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Title: Molecular Genetic Characterization of Terreic Acid Pathway in Aspergillus terreus

Journal Article · · Organic Letters
DOI:https://doi.org/10.1021/ol502242a· OSTI ID:1167618
 [1];  [1];  [2];  [3]
  1. Univ. of Southern California, Los Angeles, CA (United States). Dept. of Pharmacology and Pharmaceutical Sciences
  2. Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
  3. Univ. of Southern California, Los Angeles, CA (United States). Dept. of Pharmacology and Pharmaceutical Sciences; Univ. of Southern California, Los Angeles, CA (United States). Dept. of Chemistry

Terreic acid is a natural product derived from 6-methylsalicylic acid (6-MSA). A compact gene cluster for its biosynthesis was characterized. Isolation of the intermediates and shunt products from the mutant strains, in combined with bioinformatic analyses, allowed us to propose a biosynthetic pathway for terreic acid. Lastly, defining the pathway and the genes involved will facilitate the engineering of this molecule with interesting antimicrobial and antitumor bioactivities.

Research Organization:
Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)
Sponsoring Organization:
USDOE Office of Energy Efficiency and Renewable Energy (EERE), Sustainable Transportation Office. Bioenergy Technologies Office
Grant/Contract Number:
AC05-76RL01830; PO1GM084077; 1136903
OSTI ID:
1167618
Report Number(s):
PNNL-SA-102991; BM0101020
Journal Information:
Organic Letters, Vol. 16, Issue 20; ISSN 1523-7060
Publisher:
American Chemical SocietyCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 24 works
Citation information provided by
Web of Science

References (23)

Hidden Function of Catalytic Domain in 6-Methylsalicylic Acid Synthase for Product Release journal May 2010
Molecular cloning and functional characterization of two CYP619 cytochrome P450s involved in biosynthesis of patulin in Aspergillus clavatus journal May 2009
Biosynthesis and Toxicological Effects of Patulin journal April 2010
Quinone epoxides. V. 1 The biosynthesis of terreic acid journal November 1969
Flavipucine [3′-isovaleryl-6-methylpyridine-3-spiro-2′-oxiran-2(1H),4(3H)-dione], an antibiotic from Aspergillus flavipes journal January 1972
Cloning of the polyketide synthase gene atX from Aspergillus terreus and its identification as the 6-Methylsalicylic acid synthase gene by heterologous expression journal November 1996
Fungal secondary metabolism — from biochemistry to genomics journal December 2005
Molecular and Chemical Characterization of the Biosynthesis of the 6-MSA-Derived Meroterpenoid Yanuthone D in Aspergillus niger journal April 2014
Application of an Efficient Gene Targeting System Linking Secondary Metabolites to their Biosynthetic Genes in Aspergillus terreus journal June 2013
Genetic, molecular, and biochemical basis of fungal tropolone biosynthesis journal April 2012
Targeting BTK with Ibrutinib in Relapsed Chronic Lymphocytic Leukemia journal July 2013
Purification and Characterization of Versicolorin B Synthase from Aspergillus parasiticus . Catalysis of the Stereodifferentiating Cyclization in Aflatoxin Biosynthesis Essential to DNA Interaction journal January 1996
Terreic acid, a quinone epoxide inhibitor of Bruton's tyrosine kinase journal March 1999
TRI12, a trichothecene efflux pump from Fusarium sporotrichioides: gene isolation and expression in yeast journal August 1999
Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis journal January 2014
Two Separate Gene Clusters Encode the Biosynthetic Pathway for the Meroterpenoids Austinol and Dehydroaustinol in Aspergillus nidulans journal February 2012
The biosynthesis of terreic acid journal January 1968
Microbial genome mining answers longstanding biosynthetic questions journal May 2012
Culture-based and sequence-based insights into biosynthesis of secondary metabolites by Aspergillus terreus ATCC 20542 journal April 2014
A Mechanism-Driven Treatment for Chronic Lymphocytic Leukemia? journal July 2013
Terbinafine Resistance Mediated by Salicylate 1-Monooxygenase in Aspergillus nidulans journal September 2004
Salicylate Hydroxylase, a Monooxygenase Requiring Flavin Adenine Dinucleotide journal August 1965
The Mechanism of Formation of β-Ketoadipic acid by Bacteria journal October 1954

Cited By (10)

Discovery of McrA, a master regulator of Aspergillus secondary metabolism: McrA regulates Aspergillus secondary metabolism journal November 2016
Bacillus subtilis PTA-271 Counteracts Botryosphaeria Dieback in Grapevine, Triggering Immune Responses and Detoxification of Fungal Phytotoxins journal January 2019
Heterologous pathway assembly reveals molecular steps of fungal terreic acid biosynthesis journal February 2018
Chemodiversity in the genus Aspergillus journal August 2015
Recent advances in the genome mining of Aspergillus secondary metabolites (covering 2012–2018) journal January 2019
Biodiversity, Anti-Trypanosomal Activity Screening, and Metabolomic Profiling of Actinomycetes Isolated from Mediterranean Sponges journal September 2015
Secondary metabolism in Penicillium expansum : Emphasis on recent advances in patulin research journal June 2017
Recent advances in genome mining of secondary metabolites in Aspergillus terreus journal December 2014
Global analysis of biosynthetic gene clusters reveals vast potential of secondary metabolite production in Penicillium species journal April 2017
Biosynthetic gene clusters and the evolution of fungal chemodiversity journal January 2020

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