A Retro-biosynthesis-Based Route to Generate Pinene-Derived Polyesters

Chembiochem : a European Journal of Chemical Biology
Arne StammPer-Olof Syrén

Abstract

Significantly increased production of biobased polymers is a prerequisite to replace petroleum-based materials towards reaching a circular bioeconomy. However, many renewable building blocks from wood and other plant material are not directly amenable for polymerization, due to their inert backbones and/or lack of functional group compatibility with the desired polymerization type. Based on a retro-biosynthetic analysis of polyesters, a chemoenzymatic route from (-)-α-pinene towards a verbanone-based lactone, which is further used in ring-opening polymerization, is presented. Generated pinene-derived polyesters showed elevated degradation and glass transition temperatures, compared with poly(ϵ-decalactone), which lacks a ring structure in its backbone. Semirational enzyme engineering of the cyclohexanone monooxygenase from Acinetobacter calcoaceticus enabled the biosynthesis of the key lactone intermediate for the targeted polyester. As a proof of principle, one enzyme variant identified from screening in a microtiter plate was used in biocatalytic upscaling, which afforded the bicyclic lactone in 39 % conversion in shake flask scale reactions.

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Citations

Aug 31, 2021·RSC Chemical Biology·Mélanie Hall

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Methods Mentioned

BETA
NMR
size exclusion chromatography
differential scanning calorimetry
protein assay

Software Mentioned

AutoSMILES
CHMO
YASARA

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