can be tuned by changing the reaction medium. The efficient
production of both enantiomers of optically active alcohols is
of great interest as they are building blocks for the synthesis of
pharmaceutically important molecules.
6 H. Gro¨ger, W. Hummel, S. Buchholz, K. Drauz, T. V. Nguyen, C.
Rollmann, H. Hu¨sken and K. Abokitse, Org. Lett., 2003, 5, 173–176.
7 G. D. Gonzalo, I. Lavandera, K. Faber and W. Kroutil, Org. Lett.,
2007, 9, 2163–2166.
8 (a) T. Itoh, Y. Matsushita, Y. Abe, S. Han, S. Wada, S. Hayase, M.
Kawatsura, S. Takai, M. Morimoto and Y. Hirose, Chem.–Eur. J., 2006,
12, 9228–9237; (b) K. W. Kim, B. Song, M. Y. Choi and M. J. Kim,
Org. Lett., 2001, 3, 1507–1509.
9 (a) D. C. Burdette and J. G. Zeikus, Biochem.J., 1994, 302, 163–170;
(b) D. C. Burdette, C. Vieille and J. G. Zeikus, Biochem. J., 1996, 316,
115–122.
10 (a) V. T. Pham and R. S. Phillips, J. Am. Chem. Soc., 1990, 112, 3629–
3632; (b) V. T. Pham, R. S. Phillips and L. G. Ljungdahl, J. Am. Chem.
Soc., 1989, 111, 1935–1936.
Acknowledgements
Financial support from National Science Foundation (Grant num-
ber 0445511) to RSP, JGZ, and CV is gratefully acknowledged. We
thank Prof. Peter Schreiner and Dr Derek Wolfe for the generous
gift of [bmim][BF4].
11 (a) C. Heiss, M. Laivenieks, J. G. Zeikus and R. S. Phillips, Bioorg. Med.
Chem., 2001, 9, 1659–1666; (b) C. Heiss and R. S. Phillips, J. Chem.
Soc., Perkin Trans. 1, 2000, 2821–2825.
12 K. I. Ziegelmann-Fjeld, M. M. Musa, R. S. Phillips, J. G. Zeikus and
C. Vieille, Protein Eng. Des. Sel., 2007, 20, 47–55.
13 M. M. Musa, K. I. Ziegelmann-Fjeld, C. Vieille, J. G. Zeikus and R. S.
Phillips, J. Org. Chem., 2007, 72, 30–34.
14 V. Prelog, Pure Appl. Chem., 1964, 9, 119–130.
15 M. M. Musa, K. I. Ziegelmann-Fjeld, C. Vieille, J. G. Zeikus and R. S.
Phillips, Angew. Chem., Int. Ed., 2007, 46, 3091–3094.
16 (a) B. Kosjek, W. Stampfer, M. Pogorevc, W. Goessler, K. Faber and
W. Kroutil, Biotechnol. Bioeng., 2004, 86, 55–62; (b) B. Kosjek, W.
Stampfer, S. M. Glueck, M. Pogorevc, U. Ellmer, S. R. Wallner, M. F.
Koegl, T. M. Poessl, S. F. Mayer, B. Ueberbacher, K. Faber and W.
Kroutil, J. Mol. Catal. B, 2003, 22, 1–6.
17 H. D. Simpson and D. A. Cowan, Protein Peptide Lett., 1997, 4, 25–32.
18 (a) R. S. Phillips, J. Mol. Catal. B, 2002, 19–20, 103–107; (b) C. Heiss,
M. Laivenieks, J. G. Zeikus and R. S. Phillips, J. Am. Chem. Soc., 2001,
123, 345–346.
References
1 (a) K. Faber, Biotransformation in organic chemistry, 5th ed., Springer-
Verlag, New York, 2004; (b) R. N. Patel, Biocatalysis in the pharma-
ceutical and biotechnology industries, CRC Press LLC, Boca Raton,
Florida, 2007.
2 (a) A. M. Klibanov, Curr. Opin. Biotechnol., 2003, 14, 427–431;
(b) A. M. Klibanov, Nature, 2001, 409, 241–246; (c) G. Carrea and
S. Riva, Angew. Chem., Int. Ed., 2000, 39, 2226–2254.
3 (a) K. Schroer, E. Tacha and S. Lutz, Org. Process Res. Dev., 2007,
11, 836–841; (b) T. Matsuda, Y. Yamagishi, S. Koguchi, N. Iwai and T.
Kitazume, Tetrahedron Lett., 2006, 47, 4619–4622; (c) Z. Yang and W.
Pan, Enzyme Microb. Technol., 2005, 37, 19–28; (d) M. Eckstein, M.
Villela, A. Liese and U. Kragl, Chem. Commun., 2004, 1084–1085; (e) S.
Park and R. J. Kazlauskas, Curr. Opin. Biotechnol., 2003, 14, 432–437.
4 (a) N. Blanchard and P. Weghe, Org. Biomol. Chem., 2006, 4, 2348–
2353; (b) T. Daußmann, T. C. Rosen and P. Du¨nkelmann, Eng. Life
Sci., 2006, 6, 125–129; (c) E. Garcia-Urdiales, I. Alfonso and V. Gotor,
Chem. Rev., 2005, 105, 313–354; (d) W. Kroutil, H. Mang, K. Edeger
and K. Faber, Curr. Opin. Chem. Biol., 2004, 8, 120–126.
19 B. Mart´ın-Matute and J. E. Ba¨ckvall, Curr. Opin. Chem. Biol., 2007,
11, 226–232.
20 M. Villela Filho, T. Stillger, M. Muller, A. Liese and C. Wandrey,
Angew. Chem., Int. Ed., 2003, 42, 2993–2996.
21 J. A. King and F. H. McMillan, J. Am. Chem. Soc., 1951, 73, 4911–4915.
22 A. Ghanem and V. Schuring, Tetrahedron: Asymmetry, 2003, 14, 57–62.
23 D. M. Wolfe and P. R. Schreiner, Eur. J. Org. Chem., 2007, 2825–2838.
24 C. Thomazeau, H. Olivier-Bourbigou, L. Magna, S. Luts and B.
Gilbert, J. Am. Chem. Soc., 2003, 125, 5264–5265.
5 (a) J. Zhang, B. Witholt and Z. Li, Adv. Synth. Catal., 2006, 348, 429–
433; (b) K. Edegger, W. Stampfer, B. Seisser, K. Faber, S. F. Mayer,
R. Oehrlein, A. Hafner and W. Kroutil, Eur. J. Org. Chem., 2006,
1904–1909; (c) D. Zhu, Y. Yang and L. Hua, J. Org. Chem., 2006, 71,
4202–4205; (d) H. Gro¨ger, F. Chamouleau, N. Orologas, C. Rollmann,
K. Drauz, W. Hummel, A. Weckbecker and O. May, Angew. Chem., Int.
Ed., 2006, 45, 5677–5681; (e) R. L. Hanson, S. Goldberg, A. Goswami,
T. P. Tully and R. N. Patel, Adv. Synth. Catal., 2005, 347, 1073–
1080.
25 C. S. Chen, Y. Fujimoto, G. Girdaukas and C. J. Sih, J. Am. Chem.
Soc., 1982, 104, 7294–7299.
892 | Org. Biomol. Chem., 2008, 6, 887–892
This journal is
The Royal Society of Chemistry 2008
©