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Sökning: WFRF:(Olsén Arne) > Kungliga Tekniska Högskolan

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1.
  • Stamm, Arne, et al. (författare)
  • A retrobiosynthesis-based route to generate pinene-derived polyesters
  • 2019
  • Ingår i: ChemBioChem (Print). - : Wiley. - 1439-4227 .- 1439-7633. ; 20, s. 1664-1671
  • Tidskriftsartikel (refereegranskat)abstract
    • 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.
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2.
  • Stamm, Arne, et al. (författare)
  • Pinene-Based Oxidative Synthetic Toolbox for Scalable Polyester Synthesis
  • 2021
  • Ingår i: JACS Au. - : American Chemical Society (ACS). - 2691-3704. ; 1:11, s. 1949-1960
  • Tidskriftsartikel (refereegranskat)abstract
    • Generation of renewable polymers is a long-standing goal toward reaching a more sustainable society, but building blocks in biomass can be incompatible with desired polymerization type, hampering the full implementation potential of biomaterials. Herein, we show how conceptually simple oxidative transformations can be used to unlock the inherent reactivity of terpene synthons in generating polyesters by two different mechanisms starting from the same alpha-pinene substrate. In the first pathway, alpha-pinene was oxidized into the bicyclic verbanone-based lactone and subsequently polymerized into star-shaped polymers via ring-opening polymerization, resulting in a biobased semicrystalline polyester with tunable glass transition and melting temperatures. In a second pathway, polyesters were synthesized via polycondensation, utilizing the diol 1-(1'-chydroxyethyl)-3-(2'-hydroxyethyl)-2,2-dimethylcyclobutane (HHDC) synthesized by oxidative cleavage of the double bond of alpha-pinene, together with unsaturated biobased diesters such as dimethyl maleate (DMM) and dimethyl itaconate (DMI). The resulting families of terpenebased polyesters were thereafter successfully cross-Iinked by either transetherification, utilizing the terminal hydroxyl groups of the synthesized verbanone-based materials, or by UV irradiation, utilizing the unsaturation provided by the DMM or DMI moieties within the HHDC-based copolymers. This work highlights the potential to apply an oxidative toolbox to valorize inert terpene metabolites enabling generation of biosourced polyesters and coatings thereof by complementary mechanisms.
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