A Fed-Batch Synthetic Strategy for a Three-Step Enzymatic Synthesis of Poly-epsilon-caprolactone

Scherkus C, Schmidt S, Bornscheuer UT, Gröger H, Kara S, Liese A (2016)
CHEMCATCHEM 8(22): 3446-3452.

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A three-step enzymatic reaction sequence for the synthesis of poly-epsilon-caprolactone (PCL) was designed running in a fed-batch operation. The first part of the cascade consisted of two oxidation steps starting with alcohol dehydrogenase catalyzed oxidation from cyclohexanol to cyclohexanone and further oxidation to epsilon-caprolactone (ECL) by means of a Baeyer-Villiger monooxygenase. As a third step, lipase-catalyzed hydrolysis of the lactone to 6-hydroxyhexanoic acid (6-HHA) was designed. With this biocatalytic multistep process reported herein, severe substrate surplus and product inhibition could be circumvented by the fed-batch operation by adding the cyclohexanol substrate and by in situ product removal of ECL by hydrolysis, respectively. Up to 283 mm product concentration of 6-HHA was reached in the fed-batch operated process without loss in productivity within 20 h. After extraction and subsequent polymerization catalyzed by Candida antarctica lipase B, analysis of the unfractionated polymer revealed a bimodal distribution of the polymer population, which reached a mass average molar mass (M-w) value of approximately 63 000 g mol(-1) and a dispersity (M-w/M-n) of 1.1 for the higher molecular weight population, which thus revealed an alternative route to the conventional synthesis of PCL.
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Scherkus C, Schmidt S, Bornscheuer UT, Gröger H, Kara S, Liese A. A Fed-Batch Synthetic Strategy for a Three-Step Enzymatic Synthesis of Poly-epsilon-caprolactone. CHEMCATCHEM. 2016;8(22):3446-3452.
Scherkus, C., Schmidt, S., Bornscheuer, U. T., Gröger, H., Kara, S., & Liese, A. (2016). A Fed-Batch Synthetic Strategy for a Three-Step Enzymatic Synthesis of Poly-epsilon-caprolactone. CHEMCATCHEM, 8(22), 3446-3452. doi:10.1002/cctc.201600806
Scherkus, C., Schmidt, S., Bornscheuer, U. T., Gröger, H., Kara, S., and Liese, A. (2016). A Fed-Batch Synthetic Strategy for a Three-Step Enzymatic Synthesis of Poly-epsilon-caprolactone. CHEMCATCHEM 8, 3446-3452.
Scherkus, C., et al., 2016. A Fed-Batch Synthetic Strategy for a Three-Step Enzymatic Synthesis of Poly-epsilon-caprolactone. CHEMCATCHEM, 8(22), p 3446-3452.
C. Scherkus, et al., “A Fed-Batch Synthetic Strategy for a Three-Step Enzymatic Synthesis of Poly-epsilon-caprolactone”, CHEMCATCHEM, vol. 8, 2016, pp. 3446-3452.
Scherkus, C., Schmidt, S., Bornscheuer, U.T., Gröger, H., Kara, S., Liese, A.: A Fed-Batch Synthetic Strategy for a Three-Step Enzymatic Synthesis of Poly-epsilon-caprolactone. CHEMCATCHEM. 8, 3446-3452 (2016).
Scherkus, Christian, Schmidt, Sandy, Bornscheuer, Uwe T., Gröger, Harald, Kara, Selin, and Liese, Andreas. “A Fed-Batch Synthetic Strategy for a Three-Step Enzymatic Synthesis of Poly-epsilon-caprolactone”. CHEMCATCHEM 8.22 (2016): 3446-3452.
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