Bicontinuous Microemulsion as Reaction Medium for ω-Transaminase Catalysed Biotransformations

M. Laupheimer; S. Engelskirchen; K. Tauber; W. Kroutil; C. Stubenrauch

doi:10.3139/113.110100

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Bicontinuous Microemulsion as Reaction Medium for ω-Transaminase Catalysed Biotransformations

M. Laupheimer , S. Engelskirchen , K. Tauber , W. Kroutil und C. Stubenrauch

Veröffentlicht/Copyright: 5. April 2013

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Abstract

Due to their high enantioselectivity biotransformations, i.e. enzyme-catalysed conversion of organic compounds, are extremely attractive reactions. However, a limiting factor for choosing substrates is the enzyme-substrate incompatibility. This occurs when a hydrophilic enzyme which naturally resides in the aqueous cell cytoplasm is supposed to convert a hydrophobic substrate. In this context bicontinuous microemulsions appear to be a beneficial reaction medium for biotransformations, particularly due to their large interfacial area between a hydrophilic and a hydrophobic compound. As a “proof of concept” we performed ω-transaminase (EC 2.6.1.18) catalysed model reactions in a bicontinuous microemulsion of the type phosphate buffer/NaCl – n-octane – pentaethylene glycol monodecyl ether.

Kurzfassung

Biotransformationen, also Enzym-katalysierte Umsetzungen organischer Substanzen, sind besonders dank ihrer hohen Enantioselektivität äußerst attraktive Reaktionen. Ein limitierender Faktor bei der Substratauswahl ist die Enzym-Substrat-Inkompatibilität. Diese tritt auf, wenn durch hydrophile Enzyme, die sich im wässrigen Zellzytoplasma befinden, hydrophobe Substrate umgesetzt werden sollen. Insbesondere aufgrund ihrer großen Grenzfläche zwischen einer hydrophilen und einer hydrophoben Komponente scheinen bikontinuierliche Mikroemulsionen ein besonders günstiges Reaktionsmedium für solche Biotransformationen darzustellen. Um dies zu zeigen, wurden ω-Transaminase (EC 2.6.1.18)-katalysierte kinetische Modellreaktionen in einer Mikroemulsion vom Typ Phosphatpufferlösung/NaCl – n-Oktan – Pentaethylenglycolmonodecylether durchgeführt.

Key words:: Bicontinuous microemulsion; biotransformation; enzyme reaction; enzyme-substrate incompatibility; reaction medium

Stichwörter:: Bikontinuierliche Mikroemulsionen; Biotransformation; Enzymreaktionen; Enzym-Substrat-Inkompatibilität; Reaktionsmedium

^∗ Dr. Sandra Engelskirchen, Universität Stuttgart, Institut für Physikalische Chemie, Pfaffenwaldring 55, 70569 Stuttgart, Germany, Tel.: +49(0)711/68564494, Fax: +49(0)711/68564443. E-Mail: sandra.engelskirchen@ipc.uni-stuttgart.de

Dipl.-Chem. Michaela Laupheimer studied chemistry at the University of Stuttgart (Germany). She did a six-month internship at the Robert Bosch LLC Research and Technology Center in Palo Alto (USA) from August 2008 to January 2009 and received her diploma in March 2010. Since then she is working on her PhD thesis at the Institute of Physical Chemistry at the University of Stuttgart.

Dr. Sandra Engelskirchen studied chemistry at the University of Cologne (Germany) and received her PhD in 2005. Subsequently she worked for one year as a laboratory manager at Elastogran GmbH, Lemförde (Germany). In 2006 she went back to the University of Cologne as a researcher and lecturer in the Institute of Physical Chemistry. From 2007 to 2009 she had a postdoctoral position at the Karl-Franzens Universität Graz (Austria) and since 2009 she has been working as researcher and lecturer at the Institute of Physical Chemistry at the University of Stuttgart (Germany).

Mag. Katharina Tauber studied chemistry at the University of Graz (Austria) finishing her diploma in 2009. Since September 2009 she is working on her PhD thesis at the Department of Chemistry at the University of Graz (Austria).

Prof. Dr. Wolfgang Kroutil studied technical mathematics and technical chemistry at the University of Technology in Graz (Austria) from where he also received his PhD in Chemistry in 1998. From 1998 to 1999 he did a postdoctoral year at Syngenta (formerly Novartis Crop Protection AG) in Basel (Switzerland) after which he became R&D manager at Krems Chemie Chemical Services GmbH (Austria). From 2000 to 2004 he worked as assistant professor at the Department of Chemistry at the University of Graz (Austria). After his habilitation he became an associate professor in 2004 at the University of Graz (Austria).

Prof. Dr. Cosima Stubenrauch studied chemistry at the universities of Münster and Freiburg and received her PhD in Physical Chemistry at the TU Berlin in 1997. After a postdoctoral year at the Université Paris Sud, she worked as an associate researcher and lecturer at the Institute of Physical Chemistry, University of Cologne, from 1999 to 2004. From 2005 to 2009 she worked as lecturer, senior lecturer and associate professor at University College Dublin, where she holds a visiting professorship since 2009. Also since 2009 she is professor and head of chair “Physical Chemistry of Condensed Matter” at the University of Stuttgart (Germany). Furthermore, since 2010 she is docent in Physical Chemistry in Thin Films at the KTH Royal Institute of Technology, Stockholm (Sweden).

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Received: 2010-08-03

Published Online: 2013-04-05

Published in Print: 2011-01-01

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https://doi.org/10.3139/113.110100

Schlagwörter für diesen Artikel

Bicontinuous microemulsion; biotransformation; enzyme reaction; enzyme-substrate incompatibility; reaction medium