Polyketide bio-derivatization using the promiscuous acyltransferase KirCII
During polyketide biosynthesis, acyltransferases (ATs) are the essential gatekeepers which provide the assembly lines with precursors and thus contribute greatly to structural diversity. Previously, we demonstrated that the discrete AT KirCII from the kirromycin antibiotic pathway accesses non-malon...
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| Published in | ACS synthetic biology Vol. 6; no. 3; pp. 421 - 427 |
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| Main Authors | , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
22.02.2017
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| Online Access | Get full text |
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| Abstract | During polyketide biosynthesis, acyltransferases (ATs) are the essential gatekeepers which provide the assembly lines with precursors and thus contribute greatly to structural diversity. Previously, we demonstrated that the discrete AT KirCII from the kirromycin antibiotic pathway accesses non-malonate extender units. Here, we exploit the promiscuity of KirCII to generate new kirromycins with allyl- and propargyl-side chains
in vivo
, the latter were utilized as educts for further modification by ‘click’ chemistry. |
|---|---|
| AbstractList | During polyketide biosynthesis, acyltransferases (ATs) are the essential gatekeepers which provide the assembly lines with precursors and thus contribute greatly to structural diversity. Previously, we demonstrated that the discrete AT KirCII from the kirromycin antibiotic pathway accesses non-malonate extender units. Here, we exploit the promiscuity of KirCII to generate new kirromycins with allyl- and propargyl-side chains
in vivo
, the latter were utilized as educts for further modification by ‘click’ chemistry. |
| Author | Grond, Stephanie Weber, Tilmann Kulik, Andreas Schafhauser, Thomas McArthur, John Wohlleben, Wolfgang Härtner, Thomas Lee, Sang Yup Zubeil, Florian Williams, Gavin J. Musiol-Kroll, Ewa M. Koryakina, Irina |
| AuthorAffiliation | 3 Eberhard Karls Universität Tübingen, Institut für Organische Chemie, Auf der Morgenstelle 18, 72076 Tübingen, Germany 4 Eberhard Karls Universität Tübingen, Interfakultäres Institut für Mikrobiologie und Infektionsmedizin, Mikrobiologie/Biotechnologie, Auf der Morgenstelle 28, 72076 Tübingen, Germany 6 Department of Chemical and Biomolecular Engineering (BK21 Plus Program), Korea Advanced Institute of Science and Technology (KAIST), 291 Daehak-ro, Yuseong-gu, Daejeon 34141, Republic of Korea 1 Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, Kemitorvet B220, 2800 Kgs. Lyngby, Denmark 2 German Centre for Infection Research (DZIF), Partner site Tübingen, IMIT, Auf der Morgenstelle 28, 72076 Tübingen, Germany 5 North Carolina State University, Department of Chemistry, Raleigh, NC 27695-8204, USA |
| AuthorAffiliation_xml | – name: 6 Department of Chemical and Biomolecular Engineering (BK21 Plus Program), Korea Advanced Institute of Science and Technology (KAIST), 291 Daehak-ro, Yuseong-gu, Daejeon 34141, Republic of Korea – name: 1 Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, Kemitorvet B220, 2800 Kgs. Lyngby, Denmark – name: 4 Eberhard Karls Universität Tübingen, Interfakultäres Institut für Mikrobiologie und Infektionsmedizin, Mikrobiologie/Biotechnologie, Auf der Morgenstelle 28, 72076 Tübingen, Germany – name: 5 North Carolina State University, Department of Chemistry, Raleigh, NC 27695-8204, USA – name: 3 Eberhard Karls Universität Tübingen, Institut für Organische Chemie, Auf der Morgenstelle 18, 72076 Tübingen, Germany – name: 2 German Centre for Infection Research (DZIF), Partner site Tübingen, IMIT, Auf der Morgenstelle 28, 72076 Tübingen, Germany |
| Author_xml | – sequence: 1 givenname: Ewa M. surname: Musiol-Kroll fullname: Musiol-Kroll, Ewa M. organization: Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, Kemitorvet B220, 2800 Kgs. Lyngby, Denmark German Centre for Infection Research (DZIF), Partner site Tübingen, IMIT, Auf der Morgenstelle 28, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Institut für Organische Chemie, Auf der Morgenstelle 18, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Interfakultäres Institut für Mikrobiologie und Infektionsmedizin, Mikrobiologie/Biotechnologie, Auf der Morgenstelle 28, 72076 Tübingen, Germany North Carolina State University, Department of Chemistry, Raleigh, NC 27695-8204, USA Department of Chemical and Biomolecular Engineering (BK21 Plus Program), Korea Advanced Institute of Science and Technology (KAIST), 291 Daehak-ro, Yuseong-gu, Daejeon 34141, Republic of Korea – sequence: 2 givenname: Florian surname: Zubeil fullname: Zubeil, Florian organization: Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, Kemitorvet B220, 2800 Kgs. Lyngby, Denmark German Centre for Infection Research (DZIF), Partner site Tübingen, IMIT, Auf der Morgenstelle 28, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Institut für Organische Chemie, Auf der Morgenstelle 18, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Interfakultäres Institut für Mikrobiologie und Infektionsmedizin, Mikrobiologie/Biotechnologie, Auf der Morgenstelle 28, 72076 Tübingen, Germany North Carolina State University, Department of Chemistry, Raleigh, NC 27695-8204, USA Department of Chemical and Biomolecular Engineering (BK21 Plus Program), Korea Advanced Institute of Science and Technology (KAIST), 291 Daehak-ro, Yuseong-gu, Daejeon 34141, Republic of Korea – sequence: 3 givenname: Thomas surname: Schafhauser fullname: Schafhauser, Thomas organization: Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, Kemitorvet B220, 2800 Kgs. Lyngby, Denmark German Centre for Infection Research (DZIF), Partner site Tübingen, IMIT, Auf der Morgenstelle 28, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Institut für Organische Chemie, Auf der Morgenstelle 18, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Interfakultäres Institut für Mikrobiologie und Infektionsmedizin, Mikrobiologie/Biotechnologie, Auf der Morgenstelle 28, 72076 Tübingen, Germany North Carolina State University, Department of Chemistry, Raleigh, NC 27695-8204, USA Department of Chemical and Biomolecular Engineering (BK21 Plus Program), Korea Advanced Institute of Science and Technology (KAIST), 291 Daehak-ro, Yuseong-gu, Daejeon 34141, Republic of Korea – sequence: 4 givenname: Thomas surname: Härtner fullname: Härtner, Thomas organization: Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, Kemitorvet B220, 2800 Kgs. Lyngby, Denmark German Centre for Infection Research (DZIF), Partner site Tübingen, IMIT, Auf der Morgenstelle 28, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Institut für Organische Chemie, Auf der Morgenstelle 18, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Interfakultäres Institut für Mikrobiologie und Infektionsmedizin, Mikrobiologie/Biotechnologie, Auf der Morgenstelle 28, 72076 Tübingen, Germany North Carolina State University, Department of Chemistry, Raleigh, NC 27695-8204, USA Department of Chemical and Biomolecular Engineering (BK21 Plus Program), Korea Advanced Institute of Science and Technology (KAIST), 291 Daehak-ro, Yuseong-gu, Daejeon 34141, Republic of Korea – sequence: 5 givenname: Andreas surname: Kulik fullname: Kulik, Andreas organization: Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, Kemitorvet B220, 2800 Kgs. Lyngby, Denmark German Centre for Infection Research (DZIF), Partner site Tübingen, IMIT, Auf der Morgenstelle 28, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Institut für Organische Chemie, Auf der Morgenstelle 18, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Interfakultäres Institut für Mikrobiologie und Infektionsmedizin, Mikrobiologie/Biotechnologie, Auf der Morgenstelle 28, 72076 Tübingen, Germany North Carolina State University, Department of Chemistry, Raleigh, NC 27695-8204, USA Department of Chemical and Biomolecular Engineering (BK21 Plus Program), Korea Advanced Institute of Science and Technology (KAIST), 291 Daehak-ro, Yuseong-gu, Daejeon 34141, Republic of Korea – sequence: 6 givenname: John surname: McArthur fullname: McArthur, John organization: Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, Kemitorvet B220, 2800 Kgs. Lyngby, Denmark German Centre for Infection Research (DZIF), Partner site Tübingen, IMIT, Auf der Morgenstelle 28, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Institut für Organische Chemie, Auf der Morgenstelle 18, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Interfakultäres Institut für Mikrobiologie und Infektionsmedizin, Mikrobiologie/Biotechnologie, Auf der Morgenstelle 28, 72076 Tübingen, Germany North Carolina State University, Department of Chemistry, Raleigh, NC 27695-8204, USA Department of Chemical and Biomolecular Engineering (BK21 Plus Program), Korea Advanced Institute of Science and Technology (KAIST), 291 Daehak-ro, Yuseong-gu, Daejeon 34141, Republic of Korea – sequence: 7 givenname: Irina surname: Koryakina fullname: Koryakina, Irina organization: Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, Kemitorvet B220, 2800 Kgs. Lyngby, Denmark German Centre for Infection Research (DZIF), Partner site Tübingen, IMIT, Auf der Morgenstelle 28, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Institut für Organische Chemie, Auf der Morgenstelle 18, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Interfakultäres Institut für Mikrobiologie und Infektionsmedizin, Mikrobiologie/Biotechnologie, Auf der Morgenstelle 28, 72076 Tübingen, Germany North Carolina State University, Department of Chemistry, Raleigh, NC 27695-8204, USA Department of Chemical and Biomolecular Engineering (BK21 Plus Program), Korea Advanced Institute of Science and Technology (KAIST), 291 Daehak-ro, Yuseong-gu, Daejeon 34141, Republic of Korea – sequence: 8 givenname: Wolfgang surname: Wohlleben fullname: Wohlleben, Wolfgang organization: Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, Kemitorvet B220, 2800 Kgs. Lyngby, Denmark German Centre for Infection Research (DZIF), Partner site Tübingen, IMIT, Auf der Morgenstelle 28, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Institut für Organische Chemie, Auf der Morgenstelle 18, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Interfakultäres Institut für Mikrobiologie und Infektionsmedizin, Mikrobiologie/Biotechnologie, Auf der Morgenstelle 28, 72076 Tübingen, Germany North Carolina State University, Department of Chemistry, Raleigh, NC 27695-8204, USA Department of Chemical and Biomolecular Engineering (BK21 Plus Program), Korea Advanced Institute of Science and Technology (KAIST), 291 Daehak-ro, Yuseong-gu, Daejeon 34141, Republic of Korea – sequence: 9 givenname: Stephanie surname: Grond fullname: Grond, Stephanie organization: Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, Kemitorvet B220, 2800 Kgs. Lyngby, Denmark German Centre for Infection Research (DZIF), Partner site Tübingen, IMIT, Auf der Morgenstelle 28, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Institut für Organische Chemie, Auf der Morgenstelle 18, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Interfakultäres Institut für Mikrobiologie und Infektionsmedizin, Mikrobiologie/Biotechnologie, Auf der Morgenstelle 28, 72076 Tübingen, Germany North Carolina State University, Department of Chemistry, Raleigh, NC 27695-8204, USA Department of Chemical and Biomolecular Engineering (BK21 Plus Program), Korea Advanced Institute of Science and Technology (KAIST), 291 Daehak-ro, Yuseong-gu, Daejeon 34141, Republic of Korea – sequence: 10 givenname: Gavin J. surname: Williams fullname: Williams, Gavin J. organization: Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, Kemitorvet B220, 2800 Kgs. Lyngby, Denmark German Centre for Infection Research (DZIF), Partner site Tübingen, IMIT, Auf der Morgenstelle 28, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Institut für Organische Chemie, Auf der Morgenstelle 18, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Interfakultäres Institut für Mikrobiologie und Infektionsmedizin, Mikrobiologie/Biotechnologie, Auf der Morgenstelle 28, 72076 Tübingen, Germany North Carolina State University, Department of Chemistry, Raleigh, NC 27695-8204, USA Department of Chemical and Biomolecular Engineering (BK21 Plus Program), Korea Advanced Institute of Science and Technology (KAIST), 291 Daehak-ro, Yuseong-gu, Daejeon 34141, Republic of Korea – sequence: 11 givenname: Sang Yup surname: Lee fullname: Lee, Sang Yup organization: Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, Kemitorvet B220, 2800 Kgs. Lyngby, Denmark German Centre for Infection Research (DZIF), Partner site Tübingen, IMIT, Auf der Morgenstelle 28, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Institut für Organische Chemie, Auf der Morgenstelle 18, 72076 Tübingen, Germany Eberhard Karls Universität Tübingen, Interfakultäres Institut für Mikrobiologie und Infektionsmedizin, Mikrobiologie/Biotechnologie, Auf der Morgenstelle 28, 72076 Tübingen, Germany North Carolina State University, Department of Chemistry, Raleigh, NC 27695-8204, USA Department of Chemical and Biomolecular Engineering (BK21 Plus Program), Korea Advanced Institute of Science and Technology (KAIST), 291 Daehak-ro, Yuseong-gu, Daejeon 34141, Republic of Korea – sequence: 12 givenname: Tilmann surname: Weber fullname: Weber, Tilmann organization: Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, Kemitorvet B220, 2800 Kgs. 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| Notes | Present address: Department of Chemistry, University of California, One Shields Avenue, Davis, USA Equal contribution Present address: Intrexon Corporation, South San Francisco, California, USA |
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| Snippet | During polyketide biosynthesis, acyltransferases (ATs) are the essential gatekeepers which provide the assembly lines with precursors and thus contribute... |
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| Title | Polyketide bio-derivatization using the promiscuous acyltransferase KirCII |
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