Biochemical and Structural Basis for Controlling Chemical Modularity in Fungal Polyketide Biosynthesis
Modular collaboration between iterative fungal polyketide synthases (IPKSs) is an important mechanism for generating structural diversity of polyketide natural products. Inter-PKS communication and substrate channeling are controlled in large by the starter unit acyl carrier protein transacylase (SA...
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| Published in | Journal of the American Chemical Society Vol. 137; no. 31; pp. 9885 - 9893 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
12.08.2015
Amer Chemical Soc American Chemical Society (ACS) |
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| Online Access | Get full text |
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| Abstract | Modular collaboration between iterative fungal polyketide synthases (IPKSs) is an important mechanism for generating structural diversity of polyketide natural products. Inter-PKS communication and substrate channeling are controlled in large by the starter unit acyl carrier protein transacylase (SAT) domain found in the accepting IPKS module. Here, we reconstituted the modular biosynthesis of the benzaldehyde core of the chaetoviridin and chaetomugilin azaphilone natural products using the IPKSs CazF and CazM. Our studies revealed a critical role of CazM’s SAT domain in selectively transferring a highly reduced triketide product from CazF. In contrast, a more oxidized triketide that is also produced by CazF and required in later stages of biosynthesis of the final product is not recognized by the SAT domain. The structural basis for the acyl unit selectivity was uncovered by the first X-ray structure of a fungal SAT domain, highlighted by a covalent hexanoyl thioester intermediate in the SAT active site. The crystal structure of SAT domain will enable protein engineering efforts aimed at mixing and matching different IPKS modules for the biosynthesis of new compounds. |
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| AbstractList | Modular collaboration between iterative fungal polyketide synthases (IPKSs) is an important mechanism for generating structural diversity of polyketide natural products. Inter-PKS communication and substrate channeling are controlled in large by the starter unit acyl carrier protein transacylase (SAT) domain found in the accepting IPKS module. Here, we reconstituted the modular biosynthesis of the benzaldehyde core of the chaetoviridin and chaetomugilin azaphilone natural products using the IPKSs CazF and CazM. Our studies revealed a critical role of CazM’s SAT domain in selectively transferring a highly reduced triketide product from CazF. In contrast, a more oxidized triketide that is also produced by CazF and required in later stages of biosynthesis of the final product is not recognized by the SAT domain. The structural basis for the acyl unit selectivity was uncovered by the first X-ray structure of a fungal SAT domain, highlighted by a covalent hexanoyl thioester intermediate in the SAT active site. The crystal structure of SAT domain will enable protein engineering efforts aimed at mixing and matching different IPKS modules for the biosynthesis of new compounds. Modular collaboration between iterative fungal polyketide synthases (IPKSs) is an important mechanism for generating structural diversity of polyketide natural products. Inter-PKS communication and substrate channeling are controlled in large by the starter unit acyl carrier protein transacylase (SAT) domain found in the accepting IPKS module. Here in this study, we reconstituted the modular biosynthesis of the benzaldehyde core of the chaetoviridin and chaetomugilin azaphilone natural products using the IPKSs CazF and CazM. Our studies revealed a critical role of CazM’s SAT domain in selectively transferring a highly reduced triketide product from CazF. In contrast, a more oxidized triketide that is also produced by CazF and required in later stages of biosynthesis of the final product is not recognized by the SAT domain. The structural basis for the acyl unit selectivity was uncovered by the first X-ray structure of a fungal SAT domain, highlighted by a covalent hexanoyl thioester intermediate in the SAT active site. Finally, the crystal structure of SAT domain will enable protein engineering efforts aimed at mixing and matching different IPKS modules for the biosynthesis of new compounds. |
| Author | Dietrich, David Cascio, Duilio Vederas, John C Sawaya, Michael R Watanabe, Kenji Winter, Jaclyn M Sato, Michio Tang, Yi |
| AuthorAffiliation | Department of Chemistry University of Alberta Department of Pharmaceutical Sciences Department of Chemistry and Biochemistry Department of Chemical and Biomolecular Engineering University of California Department of Energy (DOE) Institute for Genomics and Proteomics University of Shizuoka |
| AuthorAffiliation_xml | – name: University of Alberta – name: University of California – name: Department of Chemistry – name: Department of Chemical and Biomolecular Engineering – name: University of Shizuoka – name: Department of Pharmaceutical Sciences – name: Department of Energy (DOE) Institute for Genomics and Proteomics – name: Department of Chemistry and Biochemistry – name: Department of Pharmaceutical Sciences, University of Shizuoka, Shizuoka, Japan 422-8526 – name: Department of Energy (DOE) Institute for Genomics and Proteomics, University of California, Los Angeles, California 90095 – name: Δ Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095 – name: Department of Chemical and Biomolecular Engineering, University of California, Los Angeles, California 90095 – name: Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2 |
| Author_xml | – sequence: 1 givenname: Jaclyn M surname: Winter fullname: Winter, Jaclyn M – sequence: 2 givenname: Duilio surname: Cascio fullname: Cascio, Duilio – sequence: 3 givenname: David surname: Dietrich fullname: Dietrich, David – sequence: 4 givenname: Michio surname: Sato fullname: Sato, Michio – sequence: 5 givenname: Kenji surname: Watanabe fullname: Watanabe, Kenji – sequence: 6 givenname: Michael R surname: Sawaya fullname: Sawaya, Michael R – sequence: 7 givenname: John C surname: Vederas fullname: Vederas, John C – sequence: 8 givenname: Yi surname: Tang fullname: Tang, Yi email: yitang@ucla.edu |
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| Snippet | Modular collaboration between iterative fungal polyketide synthases (IPKSs) is an important mechanism for generating structural diversity of polyketide natural... |
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| SubjectTerms | BASIC BIOLOGICAL SCIENCES Chaetomium - enzymology Chemistry Chemistry, Multidisciplinary INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY Models, Molecular Physical Sciences Polyketide Synthases - chemistry Polyketide Synthases - metabolism Polyketides - metabolism Protein Structure, Tertiary Science & Technology |
| Title | Biochemical and Structural Basis for Controlling Chemical Modularity in Fungal Polyketide Biosynthesis |
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