ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Low-temperature enzymatic hydrolysis resolution in mini-emulsion media

Nuno M. T. Lourenço, Sara C. Matias, Margarida C. Altas, and Luis P. Fonseca

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

E-mail: nmtl@tecnico.ulisboa.pt

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 %.

Keywords: mini-emulsion – enzymatic kinetic resolution – secondary alcohols – low temperature

Full paper is available at www.springerlink.com.

DOI: 10.1515/chempap-2015-0032

Chemical Papers 69 (6) 810–816 (2015)