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Enantioselective Baeyer–Villiger Oxidation of Bicyclo[3.2.0]hept-2-en-6-One with Fungi: Optimization of Biotransformation and Use of TiO2 as Support of Cell Growth

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Abstract

Fungi from Amazonian forest soil (Ecuador) and an Italian factory were screened for Baeyer–Villiger (BV) oxidation of bicyclo [3.2.0]hept-2-en-6-one to 2-oxabicyclo[3.3.0]oct-6-en-3-one (Corey’s lactone). Isolates of Fusarium sp. and F. solani produced the (+)-(1R,5S)-lactone while isolates of Aspergillus terricola and A. amazonicus afforded the (−)-(1S,5R)-lactone. Highest conversions (85% yield and 70% enantiomeric excess) were obtained with A. amazonicus grown in presence of 2.7 mM titanium dioxide.

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Authors and Affiliations

  1. Dipartimento di Chimica, Università di Ferrara, Via L. Borsari 46, I-44100 , Ferrara, Italy

    Giancarlo Fantin & Pier Paolo Giovannini

  2. Dipartimento delle Risorse naturali e culturali, Università di Ferrara, C.so Ercole I d’Este 32, I-44100 , Ferrara, Italy

    Alessandra Guerrini, Silvia Maietti, Alessandro Medici & Paola Pedrini

Authors
  1. Giancarlo Fantin
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  2. Pier Paolo Giovannini
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  3. Alessandra Guerrini
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  4. Silvia Maietti
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  5. Alessandro Medici
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  6. Paola Pedrini
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Correspondence to Paola Pedrini.

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Fantin, G., Giovannini, P.P., Guerrini, A. et al. Enantioselective Baeyer–Villiger Oxidation of Bicyclo[3.2.0]hept-2-en-6-One with Fungi: Optimization of Biotransformation and Use of TiO2 as Support of Cell Growth. Biotechnol Lett 28, 805–810 (2006). https://doi.org/10.1007/s10529-006-9000-3

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  • DOI: https://doi.org/10.1007/s10529-006-9000-3

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