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.

Marine microorganisms as source of stereoselective esterases and ketoreductases : kinetic resolution of a prostaglandin intermediate / V. De Vitis, B. Guidi, M.L. Contente, T. Granato, P. Conti, F. Molinari, E. Crotti, F. Mapelli, S. Borin, D. Daffonchio, D. Romano. - In: MARINE BIOTECHNOLOGY. - ISSN 1436-2228. - 17:2(2015), pp. 144-152. [10.1007/s10126-014-9602-z]

Marine microorganisms as source of stereoselective esterases and ketoreductases : kinetic resolution of a prostaglandin intermediate

V. De Vitis
;
B. Guidi
Secondo
;
M.L. Contente;T. Granato;P. Conti;F. Molinari;E. Crotti;F. Mapelli;S. Borin;D. Daffonchio
Penultimo
;
D. Romano
Ultimo
2015

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.
Biocatalysis; Deep-sea hypersaline anoxic basins (DHABs); Esterase; Ketoreductase; Marine enzymes; Prostaglandin; Stereoselective
Settore CHIM/11 - Chimica e Biotecnologia delle Fermentazioni
Settore CHIM/08 - Chimica Farmaceutica
Settore AGR/16 - Microbiologia Agraria
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/250352
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