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

Valerio De Vitis; Benedetta Guidi; Martina Letizia Contente; Tiziana Mariarita Granato; Paola Conti; Francesco Molinari; Elena Crotti; Francesca Mapelli; Sara S. Borin; Daniele Daffonchio; Diego Romano

doi:10.1007/s10126-014-9602-z

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

Valerio De Vitis, Benedetta Guidi, Martina Letizia Contente, Tiziana Mariarita Granato, Paola Conti, Francesco Molinari, Elena Crotti, Francesca Mapelli, Sara S. Borin, Daniele Daffonchio, Diego Romano

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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.

Original language	English (US)
Pages (from-to)	144-152
Number of pages	9
Journal	Marine Biotechnology
Volume	17
Issue number	2
DOIs	https://doi.org/10.1007/s10126-014-9602-z
State	Published - Sep 30 2014

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: F. Mapelli was supported by the Universita 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.

ASJC Scopus subject areas

Aquatic Science
Biotechnology

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1007/s10126-014-9602-z

https://repository.kaust.edu.sa/bitstream/10754/575616/1/10.1007s10126-014-9602-z%20Mar%20Biotechnol.pdf

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De Vitis, V., Guidi, B., Contente, M. L., Granato, T. M., Conti, P., Molinari, F., Crotti, E., Mapelli, F., Borin, S. S., Daffonchio, D., & Romano, D. (2014). Marine Microorganisms as Source of Stereoselective Esterases and Ketoreductases: Kinetic Resolution of a Prostaglandin Intermediate. Marine Biotechnology, 17(2), 144-152. https://doi.org/10.1007/s10126-014-9602-z

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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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AU - Granato, Tiziana Mariarita

AU - Conti, Paola

AU - Molinari, Francesco

AU - Crotti, Elena

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AU - Borin, Sara S.

AU - Daffonchio, Daniele

AU - Romano, Diego

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PY - 2014/9/30

Y1 - 2014/9/30

N2 - 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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Marine Microorganisms as Source of Stereoselective Esterases and Ketoreductases: Kinetic Resolution of a Prostaglandin Intermediate

Abstract

Bibliographical note

ASJC Scopus subject areas

UN SDGs

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