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Marine Microorganisms as Source of Stereoselective Esterases and Ketoreductases: Kinetic Resolution of a Prostaglandin Intermediate

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Abstract

A screening among bacterial strains isolated from water-brine interface of the deep hypersaline anoxic basins (DHABs) of the Eastern Mediterranean was carried out for the biocatalytical resolution of racemic propyl ester of anti-2-oxotricyclo[2.2.1.0]heptan-7-carboxylic acid (R,S)-1, a key intermediate for the synthesis of d-cloprostenol. Bacillus horneckiae 15A gave highly stereoselective reduction of (R,S)-1, whereas Halomonas aquamarina 9B enantioselectively hydrolysed (R,S)-1; in both cases, enantiomerically pure unreacted (R)-1 could be easily recovered and purified at molar conversion below 57–58 %, showing the potential of DHAB extremophile microbiome and marine-derived enzymes in stereoselective biocatalysis.

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Acknowledgments

F. Mapelli was supported by the Università degli Studi di Milano, DeFENS, European Social Fund (FSE) and Regione Lombardia (Contract “Dote Ricerca”). This work was supported by the European Community FP7-KBBE.2012.3.2-02 project MACUMBA, grant agreement N. 311975.

Conflict of Interest

The authors declare no conflict of interest.

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Authors and Affiliations

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

    Valerio De Vitis, Benedetta Guidi, Martina Letizia Contente, Tiziana Granato, Francesco Molinari, Elena Crotti, Francesca Mapelli, Sara Borin, Daniele Daffonchio & Diego Romano

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

    Paola Conti

  3. BESE Division, King Abdullah University of Science and Technology, 23955-6900, Thuwal, Kingdom of Saudi Arabia

    Daniele Daffonchio

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  1. Valerio De Vitis
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  2. Benedetta Guidi
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  3. Martina Letizia Contente
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  4. Tiziana Granato
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  5. Paola Conti
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  6. Francesco Molinari
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  7. Elena Crotti
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  8. Francesca Mapelli
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  9. Sara Borin
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  10. Daniele Daffonchio
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  11. Diego Romano
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Correspondence to Diego Romano.

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De Vitis, V., Guidi, B., Contente, M.L. et al. Marine Microorganisms as Source of Stereoselective Esterases and Ketoreductases: Kinetic Resolution of a Prostaglandin Intermediate. Mar Biotechnol 17, 144–152 (2015). https://doi.org/10.1007/s10126-014-9602-z

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  • DOI: https://doi.org/10.1007/s10126-014-9602-z

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