Reduction of Activated Carbon-Carbon Double Bonds using Highly Active and Enantioselective Double Bond Reductases: ENEs from Johnson Matthey’s enzyme collection provide a suitable alternative to metal-catalysed hydrogenation

By Beatriz Domínguez; Ursula Schell; Serena Bisagni; Thomas Kalthoff

doi:10.1595/205651316X692572

ISSN: 2056-5135

oa Reduction of Activated Carbon-Carbon Double Bonds using Highly Active and Enantioselective Double Bond Reductases

ENEs from Johnson Matthey’s enzyme collection provide a suitable alternative to metal-catalysed hydrogenation
Authors: By Beatriz Domínguez¹, Ursula Schell¹, Serena Bisagni¹ and Thomas Kalthoff¹
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Affiliations: ¹ Johnson Matthey Catalysis and Chiral Technologies, 260 Cambridge Science Park, Milton Road, Cambridge, CB4 0WEUK
Source: Johnson Matthey Technology Review, Volume 60, Issue 4, Oct 2016, p. 243 - 249
DOI: https://doi.org/10.1595/205651316X692572
- Published online: 01 Jan 2016

Abstract

The use of enzymes for the asymmetric reduction of activated C=C double bonds is a viable and straightforward alternative to chiral hydrogenation. The number of isolated and characterised double bond reductases (ENEs) has grown significantly over the past fifteen years and the use of this enzyme class in organic synthesis has increased accordingly. In this article we examine the ENE-catalysed reduction of a number of activated alkenes using enzymes from Johnson Matthey’s collection. These reductions proved to be scalable: they can be run at high substrate concentration, delivering the reduced product in high yield and high chemical purity.

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References

M. Hall, C. Stueckler, H. Ehammer, E. Pointner, G. Oberdorfer, K. Gruber, B. Hauer, R. Stuermer, W. Kroutil, P. Macheroux, K. Faber, Adv. Synth. Catal., 2008, 350, (3), 411 LINK http://dx.doi.org/10.1002/adsc.200700458 [Google Scholar]
M. Hall, C. Stueckler, W. Kroutil, P. Macheroux, K. Faber, Angew. Chem. Int. Ed., 2007, 46, (21), 3934 LINK http://dx.doi.org/10.1002/anie.200605168 [Google Scholar]
J. F. Chaparro-Riggers, T. A. Rogers, E. Vazquez-Figueroa, K. M. Polizzi, A. S. Bommarius, Adv. Synth. Catal., 2007, 349, (8–9), 1521 LINK http://dx.doi.org/10.1002/adsc.200700074 [Google Scholar]
A. Müller, B. Hauer, B. Rosche, Biotechnol. Bioeng., 2007, 98, (1), 22 LINK http://dx.doi.org/10.1002/bit.21415 [Google Scholar]
M. A. Swiderska, J. D. Stewart, J. Mol. Catal. B: Enzym., 2006, 42, (1–2), 52 LINK http://dx.doi.org/10.1016/j.molcatb.2006.06.023 [Google Scholar]
O. Warburg, W. Christian, Naturwissenschaften, 1932, 20, 688 [Google Scholar]
K. Stott, K. Saito, D. J. Thiele, V. Massey, J. Biol. Chem., 1993, 268, 6097 [Google Scholar]
A. D. N. Vaz, S. Chakraborty, V. Massey, Biochemistry, 1995, 34, (13), 4246 LINK http://dx.doi.org/10.1021/bi00013a014 [Google Scholar]
R. E. Williams, N. C. Bruce, Microbiology, 2002, 148, (6), 1607 LINK http://dx.doi.org/10.1099/00221287-148-6-1607 [Google Scholar]
D. J. Bougioukou, A. Z. Walton, J. D. Stewart, Chem. Commun., 2010, 46, (45), 8558 LINK http://dx.doi.org/10.1039/c0cc03119d [Google Scholar]
C. Stueckler, T. C. Reiter, N. Baudendistel, K. Faber, Tetrahedron, 2010, 66, (3), 663 LINK http://dx.doi.org/10.1016/j.tet.2009.11.065 [Google Scholar]
D. J. Bougioukou, S. Kille, A. Taglieber, M. T. Reetz, Adv. Synth. Catal., 2009, 351, (18), 3287 LINK http://dx.doi.org/10.1002/adsc.200900644 [Google Scholar]
S. K. Padhi, D. J. Bougioukou, J. D. Stewart, J. Am. Chem. Soc., 2009, 131, (9), 3271 LINK http://dx.doi.org/10.1021/ja8081389 [Google Scholar]
B. Kosjek, F. J. Fleitz, P. G. Dormer, J. T. Kuethe, P. N. Devine, Tetrahedron: Asymmetry, 2008, 19, (12), 1403 LINK http://dx.doi.org/10.1016/j.tetasy.2008.05.023 [Google Scholar]
C. Stueckler, M. Hall, H. Ehammer, E. Pointner, W. Kroutil, P. Macheroux, K. Faber, Org. Lett., 2007, 9, (26), 5409 LINK http://dx.doi.org/10.1021/ol7019185 [Google Scholar]
J. F. Chaparro-Riggers, T. A. Rogers, E. Vazquez-Figueroa, K. M. Polizzi, A. S. Bommarius, Adv. Synth. Catal., 2007, 349, (8–9), 1521 LINK http://dx.doi.org/10.1002/adsc.20070007 [Google Scholar]
M. Kataoka, A. Kotaka, R. Thiwthong, M. Wada, S. Nakamori, S. Shimizu, J. Biotechnol., 2004, 114, (1–2), 1 LINK http://dx.doi.org/10.1016/j.jbiotec.2004.04.033 [Google Scholar]
D. Mangan, I. Miskelly, T. S. Moody, Adv. Synth. Catal., 2012, 354, (11–12), 2185 LINK http://dx.doi.org/10.1002/adsc.201101006 [Google Scholar]
M. Bechtold, E. Brenna, C. Femmer, F. G. Gatti, S. Panke, F. Parmeggiani, A. Sacchetti, Org. Process Res. Dev., 2012, 16, (2), 269 LINK http://dx.doi.org/10.1021/op200085k [Google Scholar]
C. K. Savile, V. Mitchell, X. Zhang, G. W. Huisman, Codexis Inc,, ‘Enone Reductases’, US Patent Appl . 2015/0,315,613 [Google Scholar]
N. Iqbal, F. Rudroff, A. Brigé, J. Van Beeumen, M. D. Mihovilovic, Tetrahedron, 2012, 68, (37), 7619 LINK http://dx.doi.org/10.1016/j.tet.2012.05.092 [Google Scholar]
Y. Yanto, C. K. Winkler, S. Lohr, M. Hall, K. Faber, A. S. Bommarius, Org. Lett., 2011, 13, (10), 2540 LINK http://dx.doi.org/10.1021/ol200394p [Google Scholar]
M. Hall, C. Stueckler, B. Hauer, R. Stuermer, T. Friedrich, M. Breuer, W. Kroutil, K. Faber, Eur. J. Org. Chem., 2008, (9), 1511 LINK http://dx.doi.org/10.1002/ejoc.200701208 [Google Scholar]
M. F. Chaplin, C. Bucke, “Enzyme Technology”, Cambridge University Press, Cambridge, UK, 1990 [Google Scholar]

/content/journals/10.1595/205651316X692572

Reduction of Activated Carbon-Carbon Double Bonds using Highly Active and Enantioselective Double Bond Reductases

Johnson Matthey Technology Review 60, 243 (2016); https://doi.org/10.1595/205651316X692572

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Abstract

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