Process Development through Solvent Engineering in the Biocatalytic Synthesis of the Heterocyclic Bulk Chemical epsilon-Caprolactone

Reimer A, Wedde S, Staudt S, Schmidt S, Hoeffer D, Hummel W, Kragl U, Bornscheuer UT, Gröger H (2017)
JOURNAL OF HETEROCYCLIC CHEMISTRY 54(1): 391-396.

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For an alternative synthetic approach toward the heterocyclic industrial chemical e-caprolactone, which is based on a biocatalytic oxidation of readily available cyclohexanol with air in aqueous media (using an alcohol dehydrogenase and a Baeyer-Villigermonooxygenase as enzyme components), a solvent engineering has been carried out identifying isooctane as a suitable co-solvent. Biotransformations in an aqueous-isooctane biphasic solvent system were found to proceed faster at both investigated substrate concentrations of 40 and 80mM, respectively, compared with the analogous enzymatic reactions in pure aqueous medium. In addition, in all cases quantitative conversions were observed after a reaction time of 23 h when using isolated enzymes. The achievements indicate a high compatibility of isooctane [10%(v/v)] with the enzymes as well as the potential for an in situ removal of the organic reaction components, thus decreasing inhibition and/or destabilization effects of these organic components on the enzymes used. In contrast, so far, the use of recombinant whole-cells gave less satisfactory results, whichmight be due to limitations of the permeation of, for example, the substrate through the cell membrane.
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Reimer A, Wedde S, Staudt S, et al. Process Development through Solvent Engineering in the Biocatalytic Synthesis of the Heterocyclic Bulk Chemical epsilon-Caprolactone. JOURNAL OF HETEROCYCLIC CHEMISTRY. 2017;54(1):391-396.
Reimer, A., Wedde, S., Staudt, S., Schmidt, S., Hoeffer, D., Hummel, W., Kragl, U., et al. (2017). Process Development through Solvent Engineering in the Biocatalytic Synthesis of the Heterocyclic Bulk Chemical epsilon-Caprolactone. JOURNAL OF HETEROCYCLIC CHEMISTRY, 54(1), 391-396. doi:10.1002/jhet.2595
Reimer, A., Wedde, S., Staudt, S., Schmidt, S., Hoeffer, D., Hummel, W., Kragl, U., Bornscheuer, U. T., and Gröger, H. (2017). Process Development through Solvent Engineering in the Biocatalytic Synthesis of the Heterocyclic Bulk Chemical epsilon-Caprolactone. JOURNAL OF HETEROCYCLIC CHEMISTRY 54, 391-396.
Reimer, A., et al., 2017. Process Development through Solvent Engineering in the Biocatalytic Synthesis of the Heterocyclic Bulk Chemical epsilon-Caprolactone. JOURNAL OF HETEROCYCLIC CHEMISTRY, 54(1), p 391-396.
A. Reimer, et al., “Process Development through Solvent Engineering in the Biocatalytic Synthesis of the Heterocyclic Bulk Chemical epsilon-Caprolactone”, JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 54, 2017, pp. 391-396.
Reimer, A., Wedde, S., Staudt, S., Schmidt, S., Hoeffer, D., Hummel, W., Kragl, U., Bornscheuer, U.T., Gröger, H.: Process Development through Solvent Engineering in the Biocatalytic Synthesis of the Heterocyclic Bulk Chemical epsilon-Caprolactone. JOURNAL OF HETEROCYCLIC CHEMISTRY. 54, 391-396 (2017).
Reimer, Anna, Wedde, Severin, Staudt, Svenja, Schmidt, Sandy, Hoeffer, Diana, Hummel, Werner, Kragl, Udo, Bornscheuer, Uwe T., and Gröger, Harald. “Process Development through Solvent Engineering in the Biocatalytic Synthesis of the Heterocyclic Bulk Chemical epsilon-Caprolactone”. JOURNAL OF HETEROCYCLIC CHEMISTRY 54.1 (2017): 391-396.
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