Date:  2006-12-19       Impact factor: 3.162

8.  Microwave-assisted solid-phase synthesis of 2,5-diketopiperazines: solvent and resin dependence.

Authors:  Marcus Tullberg; Kristina Luthman; Morten Grøtli
Journal:  J Comb Chem       Date:  2006 Nov-Dec

9.  Self-protection against gliotoxin--a component of the gliotoxin biosynthetic cluster, GliT, completely protects Aspergillus fumigatus against exogenous gliotoxin.

Authors:  Markus Schrettl; Stephen Carberry; Kevin Kavanagh; Hubertus Haas; Gary W Jones; Jennifer O'Brien; Aine Nolan; John Stephens; Orla Fenelon; Sean Doyle
Journal:  PLoS Pathog       Date:  2010-06-10       Impact factor: 6.823

10.  A gene cluster containing two fungal polyketide synthases encodes the biosynthetic pathway for a polyketide, asperfuranone, in Aspergillus nidulans.

Authors:  Yi-Ming Chiang; Edyta Szewczyk; Ashley D Davidson; Nancy Keller; Berl R Oakley; Clay C C Wang
Journal:  J Am Chem Soc       Date:  2009-03-04       Impact factor: 15.419

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  8 in total

1.  Interplay between Gliotoxin Resistance, Secretion, and the Methyl/Methionine Cycle in Aspergillus fumigatus.

Authors:  Rebecca A Owens; Grainne O'Keeffe; Elizabeth B Smith; Stephen K Dolan; Stephen Hammel; Kevin J Sheridan; David A Fitzpatrick; Thomas M Keane; Gary W Jones; Sean Doyle
Journal:  Eukaryot Cell       Date:  2015-07-06

2.  Biosynthetic Cyclization Catalysts for the Assembly of Peptide and Polyketide Natural Products.

Authors:  Maria L Adrover-Castellano; Jennifer J Schmidt; David H Sherman
Journal:  ChemCatChem       Date:  2021-01-28       Impact factor: 5.686

3.  Diketopiperazine Formation in Fungi Requires Dedicated Cyclization and Thiolation Domains.

Authors:  Joshua A Baccile; Henry H Le; Brandon T Pfannenstiel; Jin Woo Bok; Christian Gomez; Eileen Brandenburger; Dirk Hoffmeister; Nancy P Keller; Frank C Schroeder
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-28       Impact factor: 15.336

4.  Comprehensive curation and analysis of fungal biosynthetic gene clusters of published natural products.

Authors:  Yong Fuga Li; Kathleen J S Tsai; Colin J B Harvey; James Jian Li; Beatrice E Ary; Erin E Berlew; Brenna L Boehman; David M Findley; Alexandra G Friant; Christopher A Gardner; Michael P Gould; Jae H Ha; Brenna K Lilley; Emily L McKinstry; Saadia Nawal; Robert C Parry; Kristina W Rothchild; Samantha D Silbert; Michael D Tentilucci; Alana M Thurston; Rebecca B Wai; Yongjin Yoon; Raeka S Aiyar; Marnix H Medema; Maureen E Hillenmeyer; Louise K Charkoudian
Journal:  Fungal Genet Biol       Date:  2016-01-22       Impact factor: 3.495

5.  Integration of In Silico and In Vitro Analysis of Gliotoxin Production Reveals a Narrow Range of Producing Fungal Species.

Authors:  Sergio Redrado; Patricia Esteban; María Pilar Domingo; Concepción Lopez; Antonio Rezusta; Ariel Ramirez-Labrada; Maykel Arias; Julián Pardo; Eva M Galvez
Journal:  J Fungi (Basel)       Date:  2022-03-31

6.  The Epipolythiodiketopiperazine Gene Cluster in Claviceps purpurea: Dysfunctional Cytochrome P450 Enzyme Prevents Formation of the Previously Unknown Clapurines.

Authors:  Julian Dopstadt; Lisa Neubauer; Paul Tudzynski; Hans-Ulrich Humpf
Journal:  PLoS One       Date:  2016-07-08       Impact factor: 3.240

Review 7.  Involvement of Sulfur in the Biosynthesis of Essential Metabolites in Pathogenic Fungi of Animals, Particularly Aspergillus spp.: Molecular and Therapeutic Implications.

Authors:  Aimee M Traynor; Kevin J Sheridan; Gary W Jones; José A Calera; Sean Doyle
Journal:  Front Microbiol       Date:  2019-12-13       Impact factor: 5.640

8.  Interaction of a Novel Zn2Cys6 Transcription Factor DcGliZ with Promoters in the Gliotoxin Biosynthetic Gene Cluster of the Deep-Sea-Derived Fungus Dichotomomyces cejpii.

Authors:  Zi-Lei Huang; Wei Ye; Mu-Zi Zhu; Ya-Li Kong; Sai-Ni Li; Shan Liu; Wei-Min Zhang
Journal:  Biomolecules       Date:  2019-12-29
  8 in total

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