Rational Domain Swaps Decipher Programming in Fungal Highly Reducing Polyketide Synthases and Resurrect an Extinct Metabolite

The mechanism of programming of iterative highly reducing polyketide synthases remains one of the key unsolved problems of secondary metabolism. We conducted rational domain swaps between the polyketide synthases encoding the biosynthesis of the closely related compounds tenellin and desmethylbassia...

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Published inJournal of the American Chemical Society Vol. 133; no. 41; pp. 16635 - 16641
Main Authors Fisch, Katja M, Bakeer, Walid, Yakasai, Ahmed A, Song, Zhongshu, Pedrick, Jennifer, Wasil, Zahida, Bailey, Andrew M, Lazarus, Colin M, Simpson, Thomas J, Cox, Russell J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.10.2011
Amer Chemical Soc
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Abstract The mechanism of programming of iterative highly reducing polyketide synthases remains one of the key unsolved problems of secondary metabolism. We conducted rational domain swaps between the polyketide synthases encoding the biosynthesis of the closely related compounds tenellin and desmethylbassianin. Expression of the hybrid synthetases in Aspergillus oryzae led to the production of reprogrammed compounds in which the changes to the methylation pattern and chain length could be mapped to the domain swaps. These experiments reveal for the first time the origin of programming in these systems. Domain swaps combined with coexpression of two cytochrome P450 encoding genes from the tenellin biosynthetic gene cluster led to the resurrection of the extinct metabolite bassianin.
AbstractList The mechanism of programming of iterative highly reducing polyketide synthases remains one of the key unsolved problems of secondary metabolism. We conducted rational domain swaps between the polyketide synthases encoding the biosynthesis of the closely related compounds tenellin and desmethylbassianin. Expression of the hybrid synthetases in Aspergillus oryzae led to the production of reprogrammed compounds in which the changes to the methylation pattern and chain length could be mapped to the domain swaps. These experiments reveal for the first time the origin of programming in these systems. Domain swaps combined with coexpression of two cytochrome P450 encoding genes from the tenellin biosynthetic gene cluster led to the resurrection of the extinct metabolite bassianin.
Author Bakeer, Walid
Cox, Russell J
Fisch, Katja M
Lazarus, Colin M
Song, Zhongshu
Pedrick, Jennifer
Bailey, Andrew M
Simpson, Thomas J
Wasil, Zahida
Yakasai, Ahmed A
AuthorAffiliation University of Bristol
Beni Suef University
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  givenname: Katja M
  surname: Fisch
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  surname: Song
  fullname: Song, Zhongshu
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  givenname: Jennifer
  surname: Pedrick
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  givenname: Zahida
  surname: Wasil
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  surname: Bailey
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  surname: Cox
  fullname: Cox, Russell J
  email: r.j.cox@bris.ac.uk, tom.simpson@bris.ac.uk
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Cites_doi 10.1039/c0cc01162b
10.1021/bi701784c
10.1039/a909079g
10.1126/science.1175602
10.1021/ja107084d
10.1039/b923990a
10.1039/b704420h
10.1021/ja803078z
10.1021/ja0672122
10.1107/S1744309107047069
10.1038/nsmb808
10.1126/science.1161269
10.1021/ja0317271
10.1039/b912037h
10.1039/c1sc00023c
10.1038/nature08475
10.1002/cbic.200600398
10.1039/b708614h
10.1002/anie.201007671
10.1126/science.1154711
10.1021/ja807052c
10.1002/cbic.201000259
10.1007/s10295-006-0137-9
10.1021/bi901123r
10.1073/pnas.0604112103
10.1002/cbic.200700390
10.1126/science.284.5418.1368
10.1039/c39740000282
10.1042/bj2880839
10.1016/S1074-5521(96)90069-1
10.1139/v77-580
10.1039/B912037H
10.1073/pnas.0406901101
10.1016/S0040-4020(98)00557-2
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Issue 41
Keywords KETOSYNTHASE DOMAIN
2-PYRIDONE TENELLIN
FATTY-ACID SYNTHASE
BEAUVERIA-BASSIANA
PROTEINS
BIOSYNTHESIS
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References Liu, XY (WOS:000269485500028) 2009; 48
Kennedy, J (WOS:000080430600057) 1999; 284
Du, LC (WOS:000274073100004) 2010; 27
SPENCER, JB (WOS:A1992KE17900022) 1992; 288
Heneghan, MN (WOS:000290629600021) 2011; 2
Zha, WJ (WOS:000220752300037) 2004; 126
Staunton, J (WOS:000170086100002) 2001; 18
MCINNES, AG (WOS:A1974S678200002) 1974
Jessen, HJ (WOS:000290662500036) 2011; 50
Xu, W (WOS:000282864100014) 2010; 132
Chakravarty, B (WOS:000224922300006) 2004; 101
Ma, SM (WOS:000271019400046) 2009; 326
Zhu, X (WOS:000240473100007) 2006; 33
Fisch, KM (WOS:000279911000038) 2010; 46
Morita, H (WOS:000251799400011) 2007; 63
Sims, JW (WOS:000258415900060) 2008; 130
Halo, LM (WOS:000253800300015) 2008; 9
Zhu, XC (WOS:000243195100018) 2007; 129
Crawford, JM (WOS:000241969500021) 2006; 103
Crawford, JM (WOS:000270987600048) 2009; 461
Beltran-Alvarez, P (WOS:000251547700033) 2007; 46
Crawford, JM (WOS:000254836700047) 2008; 320
Oliynyk, M (WOS:A1996VR14500007) 1996; 3
WAT, CK (WOS:A1977EH20700020) 1977; 55
Eley, KL (WOS:000244440100005) 2007; 8
Bailey, AM (WOS:000249925400031) 2007
Skellam, EJ (WOS:000275715000008) 2010; 6
Maier, T (WOS:000258914300040) 2008; 321
Heneghan, MN (WOS:000281383200005) 2010; 11
Moore, MC (WOS:000074744700026) 1998; 54
Halo, LM (WOS:000263320900057) 2008; 130
Cox, RJ (WOS:000247397900013) 2007; 5
Keatinge-Clay, A (WOS:000223540200024) 2004; 11
Chakravarty B. (ref24/cit24) 2004; 101
Fisch K. M. (ref25/cit25) 2010; 46
Staunton J. (ref2/cit2) 2001; 18
Crawford J. M. (ref3/cit3) 2006; 103
Halo L. M. (ref14/cit14) 2008; 9
Heneghan M. N. (ref7/cit7) 2011; 2
Halo L. M. (ref15/cit15) 2008; 130
Bailey A. M. (ref26/cit26) 2007
Beltran-Alvarez P. (ref33/cit33) 2007; 46
Zha W. (ref28/cit28) 2004; 126
Kennedy J. (ref17/cit17) 1999; 284
Keatinge-Clay A. T. (ref20/cit20) 2004; 11
Moore M. (ref13/cit13) 1998; 54
Maier T. (ref16/cit16) 2008; 321
Keatinge-Clay A. T. (ref34/cit34) 2004; 11
McInnes A. (ref6/cit6) 1974
Jessen H. J. (ref8/cit8) 2011; 50
Eley K. L. (ref9/cit9) 2007; 8
Du L. (ref12/cit12) 2010; 27
Heneghan M. N. (ref19/cit19) 2010; 11
Sims J. W. (ref10/cit10) 2008; 130
Crawford J. M. (ref5/cit5) 2008; 320
Zhu X. (ref23/cit23) 2007; 129
Cox R. J. (ref1/cit1) 2007; 5
Wat C.-K. (ref31/cit31) 1977; 55
Spencer J. (ref29/cit29) 1992; 288
Skellam E. J. (ref27/cit27) 2010; 6
Zhu X. (ref22/cit22) 2006; 33
Crawford J. M. (ref4/cit4) 2009; 461
Oliynyk M. (ref18/cit18) 1996; 3
Xu W. (ref30/cit30) 2010; 132
Morita H. (ref21/cit21) 2007; 63
Liu X. (ref11/cit11) 2009; 48
Ma S. M. (ref32/cit32) 2009; 326
References_xml – volume: 46
  start-page: 5331
  year: 2010
  ident: WOS:000279911000038
  article-title: Catalytic role of the C-terminal domains of a fungal non-reducing polyketide synthase
  publication-title: CHEMICAL COMMUNICATIONS
  doi: 10.1039/c0cc01162b
  contributor:
    fullname: Fisch, KM
– volume: 46
  start-page: 14672
  year: 2007
  ident: WOS:000251547700033
  article-title: Dissecting the component reactions catalyzed by the actinorhodin minimal polyketide synthase
  publication-title: BIOCHEMISTRY
  doi: 10.1021/bi701784c
  contributor:
    fullname: Beltran-Alvarez, P
– volume: 18
  start-page: 380
  year: 2001
  ident: WOS:000170086100002
  article-title: Polyketide biosynthesis: a millennium review
  publication-title: NATURAL PRODUCT REPORTS
  doi: 10.1039/a909079g
  contributor:
    fullname: Staunton, J
– volume: 326
  start-page: 589
  year: 2009
  ident: WOS:000271019400046
  article-title: Complete Reconstitution of a Highly Reducing Iterative Polyketide Synthase
  publication-title: SCIENCE
  doi: 10.1126/science.1175602
  contributor:
    fullname: Ma, SM
– volume: 132
  start-page: 13604
  year: 2010
  ident: WOS:000282864100014
  article-title: Analysis of Intact and Dissected Fungal Polyketide Synthase-Nonribosomal Peptide Synthetase in Vitro and in Saccharomyces cerevisiae
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja107084d
  contributor:
    fullname: Xu, W
– volume: 6
  start-page: 680
  year: 2010
  ident: WOS:000275715000008
  article-title: Mutation of key residues in the C-methyltransferase domain of a fungal highly reducing polyketide synthase
  publication-title: MOLECULAR BIOSYSTEMS
  doi: 10.1039/b923990a
  contributor:
    fullname: Skellam, EJ
– volume: 5
  start-page: 2010
  year: 2007
  ident: WOS:000247397900013
  article-title: Polyketides, proteins and genes in fungi: programmed nano-machines begin to reveal their secrets
  publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY
  doi: 10.1039/b704420h
  contributor:
    fullname: Cox, RJ
– volume: 288
  start-page: 839
  year: 1992
  ident: WOS:A1992KE17900022
  article-title: PURIFICATION AND PROPERTIES OF 6-METHYLSALICYLIC ACID SYNTHASE FROM PENICILLIUM-PATULUM
  publication-title: BIOCHEMICAL JOURNAL
  contributor:
    fullname: SPENCER, JB
– volume: 130
  start-page: 11149
  year: 2008
  ident: WOS:000258415900060
  article-title: Thioesterase-like role for fungal PKS-NRPS hybrid reductive domains
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja803078z
  contributor:
    fullname: Sims, JW
– volume: 129
  start-page: 36
  year: 2007
  ident: WOS:000243195100018
  article-title: Production of dihydroisocoumarins in Fusarium verticillioides by swapping ketosynthase domain of the fungal iterative polyketide synthase Fum1p with that of lovastatin diketide synthase
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja0672122
  contributor:
    fullname: Zhu, XC
– volume: 63
  start-page: 947
  year: 2007
  ident: WOS:000251799400011
  article-title: Crystallization and preliminary crystallographic analysis of an octaketide-producing plant type III polyketide synthase
  publication-title: ACTA CRYSTALLOGRAPHICA SECTION F-STRUCTURAL BIOLOGY COMMUNICATIONS
  doi: 10.1107/S1744309107047069
  contributor:
    fullname: Morita, H
– volume: 11
  start-page: 888
  year: 2004
  ident: WOS:000223540200024
  article-title: An antibiotic factory caught in action
  publication-title: NATURE STRUCTURAL & MOLECULAR BIOLOGY
  doi: 10.1038/nsmb808
  contributor:
    fullname: Keatinge-Clay, A
– volume: 284
  start-page: 1368
  year: 1999
  ident: WOS:000080430600057
  article-title: Modulation of polyketide synthase activity by accessory proteins during lovastatin biosynthesis
  publication-title: SCIENCE
  contributor:
    fullname: Kennedy, J
– start-page: 282
  year: 1974
  ident: WOS:A1974S678200002
  article-title: NEW TECHNIQUES IN BIOSYNTHETIC STUDIES USING C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY - BIOSYNTHESIS OF TENELLIN ENRICHED FROM SINGLY AND DOUBLY LABELED PRECURSORS
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS
  contributor:
    fullname: MCINNES, AG
– volume: 321
  start-page: 1315
  year: 2008
  ident: WOS:000258914300040
  article-title: The crystal structure of a mammalian fatty acid synthase
  publication-title: SCIENCE
  doi: 10.1126/science.1161269
  contributor:
    fullname: Maier, T
– volume: 126
  start-page: 4534
  year: 2004
  ident: WOS:000220752300037
  article-title: Rational pathway engineering of type I fatty acid synthase allows the biosynthesis of triacetic acid lactone from D-glucose in vivo
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja0317271
  contributor:
    fullname: Zha, WJ
– volume: 27
  start-page: 255
  year: 2010
  ident: WOS:000274073100004
  article-title: PKS and NRPS release mechanisms
  publication-title: NATURAL PRODUCT REPORTS
  doi: 10.1039/b912037h
  contributor:
    fullname: Du, LC
– volume: 2
  start-page: 972
  year: 2011
  ident: WOS:000290629600021
  article-title: The programming role of trans-acting enoyl reductases during the biosynthesis of highly reduced fungal polyketides
  publication-title: CHEMICAL SCIENCE
  doi: 10.1039/c1sc00023c
  contributor:
    fullname: Heneghan, MN
– volume: 461
  start-page: 1139
  year: 2009
  ident: WOS:000270987600048
  article-title: Structural basis for biosynthetic programming of fungal aromatic polyketide cyclization
  publication-title: NATURE
  doi: 10.1038/nature08475
  contributor:
    fullname: Crawford, JM
– volume: 8
  start-page: 289
  year: 2007
  ident: WOS:000244440100005
  article-title: Biosynthesis of the 2-pyridone tenellin in the insect pathogenic fungus Beauveria bassiana
  publication-title: CHEMBIOCHEM
  doi: 10.1002/cbic.200600398
  contributor:
    fullname: Eley, KL
– start-page: 4053
  year: 2007
  ident: WOS:000249925400031
  article-title: Characterisation of 3-methylorcinaldehyde synthase (MOS) in Acremonium strictum: first observation of a reductive release mechanism during polyketide biosynthesis
  publication-title: CHEMICAL COMMUNICATIONS
  doi: 10.1039/b708614h
  contributor:
    fullname: Bailey, AM
– volume: 50
  start-page: 4222
  year: 2011
  ident: WOS:000290662500036
  article-title: A Unified Approach for the Stereoselective Total Synthesis of Pyridone Alkaloids and Their Neuritogenic Activity
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201007671
  contributor:
    fullname: Jessen, HJ
– volume: 320
  start-page: 243
  year: 2008
  ident: WOS:000254836700047
  article-title: Deconstruction of iterative multidomain polyketide synthase function
  publication-title: SCIENCE
  doi: 10.1126/science.1154711
  contributor:
    fullname: Crawford, JM
– volume: 130
  start-page: 17988
  year: 2008
  ident: WOS:000263320900057
  article-title: Late Stage Oxidations during the Biosynthesis of the 2-Pyridone Tenellin in the Entomopathogenic Fungus Beauveria bassiana
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja807052c
  contributor:
    fullname: Halo, LM
– volume: 3
  start-page: 833
  year: 1996
  ident: WOS:A1996VR14500007
  article-title: A hybrid modular polyketide synthase obtained by domain swapping
  publication-title: CHEMISTRY & BIOLOGY
  contributor:
    fullname: Oliynyk, M
– volume: 101
  start-page: 15567
  year: 2004
  ident: WOS:000224922300006
  article-title: Human fatty acid synthase: Structure and substrate selectivity of the thioesterase domain
  publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
  contributor:
    fullname: Chakravarty, B
– volume: 11
  start-page: 1508
  year: 2010
  ident: WOS:000281383200005
  article-title: First Heterologous Reconstruction of a Complete Functional Fungal Biosynthetic Multigene Cluster
  publication-title: CHEMBIOCHEM
  doi: 10.1002/cbic.201000259
  contributor:
    fullname: Heneghan, MN
– volume: 54
  start-page: 9195
  year: 1998
  ident: WOS:000074744700026
  article-title: Synthesis and evaluation of a putative acyl tetramic acid intermediate in tenellin biosynthesis in Beauveria bassiana. A new role for tyrosine
  publication-title: TETRAHEDRON
  contributor:
    fullname: Moore, MC
– volume: 33
  start-page: 859
  year: 2006
  ident: WOS:000240473100007
  article-title: Functional replacement of the ketosynthase domain of FUM1 for the biosynthesis of fumonisins, a group of fungal reduced polyketides
  publication-title: JOURNAL OF INDUSTRIAL MICROBIOLOGY & BIOTECHNOLOGY
  doi: 10.1007/s10295-006-0137-9
  contributor:
    fullname: Zhu, X
– volume: 48
  start-page: 8746
  year: 2009
  ident: WOS:000269485500028
  article-title: Cyclopiazonic Acid Biosynthesis in Aspergillus sp.: Characterization of a Reductase-like R* Domain in Cyclopiazonate Synthetase That Forms and Releases cyclo-Acetoacetyl-L-tryptophan
  publication-title: BIOCHEMISTRY
  doi: 10.1021/bi901123r
  contributor:
    fullname: Liu, XY
– volume: 55
  start-page: 4090
  year: 1977
  ident: WOS:A1977EH20700020
  article-title: YELLOW PIGMENTS OF BEAUVERIA SPECIES - STRUCTURES OF TENELLIN AND BASSIANIN
  publication-title: CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
  contributor:
    fullname: WAT, CK
– volume: 103
  start-page: 16728
  year: 2006
  ident: WOS:000241969500021
  article-title: Identification of a starter unit acyl-carrier protein transacylase domain in an iterative type I polyketide synthase
  publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
  doi: 10.1073/pnas.0604112103
  contributor:
    fullname: Crawford, JM
– volume: 9
  start-page: 585
  year: 2008
  ident: WOS:000253800300015
  article-title: Authentic heterologous expression of the tenellin iterative polyketide synthase nonribosomal peptide synthetase requires coexpression with an enoyl reductase
  publication-title: CHEMBIOCHEM
  doi: 10.1002/cbic.200700390
  contributor:
    fullname: Halo, LM
– volume: 5
  start-page: 2010
  year: 2007
  ident: ref1/cit1
  publication-title: Org. Biomol. Chem.
  doi: 10.1039/b704420h
  contributor:
    fullname: Cox R. J.
– volume: 284
  start-page: 1368
  year: 1999
  ident: ref17/cit17
  publication-title: Science
  doi: 10.1126/science.284.5418.1368
  contributor:
    fullname: Kennedy J.
– volume: 46
  start-page: 14672
  year: 2007
  ident: ref33/cit33
  publication-title: Biochemistry
  doi: 10.1021/bi701784c
  contributor:
    fullname: Beltran-Alvarez P.
– volume: 11
  start-page: 888
  year: 2004
  ident: ref20/cit20
  publication-title: Nat. Struct. Mol. Biol.
  doi: 10.1038/nsmb808
  contributor:
    fullname: Keatinge-Clay A. T.
– volume: 103
  start-page: 16728
  year: 2006
  ident: ref3/cit3
  publication-title: Proc. Natl. Acad. Sci. U.S.A.
  doi: 10.1073/pnas.0604112103
  contributor:
    fullname: Crawford J. M.
– volume: 129
  start-page: 36
  year: 2007
  ident: ref23/cit23
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja0672122
  contributor:
    fullname: Zhu X.
– volume: 18
  start-page: 380
  year: 2001
  ident: ref2/cit2
  publication-title: Nat. Prod. Rep.
  doi: 10.1039/a909079g
  contributor:
    fullname: Staunton J.
– start-page: 282
  year: 1974
  ident: ref6/cit6
  publication-title: J. Chem. Soc., Chem. Commun.
  doi: 10.1039/c39740000282
  contributor:
    fullname: McInnes A.
– volume: 126
  start-page: 4534
  year: 2004
  ident: ref28/cit28
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja0317271
  contributor:
    fullname: Zha W.
– volume: 288
  start-page: 839
  year: 1992
  ident: ref29/cit29
  publication-title: Biochem. J.
  doi: 10.1042/bj2880839
  contributor:
    fullname: Spencer J.
– volume: 320
  start-page: 243
  year: 2008
  ident: ref5/cit5
  publication-title: Science
  doi: 10.1126/science.1154711
  contributor:
    fullname: Crawford J. M.
– volume: 461
  start-page: 1139
  year: 2009
  ident: ref4/cit4
  publication-title: Nature
  doi: 10.1038/nature08475
  contributor:
    fullname: Crawford J. M.
– volume: 3
  start-page: 833
  year: 1996
  ident: ref18/cit18
  publication-title: Chem. Biol.
  doi: 10.1016/S1074-5521(96)90069-1
  contributor:
    fullname: Oliynyk M.
– volume: 55
  start-page: 4090
  year: 1977
  ident: ref31/cit31
  publication-title: Can. J. Chem.
  doi: 10.1139/v77-580
  contributor:
    fullname: Wat C.-K.
– volume: 48
  start-page: 8746
  year: 2009
  ident: ref11/cit11
  publication-title: Biochemistry
  doi: 10.1021/bi901123r
  contributor:
    fullname: Liu X.
– volume: 46
  start-page: 5331
  year: 2010
  ident: ref25/cit25
  publication-title: Chem. Commun.
  doi: 10.1039/c0cc01162b
  contributor:
    fullname: Fisch K. M.
– volume: 132
  start-page: 13604
  year: 2010
  ident: ref30/cit30
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja107084d
  contributor:
    fullname: Xu W.
– volume: 63
  start-page: 947
  year: 2007
  ident: ref21/cit21
  publication-title: Acta Crystallogr. F
  doi: 10.1107/S1744309107047069
  contributor:
    fullname: Morita H.
– volume: 130
  start-page: 17988
  year: 2008
  ident: ref15/cit15
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja807052c
  contributor:
    fullname: Halo L. M.
– volume: 130
  start-page: 11149
  year: 2008
  ident: ref10/cit10
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja803078z
  contributor:
    fullname: Sims J. W.
– volume: 27
  start-page: 255
  year: 2010
  ident: ref12/cit12
  publication-title: Nat. Prod. Rep.
  doi: 10.1039/B912037H
  contributor:
    fullname: Du L.
– volume: 11
  start-page: 1508
  year: 2010
  ident: ref19/cit19
  publication-title: ChemBioChem
  doi: 10.1002/cbic.201000259
  contributor:
    fullname: Heneghan M. N.
– volume: 11
  start-page: 888
  year: 2004
  ident: ref34/cit34
  publication-title: Nat. Struct. Mol. Biol.
  doi: 10.1038/nsmb808
  contributor:
    fullname: Keatinge-Clay A. T.
– volume: 101
  start-page: 15567
  year: 2004
  ident: ref24/cit24
  publication-title: Proc. Natl. Acad. Sci. U.S.A.
  doi: 10.1073/pnas.0406901101
  contributor:
    fullname: Chakravarty B.
– volume: 321
  start-page: 1315
  year: 2008
  ident: ref16/cit16
  publication-title: Science
  doi: 10.1126/science.1161269
  contributor:
    fullname: Maier T.
– volume: 8
  start-page: 289
  year: 2007
  ident: ref9/cit9
  publication-title: ChemBioChem
  doi: 10.1002/cbic.200600398
  contributor:
    fullname: Eley K. L.
– start-page: 4053
  year: 2007
  ident: ref26/cit26
  publication-title: Chem. Commun.
  doi: 10.1039/b708614h
  contributor:
    fullname: Bailey A. M.
– volume: 33
  start-page: 859
  year: 2006
  ident: ref22/cit22
  publication-title: J. Ind. Microbiol. Biotechnol.
  doi: 10.1007/s10295-006-0137-9
  contributor:
    fullname: Zhu X.
– volume: 9
  start-page: 585
  year: 2008
  ident: ref14/cit14
  publication-title: ChemBioChem
  doi: 10.1002/cbic.200700390
  contributor:
    fullname: Halo L. M.
– volume: 326
  start-page: 589
  year: 2009
  ident: ref32/cit32
  publication-title: Science
  doi: 10.1126/science.1175602
  contributor:
    fullname: Ma S. M.
– volume: 54
  start-page: 9195
  year: 1998
  ident: ref13/cit13
  publication-title: Tetrahedron
  doi: 10.1016/S0040-4020(98)00557-2
  contributor:
    fullname: Moore M.
– volume: 2
  start-page: 972
  year: 2011
  ident: ref7/cit7
  publication-title: Chem. Sci.
  doi: 10.1039/c1sc00023c
  contributor:
    fullname: Heneghan M. N.
– volume: 50
  start-page: 4222
  year: 2011
  ident: ref8/cit8
  publication-title: Angew. Chem., Int. Ed.
  doi: 10.1002/anie.201007671
  contributor:
    fullname: Jessen H. J.
– volume: 6
  start-page: 680
  year: 2010
  ident: ref27/cit27
  publication-title: Mol. BioSyst.
  doi: 10.1039/b923990a
  contributor:
    fullname: Skellam E. J.
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Snippet The mechanism of programming of iterative highly reducing polyketide synthases remains one of the key unsolved problems of secondary metabolism. We conducted...
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SubjectTerms Aspergillus oryzae - enzymology
Chemistry
Chemistry, Multidisciplinary
Models, Molecular
Oxidation-Reduction
Physical Sciences
Polyketide Synthases - chemistry
Polyketide Synthases - metabolism
Pyridones - chemistry
Pyridones - metabolism
Science & Technology
Title Rational Domain Swaps Decipher Programming in Fungal Highly Reducing Polyketide Synthases and Resurrect an Extinct Metabolite
URI http://dx.doi.org/10.1021/ja206914q
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https://www.ncbi.nlm.nih.gov/pubmed/21899331
https://search.proquest.com/docview/898152584
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