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

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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.).

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References

  1. Nakamura K, Matsuda T (2006) Curr Org Chem 10:1217–1246

    Article  CAS  Google Scholar 

  2. Hoyos P, Sinisterra JV, Molinari F, Alcantara AR, Dominguez de Maria P (2010) Acc Chem Res 43:288–299

    Article  CAS  Google Scholar 

  3. Sehl T, Hailes HC, Ward JM, Menyes U, Pohl M, Rother D (2014) Green Chem 16:3341–3348

    Article  CAS  Google Scholar 

  4. Chen Y, Chen C, Wu X (2012) Chem Soc Rev 41:1742–1753

    Article  CAS  Google Scholar 

  5. Kalaitzakis D, Rozzell JD, Smonou I, Kambourakis S (2006) Adv Synth Catal 348:1958–1969

    Article  CAS  Google Scholar 

  6. Kalaitzakis D, Smonou I (2010) J Org Chem 75:8658–8661

    Article  CAS  Google Scholar 

  7. Bataille CJR, Donohoe TJ (2011) Chem Soc Rev 40:114–128

    Article  CAS  Google Scholar 

  8. Nguyen TN, Chen PA, Setthakarn K, May JA (2018) Molecules 23:2317

    Article  Google Scholar 

  9. Paterson I, Chen DYK, Acena JL, Franklin AS (2000) Org Lett 2:1513–1516

    Article  CAS  Google Scholar 

  10. Mukai K, Urabe D, Kasura S, Aoki N, Inoue MA (2013) Angew Chem Int Ed 52:5300–5304

    Article  CAS  Google Scholar 

  11. Urabe D, Nakagawa Y, Mukai K, Fukushima K, Aoki N, Itoh H, Nagatomo M, Inoue M (2018) J Org Chem 83:13888–13910

    Article  CAS  Google Scholar 

  12. Haberland J, Kriegesmann A, Wolfram E, Hummel W, Liese A (2002) Appl Microbiol Biotechnol 58:595–599

    Article  CAS  Google Scholar 

  13. Grau BT, Devine PN, Di Michele LN, Kosjek B (2007) Org Lett 9:4951–4954

    Article  CAS  Google Scholar 

  14. Lüdeke S, Richter M, Müller M (2009) Adv Synth Catal 351:253–259

    Article  Google Scholar 

  15. Kurina-Sanz M, Bisogno FR, Lavandera I, Orden AA, Gotor V (2009) Adv Synth Catal 351:1842–1848

    Article  CAS  Google Scholar 

  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 353:2359–2362

    Article  CAS  Google Scholar 

  17. Mourelle-Insua A, de Gonzalo G, Lavandera I, Gotor-Fernández V (2018) Catalysts 8:150

    Article  Google Scholar 

  18. Brooks W, Mazdiyasni M, Grothaus PG (1987) J Org Chem 52:3223–3232

    Article  CAS  Google Scholar 

  19. Watanabe W, Iwamoto M, Nakada M (2005) J Org Chem 70:4652–4658

    Article  CAS  Google Scholar 

  20. Kosmol H, Kieslich K, Vossing R, Koch HJ, Petzoldt K, Gibian H (1967) Justus Liebigs Ann Chem 701:199–205

    Article  Google Scholar 

  21. Contente ML, Molinari F, Serra I, Pinto A, Romano D (2016) Eur J Org Chem 2016:1260–1263

    Article  CAS  Google Scholar 

  22. Contente ML, Serra I, Brambilla M, Eberini I, Gianazza E, De Vitis V, Molinari F, Zambelli P, Romano D (2016) Appl Microbiol Biotechnol 100:193–201

    Article  CAS  Google Scholar 

  23. Contente ML, Serra I, Molinari F, Gandolfi R, Pinto A, Romano D (2016) Tetrahedron 72:3974–3979

    Article  CAS  Google Scholar 

  24. Contente ML, Molinari F, Zambelli P, De Vitis V, Gandolfi R, Pinto A, Romano D (2014) Tetrahedron Lett 55:7051–7053

    Article  CAS  Google Scholar 

  25. Contente ML, Zambelli P, Galafassi S, Tamborini L, Pinto A, Conti P, Molinari F, Romano D (2015) J Mol Catal B 114:7–12

    Article  CAS  Google Scholar 

  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 14:3404–3408

    Article  CAS  Google Scholar 

  27. Dall’Oglio F, Contente ML, Conti P, Molinari F, Monfredi D, Pinto A, Romano D, Ubiali D, Tamborini L (2017) Catal Commun 93:29–32

    Article  Google Scholar 

  28. Manna MS, Mukherjee S (2014) Chem Sci 5:1627–1633

    Article  CAS  Google Scholar 

  29. Byrne SJ, Fletcher AJ, Hebeisen P, Willis MC (2010) Org Biomol Chem 8:758–760

    Article  CAS  Google Scholar 

  30. Oeggl R, Neumann T, Gätgens J, Romano D, Noack S, Rother D (2018) Front Bioeng Biotechnol 6:196

    Article  Google Scholar 

  31. Yeung YY, Chein RJ, Corey EJ (2007) J Am Chem Soc 129:10346–10347

    Article  CAS  Google Scholar 

  32. Kolakowski RV, Manpadi M, Zhang Y, Emge TJ, Williams LJ (2009) J Am Chem Soc 131:12910–12911

    Article  CAS  Google Scholar 

  33. Salter GJ, Kell DB (1995) Crit Rev Biotechnol 15:139–177

    Article  CAS  Google Scholar 

Download references

Acknowledgements

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

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Author notes

  1. Martina Letizia Contente and Federica Dall’Oglio have contributed equally to this work.

Authors and Affiliations

  1. School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK

    Martina Letizia Contente

  2. Department of Pharmaceutical Sciences (DISFARM), University of Milan, via Mangiagalli 25, 20133, Milan, Italy

    Federica Dall’Oglio, Francesca Annunziata & Lucia Tamborini

  3. Department of Food, Environmental and Nutritional Sciences (DeFENS), University of Milan, via Mangiagalli 25, 20133, Milan, Italy

    Martina Letizia Contente, Francesco Molinari, Marco Rabuffetti, Diego Romano & Andrea Pinto

  4. Institute of Bio- and Geosciences, IBG-1: Biotechnology, Forschungszentrum Jülich GmbH, 52425, Jülich, Germany

    Dörte Rother

Authors
  1. Martina Letizia Contente
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  2. Federica Dall’Oglio
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  3. Francesca Annunziata
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  9. Andrea Pinto
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Correspondence to Andrea Pinto.

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Contente, M.L., Dall’Oglio, F., Annunziata, F. et al. Stereoselective Reduction of Prochiral Cyclic 1,3-Diketones Using Different Biocatalysts. Catal Lett 150, 1176–1185 (2020). https://doi.org/10.1007/s10562-019-03015-y

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  • DOI: https://doi.org/10.1007/s10562-019-03015-y

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