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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. 1.

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

  2. 2.

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

  3. 3.

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

  4. 4.

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

  5. 5.

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

  6. 6.

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

  7. 7.

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

  8. 8.

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

  9. 9.

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

  10. 10.

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

  11. 11.

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

  12. 12.

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

  13. 13.

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

  14. 14.

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

  15. 15.

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

  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 353:2359–2362

  17. 17.

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

  18. 18.

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

  19. 19.

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

  20. 20.

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

  21. 21.

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

  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 100:193–201

  23. 23.

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

  24. 24.

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

  25. 25.

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

  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 14:3404–3408

  27. 27.

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

  28. 28.

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

  29. 29.

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

  30. 30.

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

  31. 31.

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

  32. 32.

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

  33. 33.

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

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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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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 (2019). https://doi.org/10.1007/s10562-019-03015-y

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Keywords

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