Biocatalytic synthesis of polyesters from sugar-based building blocks using immobilized Candida antarctica lipase B

• Published in: Journal of Molecular Catalysis B: Enzymatic
• Main Authors: Habeych Narvaez, D.I., Juhl, P.B., Pleiss, J., Vanegas, D.M., Eggink, G., Boeriu, C.G.
• Format: Article in Journal/Newspaper
• Language: English
• Published: 2011
• Subjects: 3(s)-isopropylmorpholine-2,5-dione; dynamic kinetic resolution; esterification; isoidide; isomannide; isosorbide; oligomers; organic medium; ring-opening polymerization; secondary alcohols; Antarc*; Antarctica
• 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

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%).