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Enzymatic Production of Both Enantiomers of Rhododendrol
Corresponding Author(s) : Musa M. Musa
Asian Journal of Chemistry,
Vol. 26 No. 20 (2014)
Abstract
An asymmetric synthetic approach to produce (R)- and (S)-rhododendrol is described. W110A Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase (W110A TeSADH), an (S)-specific mutant of TeSADH, is used in this approach. The enantioselective reduction of 4-(4'-hydroxyphenyl)-2-butanone catalyzed by W110A TeSADH yielded (S)-rhododendrol, the Prelog product. The anti-Prelog product, (R)-rhododendrol, is produced from (rac)-rhododendrol through enantiospecific kinetic resolution catalyzed by W110A TeSADH.
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- K. Archangelsky, Arch. Exp. Path. Pharm, 46, 313 (1901).
- W.H. Tallent, J. Org. Chem., 29, 988 (1964).
- M.H. Kim, A. Nugroho, J. Choi, J.H. Park and H.J. Park, Arch. Pharm. Res., 34, 971 (2011).
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- U.T. Bornscheuer, G.W. Huisman, R.J. Kazlauskas, S. Lutz, J.C. Moore and K. Robins, Nature, 485, 185 (2012).
- F. Hollmann, I.W.C.E. Arends and D. Holtmann, Green Chem., 13, 2285 (2011).
- M. Hall and A.S. Bommarius, Chem. Rev., 111, 4088 (2011).
- D.S. Burdette and J.G. Zeikus, Biochem. J., 302, 163 (1994).
- D.S. Burdette, V.V. Tchernajencko and J.G. Zeikus, Enzyme Microb. Technol., 27, 11 (2000).
- M.M. Musa, K.I. Ziegelmann-Fjeld, C. Vieille and R.S. Phillips, Org. Biomol. Chem., 6, 887 (2008).
- K.I. Ziegelmann-Fjeld, M.M. Musa, R.S. Phillips, J.G. Zeikus and C. Vieille, Protein Eng. Des. Sel., 20, 47 (2007).
- V. Prelog, Pure Appl. Chem., 9, 119 (1964).
- M.M. Musa, R.S. Phillips, M. Laivenieks, C. Vieille, M. Takahashi and S.M. Hamdan, Org. Biomol. Chem., 11, 2911 (2013).
- A. Ghanem and V. Schurig, Tetrahedron Asymmetry, 14, 57 (2003).
- W. Kroutil, H. Mang, K. Edegger and K. Faber, Curr. Opin. Chem. Biol., 8, 120 (2004).
- M.M. Musa and R.S. Phillips, Catal. Sci. Technol., 1, 1311 (2011).
- M.M. Musa, K.I. Ziegelmann-Fjeld, C. Vieille, J.G. Zeikus and R.S. Phillips, J. Org. Chem., 72, 30 (2007).
References
K. Archangelsky, Arch. Exp. Path. Pharm, 46, 313 (1901).
W.H. Tallent, J. Org. Chem., 29, 988 (1964).
M.H. Kim, A. Nugroho, J. Choi, J.H. Park and H.J. Park, Arch. Pharm. Res., 34, 971 (2011).
(a) G. Sabitha, B. Thirupathaiah and J. Yadav, Synth. Commun., 37, 1683 (2007).; (b) Y. Yuasa, S. Shibuya and Y. Yuasa, Synth. Commun., 33, 1469 (2003).; (c) B. Das, S. Padma Rao, K.V.N.S. Srinivas and J.S. Yadav, Phytochemistry, 33, 1529 (1993).; (d) T. Kitayama, S. Isomori and K. Nakamura, Tetrahedron Asymmetry, 24, 621 (2013).
U.T. Bornscheuer, G.W. Huisman, R.J. Kazlauskas, S. Lutz, J.C. Moore and K. Robins, Nature, 485, 185 (2012).
F. Hollmann, I.W.C.E. Arends and D. Holtmann, Green Chem., 13, 2285 (2011).
M. Hall and A.S. Bommarius, Chem. Rev., 111, 4088 (2011).
D.S. Burdette and J.G. Zeikus, Biochem. J., 302, 163 (1994).
D.S. Burdette, V.V. Tchernajencko and J.G. Zeikus, Enzyme Microb. Technol., 27, 11 (2000).
M.M. Musa, K.I. Ziegelmann-Fjeld, C. Vieille and R.S. Phillips, Org. Biomol. Chem., 6, 887 (2008).
K.I. Ziegelmann-Fjeld, M.M. Musa, R.S. Phillips, J.G. Zeikus and C. Vieille, Protein Eng. Des. Sel., 20, 47 (2007).
V. Prelog, Pure Appl. Chem., 9, 119 (1964).
M.M. Musa, R.S. Phillips, M. Laivenieks, C. Vieille, M. Takahashi and S.M. Hamdan, Org. Biomol. Chem., 11, 2911 (2013).
A. Ghanem and V. Schurig, Tetrahedron Asymmetry, 14, 57 (2003).
W. Kroutil, H. Mang, K. Edegger and K. Faber, Curr. Opin. Chem. Biol., 8, 120 (2004).
M.M. Musa and R.S. Phillips, Catal. Sci. Technol., 1, 1311 (2011).
M.M. Musa, K.I. Ziegelmann-Fjeld, C. Vieille, J.G. Zeikus and R.S. Phillips, J. Org. Chem., 72, 30 (2007).