Biocatalytic synthesis of polyesters from sugar-based building blocks using immobilized Candida antarctica lipase B
The synthesis of linear ester oligomers (LEOs) and cyclic ester oligomers (CEOs) from non-activated succinic acid (A) in combination with di-anhydro hexitols (B, DAH) in a toluene based medium using immobilized Candida antarctica lipase B (CAL B), was studied. The conversion is highest for isomannid...
Published in: | Journal of Molecular Catalysis B: Enzymatic |
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Main Authors: | , , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
2011
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Subjects: | |
Online Access: | https://research.wur.nl/en/publications/biocatalytic-synthesis-of-polyesters-from-sugar-based-building-bl https://doi.org/10.1016/j.molcatb.2011.02.015 |
Summary: | The synthesis of linear ester oligomers (LEOs) and cyclic ester oligomers (CEOs) from non-activated succinic acid (A) in combination with di-anhydro hexitols (B, DAH) in a toluene based medium using immobilized Candida antarctica lipase B (CAL B), was studied. The conversion is highest for isomannide and decreases in the order isomannide > isosorbide isoidide. These experimental results were corroborated by substrate-imprinted docking indicating that the hydroxyl group oriented inwards the “V”-shaped plane of the DAHs (endo-hydroxyl) is preferred over the outwards oriented hydroxyl group (exo-hydroxyl) by CAL B. The maximum conversions under optimized conditions were 88.2% and 93.7% for succinic acid and isomannide, respectively. MALDI-TOF detected products at 24 h were a mixture of cyclic (35.1%) and linear ester oligomers (64.9%). Cyclic ester oliogomers were the most abundant products during the first 8 h of reaction (32.5–48.7%), where the first cyclic of the series (CEO1) was the most predominant cyclic product (23–40%). |
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