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Low-temperature enzymatic hydrolysis resolution in mini-emulsion media

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Abstract

A low-temperature mini-emulsion medium for the enzymatic resolution of 1-phenylethanol is described for the first time. The enzymatic hydrolysis resolution of 1-phenylethyl esters with different chain-lengths in the presence of Candida antarctica lipase B in mini-emulsion media was shown to be significantly controlled by temperature. In this system, the direct effect of temperature on the mini-emulsion size was observed. For the longer 1-phenylethyl ester, 1-phenylethyl dodecanoate, the enzymatic resolution was promoted exclusively at low temperatures. The preparative mini-emulsion enzymatic reaction of 1-phenylethyl dodecanoate at 4 °C afforded the isolation of (R)-phenylethanol with a yield of 36 % with an ee of 99 %. (S)-Phenylethanol was isolated with a 51 % yield with an ee of 79 %.

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Authors and Affiliations

  1. Centre for Biological and Chemical Engineering, IBB - Institute for Biotechnology and Bioengineering, Av. Rovisco Pais, 1, 1049-001, Lisboa, Portugal

    Nuno M. T. Lourenço & Luis P. Fonseca

  2. Department of Bioengineering, Instituto Superior Técnico, Av. Rovisco Pais, 1, 1049-001, Lisboa, Portugal

    Sara C. Matias, Margarida C. Altas & Luis P. Fonseca

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  1. Nuno M. T. Lourenço
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  2. Sara C. Matias
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  3. Margarida C. Altas
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  4. Luis P. Fonseca
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Correspondence to Nuno M. T. Lourenço.

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Lourenço, N.M.T., Matias, S.C., Altas, M.C. et al. Low-temperature enzymatic hydrolysis resolution in mini-emulsion media. Chem. Pap. 69, 810–816 (2015). https://doi.org/10.1515/chempap-2015-0032

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  • DOI: https://doi.org/10.1515/chempap-2015-0032

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