Molecular Genetic Characterization of a Cluster in A. terreus for Biosynthesis of the Meroterpenoid Terretonin

Meroterpenoids are natural products produced from polyketide and terpenoid precursors. A gene targeting system for A. terreus NIH2624 was developed, and a gene cluster for terretonin biosynthesis was characterized. The intermediates and shunt products were isolated from the mutant strains, and a pat...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 14; no. 22; pp. 5684 - 5687
Main Authors Guo, Chun-Jun, Knox, Benjamin P, Chiang, Yi-Ming, Lo, Hsien-Chun, Sanchez, James F, Lee, Kuan-Han, Oakley, Berl R, Bruno, Kenneth S, Wang, Clay C. C
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.11.2012
Amer Chemical Soc
Subjects
Online AccessGet full text

Cover

Loading…
Abstract Meroterpenoids are natural products produced from polyketide and terpenoid precursors. A gene targeting system for A. terreus NIH2624 was developed, and a gene cluster for terretonin biosynthesis was characterized. The intermediates and shunt products were isolated from the mutant strains, and a pathway for terretonin biosynthesis is proposed. Analysis of two meroterpenoid pathways corresponding to terretonin in A. terreus and austinol in A. nidulans reveals that they are closely related evolutionarily.
AbstractList Meroterpenoids are natural products produced from polyketide and terpenoid precursors. A gene targeting system for A. terreus NIH2624 was developed, and a gene cluster for terretonin biosynthesis was characterized. The intermediates and shunt products were isolated from the mutant strains, and a pathway for terretonin biosynthesis is proposed. Analysis of two meroterpenoid pathways corresponding to terretonin in A. terreus and austinol in A. nidulans reveals that they are closely related evolutionarily.
Meroterpenoids are natural products produced from polyketide and terpenoid precursors. A gene targeting system for A. terreus NIH2624 was developed, and a gene cluster for terretonin biosynthesis was characterized. The intermediates and shunt products were isolated from the mutant strains, and a pathway for terretonin biosynthesis is proposed. Analysis of two meroterpenoid pathways corresponding to terretonin in A. terreus and austinol in A. nidulans reveals that they are closely related evolutionarily.Meroterpenoids are natural products produced from polyketide and terpenoid precursors. A gene targeting system for A. terreus NIH2624 was developed, and a gene cluster for terretonin biosynthesis was characterized. The intermediates and shunt products were isolated from the mutant strains, and a pathway for terretonin biosynthesis is proposed. Analysis of two meroterpenoid pathways corresponding to terretonin in A. terreus and austinol in A. nidulans reveals that they are closely related evolutionarily.
Meroterpenoids are natural products produced from polyketide and terpenoid precursors. A gene targeting system for A. terreus NIH2624 was developed and a gene cluster for terretonin biosynthesis was characterized. The intermediates and shunt products were isolated from the mutant strains and a pathway for terretonin biosynthesis is proposed. Analysis of two meroterpenoid pathways corresponding to terretonin in A. terreus and austinol in A. nidulans reveals that they are closely related evolutionarily.
Author Lee, Kuan-Han
Bruno, Kenneth S
Knox, Benjamin P
Guo, Chun-Jun
Lo, Hsien-Chun
Wang, Clay C. C
Oakley, Berl R
Sanchez, James F
Chiang, Yi-Ming
AuthorAffiliation University of Kansas
University of Southern California
Pacific Northwest National Laboratory
Chia Nan University of Pharmacy and Science
AuthorAffiliation_xml – name: University of Kansas
– name: Chia Nan University of Pharmacy and Science
– name: University of Southern California
– name: Pacific Northwest National Laboratory
– name: 4 Graduate Institute of Pharmaceutical Science, Chia Nan University of Pharmacy and Science, Tainan 71710, Taiwan, ROC
– name: 5 Department of Chemistry, College of Letters, Arts, and Sciences, University of Southern California, Los Angeles, CA 90089, USA
– name: 2 Chemical and Biological Process Development Group, Energy and Environment Directorate, Pacific Northwest National Laboratory, Richland, WA 99352, USA
– name: 1 Department of Pharmacology and Pharmaceutical Sciences, School of Pharmacy, University of Southern California, Los Angeles, CA 90089, USA
– name: 3 Department of Molecular Biosciences, University of Kansas, 1200 Sunnyside Ave., Lawrence, KS 66045, USA
Author_xml – sequence: 1
  givenname: Chun-Jun
  surname: Guo
  fullname: Guo, Chun-Jun
– sequence: 2
  givenname: Benjamin P
  surname: Knox
  fullname: Knox, Benjamin P
– sequence: 3
  givenname: Yi-Ming
  surname: Chiang
  fullname: Chiang, Yi-Ming
– sequence: 4
  givenname: Hsien-Chun
  surname: Lo
  fullname: Lo, Hsien-Chun
– sequence: 5
  givenname: James F
  surname: Sanchez
  fullname: Sanchez, James F
– sequence: 6
  givenname: Kuan-Han
  surname: Lee
  fullname: Lee, Kuan-Han
– sequence: 7
  givenname: Berl R
  surname: Oakley
  fullname: Oakley, Berl R
– sequence: 8
  givenname: Kenneth S
  surname: Bruno
  fullname: Bruno, Kenneth S
  email: bruno@pnnl.gov, clayw@usc.edu
– sequence: 9
  givenname: Clay C. C
  surname: Wang
  fullname: Wang, Clay C. C
  email: bruno@pnnl.gov, clayw@usc.edu
BackLink https://www.ncbi.nlm.nih.gov/pubmed/23116177$$D View this record in MEDLINE/PubMed
BookMark eNqNkl9rFDEUxYNU7B998AtIXgRFtk0ymUzmpVCHWgstvtTnkM3cuCmzyZpklPbTm-mug0qhPuVw8zuHy733EO354AGh15QcU8LoSRgqwoRk98_QAa1ZtWhIzfZmLcg-OkzplhBaKu0LtM8qSgVtmgPkr8MAZhx0xBfgITuDu5WO2mSI7l5nFzwOFmvcDWMqNew8PjvGRUUYE7Yh4o8upDufV5Bcmtii8DXEUJgN-OB6fDPROXjnX6LnVg8JXu3eI_T10_lN93lx9eXisju7WmjeirywfelV17aRPdGc1LQnvYVaVobTVghhlhIks6Spe6kBjBDaNnzZc94wznlbHaHTbe5mXK6hN-Bz1IPaRLfW8U4F7dTfP96t1LfwQ1V1JSmbAt7tAmL4PkLKau2SgWHQHsKYFCOU0LapqHwSpaypGBdSTKlv_mxr7uf3PgrwYQv8hGWwyTjwBmaMEFLAEkaLohMt_5_uXH5YZxdGn4v1_dZqYkgpgp1tlKjpqNR8VIU9-Yc1u6wyOjc86ni7dWiT1G0Yoy_LfoT7Baf22Zo
CitedBy_id crossref_primary_10_1021_acs_jnatprod_5b00650
crossref_primary_10_1039_C9MD00054B
crossref_primary_10_1016_j_biotechadv_2018_02_001
crossref_primary_10_1021_jacs_6b10397
crossref_primary_10_1039_D0NP00066C
crossref_primary_10_3390_md11051602
crossref_primary_10_1002_ange_202011171
crossref_primary_10_3390_md15070214
crossref_primary_10_1021_acschembio_7b00003
crossref_primary_10_1016_j_phytol_2019_05_017
crossref_primary_10_1016_j_jbiotec_2014_01_038
crossref_primary_10_1021_ja508127q
crossref_primary_10_1002_ange_201705654
crossref_primary_10_1002_anie_202104014
crossref_primary_10_1039_D4SC05590J
crossref_primary_10_3390_molecules28062722
crossref_primary_10_1016_j_phytochem_2022_113229
crossref_primary_10_1016_j_apsb_2017_12_005
crossref_primary_10_1039_D3NP00004D
crossref_primary_10_1111_1462_2920_14333
crossref_primary_10_1016_j_fgb_2018_08_001
crossref_primary_10_1002_cctc_202401495
crossref_primary_10_1038_nchembio_2443
crossref_primary_10_1021_jacs_6b08424
crossref_primary_10_1002_ejoc_201701335
crossref_primary_10_1016_j_fgb_2022_103694
crossref_primary_10_1016_j_fgb_2024_103892
crossref_primary_10_1021_ol401384v
crossref_primary_10_1021_ja3123653
crossref_primary_10_1002_anie_202011171
crossref_primary_10_1039_C5NP00090D
crossref_primary_10_3389_fmicb_2014_00717
crossref_primary_10_1016_j_tet_2013_07_029
crossref_primary_10_1002_anie_201705654
crossref_primary_10_1007_s00253_021_11312_z
crossref_primary_10_1016_j_chembiol_2014_03_010
crossref_primary_10_1038_ja_2016_54
crossref_primary_10_1016_j_phytochem_2021_113011
crossref_primary_10_1039_D4NP00041B
crossref_primary_10_1007_s00253_015_7157_1
crossref_primary_10_1016_j_apsb_2022_09_008
crossref_primary_10_1080_14786419_2018_1493583
crossref_primary_10_3390_molecules23020299
crossref_primary_10_1021_jacs_6b12914
crossref_primary_10_1021_acschembio_2c00204
crossref_primary_10_3390_md16060177
crossref_primary_10_1073_pnas_1715954115
crossref_primary_10_1021_ja405518u
crossref_primary_10_1007_s00203_021_02548_4
crossref_primary_10_1039_D0NP00056F
crossref_primary_10_1021_acs_chemrev_6b00478
crossref_primary_10_1016_j_mec_2022_e00203
crossref_primary_10_3390_md17060339
crossref_primary_10_1039_C4NP00059E
crossref_primary_10_1007_s00253_016_7733_z
crossref_primary_10_1186_s40694_021_00120_9
crossref_primary_10_3389_fchem_2018_00314
crossref_primary_10_1016_j_cbpa_2015_11_001
crossref_primary_10_1039_C5SC01965F
crossref_primary_10_1021_acschembio_7b00814
crossref_primary_10_1016_j_copbio_2020_11_016
crossref_primary_10_1021_acs_orglett_0c02160
crossref_primary_10_1016_j_fgb_2016_01_014
crossref_primary_10_3389_fphar_2018_01355
crossref_primary_10_1039_C5SC01058F
crossref_primary_10_3390_ijms23073475
crossref_primary_10_1021_acs_orglett_5b03465
crossref_primary_10_1021_acs_orglett_8b00327
crossref_primary_10_1080_14786419_2018_1544977
crossref_primary_10_1016_j_procbio_2018_02_023
crossref_primary_10_1002_ange_202104014
crossref_primary_10_1021_jacs_5b00570
Cites_doi 10.1002/cbic.201200124
10.1039/c2np00084a
10.1016/j.tetlet.2006.06.086
10.2165/00003495-198800363-00015
10.1016/j.fgb.2004.08.001
10.1039/b820413f
10.1002/cbic.201200369
10.1128/AEM.00694-08
10.1039/C39810001042
10.1016/S0040-4020(01)83433-5
10.1248/cpb.31.1528
10.1021/ja1096682
10.1248/cpb.48.559
10.1074/jbc.M507528200
10.1016/j.fgb.2010.12.001
10.1038/nrmicro1286
10.1021/jo301592k
10.1039/c39820000781
10.1094/MPMI-23-4-0458
10.1021/np0501738
10.1021/ja209809t
10.1021/jo00394a023
ContentType Journal Article
Copyright Copyright © 2012 American Chemical Society
Copyright_xml – notice: Copyright © 2012 American Chemical Society
DBID AAYXX
CITATION
17B
1KM
BLEPL
DTL
EGQ
GKHJH
CGR
CUY
CVF
ECM
EIF
NPM
7X8
7S9
L.6
5PM
DOI 10.1021/ol302682z
DatabaseName CrossRef
Web of Knowledge
Index Chemicus
Web of Science Core Collection
Science Citation Index Expanded
Web of Science Primary (SCIE, SSCI & AHCI)
Web of Science - Science Citation Index Expanded - 2012
Medline
MEDLINE
MEDLINE (Ovid)
MEDLINE
MEDLINE
PubMed
MEDLINE - Academic
AGRICOLA
AGRICOLA - Academic
PubMed Central (Full Participant titles)
DatabaseTitle CrossRef
Web of Science
MEDLINE
Medline Complete
MEDLINE with Full Text
PubMed
MEDLINE (Ovid)
MEDLINE - Academic
AGRICOLA
AGRICOLA - Academic
DatabaseTitleList
MEDLINE - Academic
MEDLINE

AGRICOLA
Web of Science
Database_xml – sequence: 1
  dbid: NPM
  name: PubMed
  url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed
  sourceTypes: Index Database
– sequence: 2
  dbid: 1KM
  name: Index Chemicus
  url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC
  sourceTypes:
    Enrichment Source
    Index Database
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1523-7052
EndPage 5687
ExternalDocumentID PMC3538129
23116177
000311324100017
10_1021_ol302682z
b222073895
Genre Research Support, U.S. Gov't, Non-P.H.S
Journal Article
Research Support, N.I.H., Extramural
GrantInformation_xml – fundername: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Institute of General Medical Sciences (NIGMS)
  grantid: P01GM084077
– fundername: National Institute of General Medical Sciences; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Institute of General Medical Sciences (NIGMS)
  grantid: PO1GM084077
– fundername: Department of Energy, Office of the Biomass Program; United States Department of Energy (DOE)
– fundername: NIGMS NIH HHS
  grantid: P01GM084077
– fundername: NIGMS NIH HHS
  grantid: P01 GM084077
– fundername: National Institute of General Medical Sciences : NIGMS
  grantid: P01 GM084077 || GM
GroupedDBID -
.K2
123
4.4
53G
55A
5VS
7~N
AABXI
ABFLS
ABMVS
ABPTK
ABUCX
ACGFS
ACS
AEESW
AENEX
AFEFF
ALMA_UNASSIGNED_HOLDINGS
AQSVZ
BAANH
CS3
DU5
DZ
EBS
ED
ED~
F5P
GNL
IH9
IHE
JG
JG~
K2
LG6
P2P
RNS
ROL
TN5
UI2
VF5
VG9
W1F
X
YNT
---
-DZ
-~X
6P2
AAHBH
AAYXX
ABBLG
ABJNI
ABLBI
ABQRX
ADHLV
AHGAQ
CITATION
CUPRZ
GGK
17B
1KM
BLEPL
DTL
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
GROUPED_WOS_WEB_OF_SCIENCE
CGR
CUY
CVF
ECM
EIF
NPM
7X8
7S9
L.6
5PM
ID FETCH-LOGICAL-a496t-fd001a5f78d0a4051d0dfe583c419666cb8e82f075d8aeec66af74bd447244493
IEDL.DBID ACS
ISICitedReferencesCount 74
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000311324100017
ISSN 1523-7060
1523-7052
IngestDate Thu Aug 21 18:25:12 EDT 2025
Fri Jul 11 11:29:36 EDT 2025
Thu Jul 10 18:34:01 EDT 2025
Thu Jan 02 23:04:29 EST 2025
Wed Jul 09 08:21:29 EDT 2025
Fri Aug 29 16:01:37 EDT 2025
Tue Jul 01 03:07:40 EDT 2025
Thu Apr 24 23:03:29 EDT 2025
Thu Aug 27 13:42:00 EDT 2020
IsPeerReviewed true
IsScholarly true
Issue 22
Keywords ASPERGILLUS-TERREUS
3,5-DIMETHYLORSELLINATE
AUSTIN
METABOLITE
Language English
LinkModel DirectLink
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-a496t-fd001a5f78d0a4051d0dfe583c419666cb8e82f075d8aeec66af74bd447244493
Notes NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ORCID 0000-0002-3046-8240
0000-0002-6940-6696
PMID 23116177
PQID 1273246869
PQPubID 23479
PageCount 4
ParticipantIDs crossref_primary_10_1021_ol302682z
pubmedcentral_primary_oai_pubmedcentral_nih_gov_3538129
proquest_miscellaneous_2010197318
crossref_citationtrail_10_1021_ol302682z
proquest_miscellaneous_1273246869
acs_journals_10_1021_ol302682z
webofscience_primary_000311324100017
webofscience_primary_000311324100017CitationCount
pubmed_primary_23116177
ProviderPackageCode JG~
55A
AABXI
GNL
VF5
7~N
VG9
W1F
ACS
AEESW
AFEFF
.K2
ABMVS
ABUCX
IH9
BAANH
AQSVZ
ED~
UI2
CITATION
AAYXX
PublicationCentury 2000
PublicationDate 2012-11-16
PublicationDateYYYYMMDD 2012-11-16
PublicationDate_xml – month: 11
  year: 2012
  text: 2012-11-16
  day: 16
PublicationDecade 2010
PublicationPlace WASHINGTON
PublicationPlace_xml – name: WASHINGTON
– name: United States
PublicationTitle Organic letters
PublicationTitleAbbrev ORG LETT
PublicationTitleAlternate Org. Lett
PublicationYear 2012
Publisher American Chemical Society
Amer Chemical Soc
Publisher_xml – name: American Chemical Society
– name: Amer Chemical Soc
References Itoh T. (ref6/cit6) 2012; 13
Rank C. (ref13/cit13) 2006; 47
McIntyre C. R. (ref4/cit4) 1982
Sanchez J. F. (ref9/cit9) 2011; 133
McDonough M. A. (ref22/cit22) 2005; 280
ref16/cit16
Sanchez J. F. (ref15/cit15) 2012; 29
Chiang Y.-M. (ref18/cit18) 2011; 48
Springer J. P. (ref10/cit10) 1979; 44
McIntyre C. R. (ref5/cit5) 1989; 45
Rao K. V. (ref14/cit14) 2000; 48
Lo H.-C. (ref7/cit7) 2012; 134
Matsuda Y. (ref20/cit20) 2012; 13
Inderbitzin P. (ref8/cit8) 2010; 23
Li G.-Y. (ref11/cit11) 2005; 68
Keller N. P. (ref17/cit17) 2005; 3
Geris R. (ref2/cit2) 2009; 26
Simpson T. J. (ref3/cit3) 1981
Illingworth D. R. (ref1/cit1) 1988; 36
Yu J.-H. (ref19/cit19) 2004; 41
Bomke C. (ref21/cit21) 2008; 74
Nitta K. (ref12/cit12) 1983; 31
Rao, KV (WOS:000086300000021) 2000; 48
Yu, JH (WOS:000226263600001) 2004; 41
Inderbitzin, P (WOS:000275712000011) 2010; 23
MCINTYRE, CR (WOS:A1989U178100006) 1989; 45
MCINTYRE, CR (WOS:A1982NY37100006) 1982
Bomke, C (WOS:000258829100008) 2008; 74
Rank, C (WOS:000239885000021) 2006; 47
ILLINGWORTH, DR (WOS:A1988AK61400014) 1988; 36
Sanchez, JF (WOS:000300251800002) 2012; 29
Matsuda, Y (WOS:000307102000006) 2012; 13
SIMPSON, TJ (WOS:A1981ML69100015) 1981
Sanchez, JF (WOS:000288889900060) 2011; 133
McDonough, MA (WOS:000233666600084) 2005; 280
Keller, NP (WOS:000233668900013) 2005; 3
Chiang, YM (WOS:000288590300010) 2011; 48
Lo, HC (WOS:000301990600047) 2012; 134
Chooi, YH (WOS:000311073000001) 2012; 77
Itoh, T (WOS:000304346600010) 2012; 13
SPRINGER, JP (WOS:A1979HY82300023) 1979; 44
Geris, R (WOS:000268370800005) 2009; 26
Li, GY (WOS:000231578000020) 2005; 68
NITTA, K (WOS:A1983QZ61800010) 1983; 31
References_xml – volume: 13
  start-page: 1132
  year: 2012
  ident: ref6/cit6
  publication-title: ChemBioChem
  doi: 10.1002/cbic.201200124
– volume: 29
  start-page: 351
  year: 2012
  ident: ref15/cit15
  publication-title: Nat. Prod. Rep.
  doi: 10.1039/c2np00084a
– volume: 47
  start-page: 6099
  year: 2006
  ident: ref13/cit13
  publication-title: Tetrahedron Lett.
  doi: 10.1016/j.tetlet.2006.06.086
– volume: 36
  start-page: 63
  issue: 3
  year: 1988
  ident: ref1/cit1
  publication-title: Drugs
  doi: 10.2165/00003495-198800363-00015
– volume: 41
  start-page: 973
  year: 2004
  ident: ref19/cit19
  publication-title: Fungal Genet. Biol.
  doi: 10.1016/j.fgb.2004.08.001
– volume: 26
  start-page: 1063
  year: 2009
  ident: ref2/cit2
  publication-title: Nat. Prod. Rep.
  doi: 10.1039/b820413f
– volume: 13
  start-page: 1738
  year: 2012
  ident: ref20/cit20
  publication-title: ChemBioChem
  doi: 10.1002/cbic.201200369
– volume: 74
  start-page: 5325
  year: 2008
  ident: ref21/cit21
  publication-title: Appl. Environ. Microbiol.
  doi: 10.1128/AEM.00694-08
– start-page: 1042
  year: 1981
  ident: ref3/cit3
  publication-title: J. Chem. Soc., Chem. Commun.
  doi: 10.1039/C39810001042
– volume: 45
  start-page: 2307
  year: 1989
  ident: ref5/cit5
  publication-title: Tetrahedron
  doi: 10.1016/S0040-4020(01)83433-5
– volume: 31
  start-page: 1528
  year: 1983
  ident: ref12/cit12
  publication-title: Chem. Pharm. Bull.
  doi: 10.1248/cpb.31.1528
– volume: 133
  start-page: 4010
  year: 2011
  ident: ref9/cit9
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja1096682
– volume: 48
  start-page: 559
  year: 2000
  ident: ref14/cit14
  publication-title: Chem. Pharm. Bull.
  doi: 10.1248/cpb.48.559
– volume: 280
  start-page: 41101
  year: 2005
  ident: ref22/cit22
  publication-title: J. Biol. Chem.
  doi: 10.1074/jbc.M507528200
– volume: 48
  start-page: 430
  year: 2011
  ident: ref18/cit18
  publication-title: Fungal Genet. Biol.
  doi: 10.1016/j.fgb.2010.12.001
– volume: 3
  start-page: 937
  year: 2005
  ident: ref17/cit17
  publication-title: Nat. Rev. Microbiol.
  doi: 10.1038/nrmicro1286
– ident: ref16/cit16
  doi: 10.1021/jo301592k
– start-page: 781
  year: 1982
  ident: ref4/cit4
  publication-title: J. Chem. Soc., Chem. Commun.
  doi: 10.1039/c39820000781
– volume: 23
  start-page: 458
  year: 2010
  ident: ref8/cit8
  publication-title: Mol. Plant-Microbe Interact.
  doi: 10.1094/MPMI-23-4-0458
– volume: 68
  start-page: 1243
  year: 2005
  ident: ref11/cit11
  publication-title: J. Nat. Prod.
  doi: 10.1021/np0501738
– volume: 134
  start-page: 4709
  year: 2012
  ident: ref7/cit7
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja209809t
– volume: 44
  start-page: 4852
  year: 1979
  ident: ref10/cit10
  publication-title: J. Org. Chem.
  doi: 10.1021/jo00394a023
– volume: 13
  start-page: 1738
  year: 2012
  ident: WOS:000307102000006
  article-title: Terretonin Biosynthesis Requires Methylation as Essential Step for Cyclization
  publication-title: CHEMBIOCHEM
  doi: 10.1002/cbic.201200369
– volume: 44
  start-page: 4852
  year: 1979
  ident: WOS:A1979HY82300023
  article-title: TERRETONIN, A TOXIC COMPOUND FROM ASPERGILLUS-TERREUS
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
– volume: 13
  start-page: 1132
  year: 2012
  ident: WOS:000304346600010
  article-title: Identification of a Key Prenyltransferase Involved in Biosynthesis of the Most Abundant Fungal Meroterpenoids Derived from 3,5-Dimethylorsellinic Acid.
  publication-title: CHEMBIOCHEM
  doi: 10.1002/cbic.201200124
– volume: 133
  start-page: 4010
  year: 2011
  ident: WOS:000288889900060
  article-title: Genome-Based Deletion Analysis Reveals the Prenyl Xanthone Biosynthesis Pathway in Aspergillus nidulans
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja1096682
– volume: 48
  start-page: 559
  year: 2000
  ident: WOS:000086300000021
  article-title: Butyrolactones from Aspergillus terreus
  publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN
– volume: 41
  start-page: 973
  year: 2004
  ident: WOS:000226263600001
  article-title: Double-joint PCR: a PCR-based molecular tool for gene manipulations in filamentous fungi
  publication-title: FUNGAL GENETICS AND BIOLOGY
  doi: 10.1016/j.fgb.2004.08.001
– volume: 36
  start-page: 63
  year: 1988
  ident: WOS:A1988AK61400014
  article-title: AN OVERVIEW OF LIPID-LOWERING DRUGS
  publication-title: DRUGS
– volume: 3
  start-page: 937
  year: 2005
  ident: WOS:000233668900013
  article-title: Fungal secondary metabolism - From biochemistry to genomics
  publication-title: NATURE REVIEWS MICROBIOLOGY
  doi: 10.1038/nrmicro1286
– volume: 134
  start-page: 4709
  year: 2012
  ident: WOS:000301990600047
  article-title: Two Separate Gene Clusters Encode the Biosynthetic Pathway for the Meroterpenoids Austinol and Dehydroaustinol in Aspergillus nidulans
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja209809t
– volume: 74
  start-page: 5325
  year: 2008
  ident: WOS:000258829100008
  article-title: Isolation and characterization of the gibberellin biosynthetic gene cluster in Sphaceloma manihoticola
  publication-title: APPLIED AND ENVIRONMENTAL MICROBIOLOGY
  doi: 10.1128/AEM.00694-08
– start-page: 1042
  year: 1981
  ident: WOS:A1981ML69100015
  article-title: BIOSYNTHESIS OF AUSTIN, A POLYKETIDE-TERPENOID METABOLITE OF ASPERGILLUS-USTUS
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS
– volume: 77
  start-page: 9933
  year: 2012
  ident: WOS:000311073000001
  article-title: Navigating the Fungal Polyketide Chemical Space: From Genes to Molecules
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo301592k
– volume: 45
  start-page: 2307
  year: 1989
  ident: WOS:A1989U178100006
  article-title: APPLICATION OF STABLE ISOTOPE LABELING METHODOLOGY TO THE BIOSYNTHESIS OF THE MYCOTOXIN, TERRETONIN, BY ASPERGILLUS-TERREUS - INCORPORATION OF C-13-LABELED ACETATES AND METHIONINE, H-2-LABELED AND C-13-LABELED, O-18-LABELED ETHYL 3,5-DIMETHYLORSELLINATE AND O-18 GAS
  publication-title: TETRAHEDRON
– volume: 68
  start-page: 1243
  year: 2005
  ident: WOS:000231578000020
  article-title: Sesterterpenoids, terretonins A-D, and an alkaloid, asterrelenin, from Aspergallus terreus
  publication-title: JOURNAL OF NATURAL PRODUCTS
  doi: 10.1021/np0501738
– volume: 47
  start-page: 6099
  year: 2006
  ident: WOS:000239885000021
  article-title: epi-Aszonalenins A, B, and C from Aspergillus novofumigatus
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/j.tetlet.2006.06.086
– start-page: 781
  year: 1982
  ident: WOS:A1982NY37100006
  article-title: BIOSYNTHESIS OF THE MEROTERPENOID METABOLITES, AUSTIN AND TERRETONIN - INCORPORATION OF 3,5-DIMETHYLORSELLINATE
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS
– volume: 280
  start-page: 41101
  year: 2005
  ident: WOS:000233666600084
  article-title: Structure of human phytanoyl-CoA 2-hydroxylase identifies molecular mechanisms of Refsum disease
  publication-title: JOURNAL OF BIOLOGICAL CHEMISTRY
  doi: 10.1074/jbc.M507528200
– volume: 26
  start-page: 1063
  year: 2009
  ident: WOS:000268370800005
  article-title: Meroterpenoids produced by fungi
  publication-title: NATURAL PRODUCT REPORTS
  doi: 10.1039/b820413f
– volume: 31
  start-page: 1528
  year: 1983
  ident: WOS:A1983QZ61800010
  article-title: METABOLIC PRODUCTS OF ASPERGILLUS-TERREUS .9. BIOSYNTHESIS OF BUTYROLACTONE DERIVATIVES ISOLATED FROM STRAINS-IFO-8835 AND STRAIN-IFO-4100
  publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN
– volume: 48
  start-page: 430
  year: 2011
  ident: WOS:000288590300010
  article-title: Characterization of a polyketide synthase in Aspergillus niger whose product is a precursor for both dihydroxynaphthalene (DHN) melanin and naphtho-gamma-pyrone
  publication-title: FUNGAL GENETICS AND BIOLOGY
  doi: 10.1016/j.fgb.2010.12.001
– volume: 29
  start-page: 351
  year: 2012
  ident: WOS:000300251800002
  article-title: Advances in Aspergillus secondary metabolite research in the post-genomic era
  publication-title: NATURAL PRODUCT REPORTS
  doi: 10.1039/c2np00084a
– volume: 23
  start-page: 458
  year: 2010
  ident: WOS:000275712000011
  article-title: Six New Genes Required for Production of T-Toxin, a Polyketide Determinant of High Virulence of Cochliobolus heterostrophus to Maize
  publication-title: MOLECULAR PLANT-MICROBE INTERACTIONS
  doi: 10.1094/MPMI-23-4-0458
SSID ssj0011529
Score 2.3570921
Snippet Meroterpenoids are natural products produced from polyketide and terpenoid precursors. A gene targeting system for A. terreus NIH2624 was developed, and a gene...
Meroterpenoids are natural products produced from polyketide and terpenoid precursors. A gene targeting system for A. terreus NIH2624 was developed and a gene...
Source Web of Science
SourceID pubmedcentral
proquest
pubmed
webofscience
crossref
acs
SourceType Open Access Repository
Aggregation Database
Index Database
Enrichment Source
Publisher
StartPage 5684
SubjectTerms Aspergillus nidulans - chemistry
Aspergillus nidulans - genetics
Aspergillus nidulans - metabolism
biosynthesis
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
gene targeting
Molecular Structure
multigene family
mutants
Physical Sciences
polyketides
Science & Technology
Terpenes - chemistry
terpenoids
Title Molecular Genetic Characterization of a Cluster in A. terreus for Biosynthesis of the Meroterpenoid Terretonin
URI http://dx.doi.org/10.1021/ol302682z
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000311324100017
https://www.ncbi.nlm.nih.gov/pubmed/23116177
https://www.proquest.com/docview/1273246869
https://www.proquest.com/docview/2010197318
https://pubmed.ncbi.nlm.nih.gov/PMC3538129
Volume 14
WOS 000311324100017
WOSCitedRecordID wos000311324100017
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1Lb9QwEB6VcoBLeUN4VAZ64JIlD6-THJdAVSEtF1qpt8hPdcUqqTbJof31zOSlLt0Cp0TKl8SejDXfxPY3AEeZEtIoGfiGC-HzKDC-TLTzA-VUhg6jdEwbnJc_xMkZ_34-P9-Dj3fM4Efh52odY56QRtf34D4eE8qwFvnPaaoAA1DWiaJGsU9SMKN80M1bKfToejv03OKTu5dF_hGKurBz_Ai-jpt3-tUmv2Zto2b6-raW49969BgOBtrJFr2fPIE9Wz6FB_lY7e0ZlMuxTi4jJWqEsXzScu63arLKMcnydUvaCmxVssWM4dnGtjVD6su-rKr6qkRCWa9qwuIZW1rSgdhc2rJaGXZK6IZ-AD-Hs-Nvp_mJP9Ri8CXPROM7g6aWc5ekJpBI8kITGGfnaaw5jmEhtEptGjkkICaV1mohpEu4MpwnSCB4Fr-A_bIq7StgCh-BREhzTTWStFXSJip2yVwal2Yq9eAQP1YxjKW66KbJo7CYzObBp_E7FnpQMqeCGutd0A8T9LKX79gFej86Q4FWpxkTWdqqxVcjuYu4SEV2N4aWE4RUAAwb_rJ3oOlVSJ4pf0w8SLZcawKQuPf2lXJ10Yl8xxiJkIt5cHTTCacbKZcNQ2xc2EkeeRD-DywfrEV6B83rf9n5DTzEzkW08zIUb2G_2bT2HVKwRh12Q_A3KGEtdA
linkProvider American Chemical Society
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwzV1Lb9QwELaqcigX3o-0UAwqEpds8_A6yYHDEqi2tNsLW6m34KdYsUqqTSLU_hT-Cn-OmWwSumURXCpxi5SJ44zHnm_i8TeE7CWSCy2F52rGucsCT7siUtb1pJUJGIxUIR5wnpzw8Sn7eDY82yDfu7Mw0IkSWiqbTfxf7AL-fjEPIVyIg8s2gfLIXHyD8Kx8e_gexvJ1EBx8mKZjt60g4AqW8Mq1GlZhMbRRrD0B0MTXnrZmGIeKgeVxrmRs4sCC29SxMEZxLmzEpGYsArfHkGgJlvdbAHoCDOxG6ad-hwL8XtJwsQahiww0HWvR1a6ix1Plqsf7Dcauz8a85gEbb3dwl_zo9dQkuXwd1JUcqMtrFJL_pyLvkTstyKaj5ay4TzZM_oBspV1tu4ckn3RVgSnyboMYTXvm6uXBVFpYKmg6r5FJgs5yOhpQuFqYuqQA9Om7WVFe5ACfy1mJsnBFJwZZLxbnJi9mmk5RusLf3Y_I6Y187mOymRe5eUqohCYA9immsCKUMlKYSIY2Ggpt40TGDtmFUcralaPMmqSAwM_6YXLIm858MtXytmP5kPk60Ve96PmSrGSd0MvOBjPQOu4PidwUNbwaoGzAeMyTP8tg8oSP5c6g40-Wdtu_CkIFjJYjh0QrFt0LIJX56p189qWhNA_B7wLydMjeVdvvH8TI3fehc35D8OQQ_1_E0lZbyO5Qbf9Nzy_I1ng6Oc6OD0-Odsht-NAAz5z6_BnZrBa1eQ7gs5K7zSpAyeebni0_AUF0j90
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwzV1Lb9QwELaqIgGX8obwKAYViUuWPLxOcuCwpKxaylZItFJvqZ9i1VWy2iRC7Y_hr_DXmMkmUbcsgkslbpHyJbHHY89MPP6GkJ1EcqGl8FzNOHdZ4GlXRMq6nrQyAYWRKsQDzpNDvnfMPp0MTzbIj-4sDDSihDeVzSY-zuq5ti3DgP-umIUQMsTBRZtEeWDOv0OIVr7f34XxfBME449H6Z7bVhFwBUt45VoNK7EY2ijWngD3xNeetmYYh4qB9nGuZGziwILp1LEwRnEubMSkZiwC08eQbAmW-Bu4PYjB3Sj92u9SgO1LGj7WIHSRhaZjLrrcVLR6qly1er-5suszMq9Ywcbije-Qn72smkSXs0FdyYG6uEIj-f8K8y7Zap1tOlrOjntkw-T3ya20q3H3gOSTrjowRf5tgNG0Z7BeHlClhaWCprMaGSXoNKejAYWrhalLCg4__TAtyvMc3OhyWiIWrujEIPvFYm7yYqrpEaIr_O39kBxfS3cfkc28yM0TQiW8Atw_xRRWhlJGChPJ0EZDoW2cyNgh2zBSWbuClFmTHBD4WT9MDnnbqVCmWv52LCMyWwd93UPnS9KSdaBXnR5mIHXcJxK5KWr4NLi0AeMxT_6MwSQKH8ueQcMfL3W3_xSEDBg1Rw6JVrS6ByCl-eqdfPqtoTYPwf6CB-qQncv63z-IEbzvQ-P8hujJIf6_wNJWWsjyUD39m5xfkptfdsfZ5_3Dg2fkNvQzwKOnPn9ONqtFbV6AD1rJ7WYhoOT0uifLLzxOkmA
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Molecular+genetic+characterization+of+a+cluster+in+A.+terreus+for+biosynthesis+of+the+meroterpenoid+terretonin&rft.jtitle=Organic+letters&rft.au=Guo%2C+Chun-Jun&rft.au=Knox%2C+Benjamin+P.&rft.au=Chiang%2C+Yi-Ming&rft.au=Lo%2C+Hsien-Chun&rft.date=2012-11-16&rft.issn=1523-7060&rft.eissn=1523-7052&rft.volume=14&rft.issue=22&rft.spage=5684&rft.epage=5687&rft_id=info:doi/10.1021%2Fol302682z&rft_id=info%3Apmid%2F23116177&rft.externalDocID=PMC3538129
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1523-7060&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1523-7060&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1523-7060&client=summon