Advertisement

Stereoselective Reduction of Prochiral Cyclic 1,3-Diketones Using Different Biocatalysts

  • Martina Letizia Contente
  • Federica Dall’Oglio
  • Francesca Annunziata
  • Francesco Molinari
  • Marco Rabuffetti
  • Diego Romano
  • Lucia Tamborini
  • Dörte Rother
  • Andrea PintoEmail author
Article
  • 13 Downloads

Abstract

We have developed biocatalytic methods for the stereoselective reduction of cyclic prochiral 1,3-diketones for the production of optically active β-hydroxyketones and/or 1,3-diols. The recombinant ketoreductase KRED1-Pglu (formulated as purified catalyst) and whole cells of wild type Escherichia coli DE3 Star were used as biocatalysts, displaying different and sometimes complementary stereoselectivity, thus allowing the preparation of stereochemically pure β-hydroxyketones (12–66% isolated yields, > 99% e.e.) and 1,3-diols (40–60% isolated yields, > 99% e.e.).

Graphic Abstract

Keywords

Biocatalytic reduction 1-3 diketones β-hydroxyketones 1,3-Diols Enzymatic Whole cells 

Notes

Acknowledgements

The authors thank the University of Milan for funding the stay of Federica Dall’Oglio at the Biotechnology Forschungszentrum of Jülich.

Compliance with Ethical Standards

Conflict of interest

The authors declare no conflict of interest.

Supplementary material

10562_2019_3015_MOESM1_ESM.docx (140 kb)
Electronic supplementary material 1 (DOCX 140 kb)

References

  1. 1.
    Nakamura K, Matsuda T (2006) Curr Org Chem 10:1217–1246CrossRefGoogle Scholar
  2. 2.
    Hoyos P, Sinisterra JV, Molinari F, Alcantara AR, Dominguez de Maria P (2010) Acc Chem Res 43:288–299CrossRefGoogle Scholar
  3. 3.
    Sehl T, Hailes HC, Ward JM, Menyes U, Pohl M, Rother D (2014) Green Chem 16:3341–3348CrossRefGoogle Scholar
  4. 4.
    Chen Y, Chen C, Wu X (2012) Chem Soc Rev 41:1742–1753CrossRefGoogle Scholar
  5. 5.
    Kalaitzakis D, Rozzell JD, Smonou I, Kambourakis S (2006) Adv Synth Catal 348:1958–1969CrossRefGoogle Scholar
  6. 6.
    Kalaitzakis D, Smonou I (2010) J Org Chem 75:8658–8661CrossRefGoogle Scholar
  7. 7.
    Bataille CJR, Donohoe TJ (2011) Chem Soc Rev 40:114–128CrossRefGoogle Scholar
  8. 8.
    Nguyen TN, Chen PA, Setthakarn K, May JA (2018) Molecules 23:2317CrossRefGoogle Scholar
  9. 9.
    Paterson I, Chen DYK, Acena JL, Franklin AS (2000) Org Lett 2:1513–1516CrossRefGoogle Scholar
  10. 10.
    Mukai K, Urabe D, Kasura S, Aoki N, Inoue MA (2013) Angew Chem Int Ed 52:5300–5304CrossRefGoogle Scholar
  11. 11.
    Urabe D, Nakagawa Y, Mukai K, Fukushima K, Aoki N, Itoh H, Nagatomo M, Inoue M (2018) J Org Chem 83:13888–13910CrossRefGoogle Scholar
  12. 12.
    Haberland J, Kriegesmann A, Wolfram E, Hummel W, Liese A (2002) Appl Microbiol Biotechnol 58:595–599CrossRefGoogle Scholar
  13. 13.
    Grau BT, Devine PN, Di Michele LN, Kosjek B (2007) Org Lett 9:4951–4954CrossRefGoogle Scholar
  14. 14.
    Lüdeke S, Richter M, Müller M (2009) Adv Synth Catal 351:253–259CrossRefGoogle Scholar
  15. 15.
    Kurina-Sanz M, Bisogno FR, Lavandera I, Orden AA, Gotor V (2009) Adv Synth Catal 351:1842–1848CrossRefGoogle Scholar
  16. 16.
    Husain SH, Stillger T, Dünkelmann P, Lödige M, Walter L, Breitling E, Pohl M, Bürchner M, Krossing I, Müller M, Romano D, Molinari F (2011) Adv Synth Catal 353:2359–2362CrossRefGoogle Scholar
  17. 17.
    Mourelle-Insua A, de Gonzalo G, Lavandera I, Gotor-Fernández V (2018) Catalysts 8:150CrossRefGoogle Scholar
  18. 18.
    Brooks W, Mazdiyasni M, Grothaus PG (1987) J Org Chem 52:3223–3232CrossRefGoogle Scholar
  19. 19.
    Watanabe W, Iwamoto M, Nakada M (2005) J Org Chem 70:4652–4658CrossRefGoogle Scholar
  20. 20.
    Kosmol H, Kieslich K, Vossing R, Koch HJ, Petzoldt K, Gibian H (1967) Justus Liebigs Ann Chem 701:199–205CrossRefGoogle Scholar
  21. 21.
    Contente ML, Molinari F, Serra I, Pinto A, Romano D (2016) Eur J Org Chem 2016:1260–1263CrossRefGoogle Scholar
  22. 22.
    Contente ML, Serra I, Brambilla M, Eberini I, Gianazza E, De Vitis V, Molinari F, Zambelli P, Romano D (2016) Appl Microbiol Biotechnol 100:193–201CrossRefGoogle Scholar
  23. 23.
    Contente ML, Serra I, Molinari F, Gandolfi R, Pinto A, Romano D (2016) Tetrahedron 72:3974–3979CrossRefGoogle Scholar
  24. 24.
    Contente ML, Molinari F, Zambelli P, De Vitis V, Gandolfi R, Pinto A, Romano D (2014) Tetrahedron Lett 55:7051–7053CrossRefGoogle Scholar
  25. 25.
    Contente ML, Zambelli P, Galafassi S, Tamborini L, Pinto A, Conti P, Molinari F, Romano D (2015) J Mol Catal B 114:7–12CrossRefGoogle Scholar
  26. 26.
    Contente ML, Serra I, Palazzolo L, Parravicini C, Gianazza E, Eberini I, Pinto A, Molinari F, Guidi B, Romano D (2016) Org Biomol Chem 14:3404–3408CrossRefGoogle Scholar
  27. 27.
    Dall’Oglio F, Contente ML, Conti P, Molinari F, Monfredi D, Pinto A, Romano D, Ubiali D, Tamborini L (2017) Catal Commun 93:29–32CrossRefGoogle Scholar
  28. 28.
    Manna MS, Mukherjee S (2014) Chem Sci 5:1627–1633CrossRefGoogle Scholar
  29. 29.
    Byrne SJ, Fletcher AJ, Hebeisen P, Willis MC (2010) Org Biomol Chem 8:758–760CrossRefGoogle Scholar
  30. 30.
    Oeggl R, Neumann T, Gätgens J, Romano D, Noack S, Rother D (2018) Front Bioeng Biotechnol 6:196CrossRefGoogle Scholar
  31. 31.
    Yeung YY, Chein RJ, Corey EJ (2007) J Am Chem Soc 129:10346–10347CrossRefGoogle Scholar
  32. 32.
    Kolakowski RV, Manpadi M, Zhang Y, Emge TJ, Williams LJ (2009) J Am Chem Soc 131:12910–12911CrossRefGoogle Scholar
  33. 33.
    Salter GJ, Kell DB (1995) Crit Rev Biotechnol 15:139–177CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Martina Letizia Contente
    • 1
    • 3
  • Federica Dall’Oglio
    • 2
  • Francesca Annunziata
    • 2
  • Francesco Molinari
    • 3
  • Marco Rabuffetti
    • 3
  • Diego Romano
    • 3
  • Lucia Tamborini
    • 2
  • Dörte Rother
    • 4
  • Andrea Pinto
    • 3
    Email author
  1. 1.School of ChemistryUniversity of Nottingham, University ParkNottinghamUK
  2. 2.Department of Pharmaceutical Sciences (DISFARM)University of MilanMilanItaly
  3. 3.Department of Food, Environmental and Nutritional Sciences (DeFENS)University of MilanMilanItaly
  4. 4.Institute of Bio- and Geosciences, IBG-1: Biotechnology, Forschungszentrum Jülich GmbHJülichGermany

Personalised recommendations