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Volume 60, Issue 4
  • ISSN: 2056-5135
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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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2016-01-01
2024-04-25
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References

  1. Hall M., Stueckler C., Ehammer H., Pointner E., Oberdorfer G., Gruber K., Hauer B., Stuermer R., Kroutil W., Macheroux P., and Faber K. Adv. Synth. Catal., 2008, 350, (3), 411 LINK http://dx.doi.org/10.1002/adsc.200700458 [Google Scholar]
  2. Hall M., Stueckler C., Kroutil W., Macheroux P., and Faber K. Angew. Chem. Int. Ed., 2007, 46, (21), 3934 LINK http://dx.doi.org/10.1002/anie.200605168 [Google Scholar]
  3. Chaparro-Riggers J. F., Rogers T. A., Vazquez-Figueroa E., Polizzi K. M., and Bommarius A. S. Adv. Synth. Catal., 2007, 349, (8–9), 1521 LINK http://dx.doi.org/10.1002/adsc.200700074 [Google Scholar]
  4. Müller A., Hauer B., and Rosche B. Biotechnol. Bioeng., 2007, 98, (1), 22 LINK http://dx.doi.org/10.1002/bit.21415 [Google Scholar]
  5. Swiderska M. A., and Stewart J. D. J. Mol. Catal. B: Enzym., 2006, 42, (1–2), 52 LINK http://dx.doi.org/10.1016/j.molcatb.2006.06.023 [Google Scholar]
  6. Warburg O., and Christian W. Naturwissenschaften, 1932, 20, 688 [Google Scholar]
  7. Stott K., Saito K., Thiele D. J., and Massey V. J. Biol. Chem., 1993, 268, 6097 [Google Scholar]
  8. Vaz A. D. N., Chakraborty S., and Massey V. Biochemistry, 1995, 34, (13), 4246 LINK http://dx.doi.org/10.1021/bi00013a014 [Google Scholar]
  9. Williams R. E., and Bruce N. C. Microbiology, 2002, 148, (6), 1607 LINK http://dx.doi.org/10.1099/00221287-148-6-1607 [Google Scholar]
  10. Bougioukou D. J., Walton A. Z., and Stewart J. D. Chem. Commun., 2010, 46, (45), 8558 LINK http://dx.doi.org/10.1039/c0cc03119d [Google Scholar]
  11. Stueckler C., Reiter T. C., Baudendistel N., and Faber K. Tetrahedron, 2010, 66, (3), 663 LINK http://dx.doi.org/10.1016/j.tet.2009.11.065 [Google Scholar]
  12. Bougioukou D. J., Kille S., Taglieber A., and Reetz M. T. Adv. Synth. Catal., 2009, 351, (18), 3287 LINK http://dx.doi.org/10.1002/adsc.200900644 [Google Scholar]
  13. Padhi S. K., Bougioukou D. J., and Stewart J. D. J. Am. Chem. Soc., 2009, 131, (9), 3271 LINK http://dx.doi.org/10.1021/ja8081389 [Google Scholar]
  14. Kosjek B., Fleitz F. J., Dormer P. G., Kuethe J. T., and Devine P. N. Tetrahedron: Asymmetry, 2008, 19, (12), 1403 LINK http://dx.doi.org/10.1016/j.tetasy.2008.05.023 [Google Scholar]
  15. Stueckler C., Hall M., Ehammer H., Pointner E., Kroutil W., Macheroux P., and Faber K. Org. Lett., 2007, 9, (26), 5409 LINK http://dx.doi.org/10.1021/ol7019185 [Google Scholar]
  16. Chaparro-Riggers J. F., Rogers T. A., Vazquez-Figueroa E., Polizzi K. M., and Bommarius A. S. Adv. Synth. Catal., 2007, 349, (8–9), 1521 LINK http://dx.doi.org/10.1002/adsc.20070007 [Google Scholar]
  17. Kataoka M., Kotaka A., Thiwthong R., Wada M., Nakamori S., and Shimizu S. J. Biotechnol., 2004, 114, (1–2), 1 LINK http://dx.doi.org/10.1016/j.jbiotec.2004.04.033 [Google Scholar]
  18. Mangan D., Miskelly I., and Moody T. S. Adv. Synth. Catal., 2012, 354, (11–12), 2185 LINK http://dx.doi.org/10.1002/adsc.201101006 [Google Scholar]
  19. Bechtold M., Brenna E., Femmer C., Gatti F. G., Panke S., Parmeggiani F., and Sacchetti A. Org. Process Res. Dev., 2012, 16, (2), 269 LINK http://dx.doi.org/10.1021/op200085k [Google Scholar]
  20. Savile C. K., Mitchell V., Zhang X., and Huisman G. W. Codexis Inc, ‘Enone Reductases’, US Patent Appl . 2015/0,315,613 [Google Scholar]
  21. Iqbal N., Rudroff F., Brigé A., Van Beeumen J., and Mihovilovic M. D. Tetrahedron, 2012, 68, (37), 7619 LINK http://dx.doi.org/10.1016/j.tet.2012.05.092 [Google Scholar]
  22. Yanto Y., Winkler C. K., Lohr S., Hall M., Faber K., and Bommarius A. S. Org. Lett., 2011, 13, (10), 2540 LINK http://dx.doi.org/10.1021/ol200394p [Google Scholar]
  23. Hall M., Stueckler C., Hauer B., Stuermer R., Friedrich T., Breuer M., Kroutil W., and Faber K. Eur. J. Org. Chem., 2008, (9), 1511 LINK http://dx.doi.org/10.1002/ejoc.200701208 [Google Scholar]
  24. Chaplin M. F., and Bucke C. “Enzyme Technology”, Cambridge University Press, Cambridge, UK, 1990 [Google Scholar]
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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
/content/journals/10.1595/205651316X692572
/content/journals/10.1595/205651316X692572
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  • Article Type: Research Article

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