Low-temperature enzymatic hydrolysis resolution in mini-emulsion media

• Published in: Chemical Papers
• Main Authors: Lourenço, Nuno M. T., Matias, Sara C., Altas, Margarida C., Fonseca, Luis P.
• Format: Article in Journal/Newspaper
• Language: unknown
• Published: Springer Science and Business Media LLC 2015
• Subjects: Materials Chemistry; Industrial and Manufacturing Engineering; General Chemical Engineering; Biochemistry; General Chemistry; Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1515/chempap-2015-0032

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 %.