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Engineering of Transmembrane Alkane Monooxygenases to Improve a Key Reaction Step in the Synthesis of Polymer Precursor Tulipalin A
Open accessPreprint — published as 10.1002/anie.202503464 · Paper page
Abstract
The α-methylene-γ-butyrolactone tulipalin A, naturally found in tulips can polymerize via addition at the vinyl group or via ring-opening polymerization, making it a highly promising monomer for biobased polymers. As tulipalin A biosynthesis in plants remains elusive, we propose a pathway for its synthesis starting from the metabolic intermediate isoprenol. For this, terminal hydroxylation of the α-methylene substrate isoprenyl acetate is a decisive step. While a panel of fungal unspecific peroxygenases showed a preference for the undesired epoxidation of the exo- olefin group, bacterial alkane monooxygenases were specific for terminal hydroxylation. A combination of protein engineering based on de novo structure prediction of the membrane enzymes with cell engineering allowed to increase the specific activity by 6-fold to 1.83 U g cdw -1 , unlocking this reaction for the fermentative production of tulipalin A from renewable resources.
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Metadata
- Authors
- Nigl, A., Delsoglio, V., Grgić, M., Malihan-Yap, L., Myrtollari, K., Spasic, J., Winkler, M., Oberdorfer, G., Taden, A., Anić, I., & Kourist, R.
- Affiliations
- Graz University of Technology (AT)
- Henkel (Germany) (DE)
- Corresponding author
- Kourist, Robert
- ORCID
- Venue
- Angewandte Chemie International Edition
- Publisher
- openRxiv
- Published
- 2024-07-08
- Volume
- 64
- Issue
- 25
- Pages
- e202503464-e202503464
- ISSN
- 1433-7851 (ISSN-L)
- PMC
- PMC12171333
- OpenAlex
- W4408707485
- Cited by
- 9
- References
- 1
- Citations by year
- 2026: 8 · 2025: 1
- FWCI
- 2.71
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- cc-by
- Locations
- Angewandte Chemie International Edition (publishedVersion, cc-by)
- bioRxiv (Cold Spring Harbor Laboratory) (acceptedVersion, cc-by-nc-nd)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- Funders
- TU Graz, Internationale Beziehungen und Mobilitätsprogramme
- Amt der NÖ Landesregierung
- European Commission (101135542)
- Österreichische Forschungsförderungsgesellschaft (91013)
- Standortagentur Tirol
- Bundesministerium für Digitalisierung und Wirtschaftsstandort
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Enzyme Catalysis and Immobilization
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biotechnology › Biochemical and biochemical processes
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Microbial Metabolic Engineering and Bioproduction
- Keywords
- alkane monooxygenase, protein engineering, terpenoid biosynthesis, allylic alcohol oxidation, ring-opening polymerization, bio-based polymers, fungal peroxygenases, de novo structure prediction, cell engineering, lactonization
- MeSH terms
- Mixed Function Oxygenases, Polymers, 4-Butyrolactone, Protein Engineering
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