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A retrobiosynthesis-based route to generate pinene-derived polyesters
KTH, Centres, Science for Life Laboratory, SciLifeLab. KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.ORCID iD: 0000-0001-8727-2102
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology. KTH, Centres, Science for Life Laboratory, SciLifeLab.
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology. KTH, Centres, Science for Life Laboratory, SciLifeLab.
Holmen AB, Dev, S-89180 Östersund, Sweden.
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2019 (English)In: ChemBioChem (Print), ISSN 1439-4227, E-ISSN 1439-7633, Vol. 20, p. 1664-1671Article in journal (Refereed) Published
Abstract [en]

Significantly increased production of biobased polymers is aprerequisite to replace petroleum-based materials towardsreaching a circular bioeconomy. However, many renewablebuilding blocks from wood and other plant material are notdirectly amenable for polymerization, due to their inert backbonesand/or lack of functional group compatibility with thedesired polymerization type. Based on a retro-biosyntheticanalysis of polyesters, a chemoenzymatic route from (@)-apinenetowards a verbanone-based lactone, which is furtherused in ring-opening polymerization, is presented. Generatedpinene-derived polyesters showed elevated degradation andglass transition temperatures, compared with poly(e-decalactone),which lacks a ring structure in its backbone. Semirationalenzyme engineering of the cyclohexanone monooxygenasefrom Acinetobacter calcoaceticus enabled the biosynthesis ofthe key lactone intermediate for the targeted polyester. As aproof of principle, one enzyme variant identified from screeningin a microtiter plate was used in biocatalytic upscaling,which afforded the bicyclic lactone in 39% conversion in shakeflask scale reactions.

Place, publisher, year, edition, pages
2019. Vol. 20, p. 1664-1671
National Category
Polymer Chemistry
Research subject
Biotechnology
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URN: urn:nbn:se:kth:diva-260797DOI: 10.1002/cbic.201900046ISI: 000477916100008Scopus ID: 2-s2.0-85066903140OAI: oai:DiVA.org:kth-260797DiVA, id: diva2:1356085
Note

QC 20191008

Available from: 2019-09-30 Created: 2019-09-30 Last updated: 2019-10-08Bibliographically approved

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Stamm, ArneBiundo, AntoninoSchmidt, BjörnOlsén, PeterFogelström, LindaMalmström, EvaSyrén, Per-Olof

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Science for Life Laboratory, SciLifeLabCoating TechnologyFibre- and Polymer TechnologyWallenberg Wood Science CenterProtein Science
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