An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers

Schmidt S, Scherkus C, Muschiol J, Menyes U, Winkler T, Hummel W, Gröger H, Liese A, Herz H-G, Bornscheuer UT (2015)
Angewandte Chemie (International ed. in English) 54(9): 2784-2787.

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Poly-ε-caprolactone (PCL) is chemically produced on an industrial scale in spite of the need for hazardous peracetic acid as an oxidation reagent. Although Baeyer-Villiger monooxygenases (BVMO) in principle enable the enzymatic synthesis of ε-caprolactone (ε-CL) directly from cyclohexanone with molecular oxygen, current systems suffer from low productivity and are subject to substrate and product inhibition. The major limitations for such a biocatalytic route to produce this bulk chemical were overcome by combining an alcohol dehydrogenase with a BVMO to enable the efficient oxidation of cyclohexanol to ε-CL. Key to success was a subsequent direct ring-opening oligomerization of in situ formed ε-CL in the aqueous phase by using lipase A from Candida antarctica, thus efficiently solving the product inhibition problem and leading to the formation of oligo-ε-CL at more than 20 g L(-1) when starting from 200 mM cyclohexanol. This oligomer is easily chemically polymerized to PCL.
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Schmidt S, Scherkus C, Muschiol J, et al. An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers. Angewandte Chemie (International ed. in English). 2015;54(9):2784-2787.
Schmidt, S., Scherkus, C., Muschiol, J., Menyes, U., Winkler, T., Hummel, W., Gröger, H., et al. (2015). An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers. Angewandte Chemie (International ed. in English), 54(9), 2784-2787. doi:10.1002/anie.201410633
Schmidt, S., Scherkus, C., Muschiol, J., Menyes, U., Winkler, T., Hummel, W., Gröger, H., Liese, A., Herz, H. - G., and Bornscheuer, U. T. (2015). An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers. Angewandte Chemie (International ed. in English) 54, 2784-2787.
Schmidt, S., et al., 2015. An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers. Angewandte Chemie (International ed. in English), 54(9), p 2784-2787.
S. Schmidt, et al., “An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers”, Angewandte Chemie (International ed. in English), vol. 54, 2015, pp. 2784-2787.
Schmidt, S., Scherkus, C., Muschiol, J., Menyes, U., Winkler, T., Hummel, W., Gröger, H., Liese, A., Herz, H.-G., Bornscheuer, U.T.: An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers. Angewandte Chemie (International ed. in English). 54, 2784-2787 (2015).
Schmidt, Sandy, Scherkus, Christian, Muschiol, Jan, Menyes, Ulf, Winkler, Till, Hummel, Werner, Gröger, Harald, Liese, Andreas, Herz, Hans-Georg, and Bornscheuer, Uwe T. “An Enzyme Cascade Synthesis of ε-Caprolactone and its Oligomers”. Angewandte Chemie (International ed. in English) 54.9 (2015): 2784-2787.
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17 Citations in Europe PMC

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