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Biocatalytic racemization of sec-alcohols and α-hydroxyketones using lyophilized microbial cells

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Abstract

Biocatalytic racemization of aliphatic and aryl-aliphatic sec-alcohols and α-hydroxyketones (acyloins) was accomplished using whole resting cells of bacteria, fungi, and one yeast. The mild (physiological) reaction conditions ensured the suppression of undesired side reactions, such as elimination or condensation. Cofactor and inhibitor studies suggest that the racemization proceeds through an equilibrium-controlled enzymatic oxidation–reduction sequence via the corresponding ketones or α-diketones, respectively, which were detected in various amounts. Ketone formation could be completely suppressed by exclusion of molecular oxygen.

Biocatalytic racemization whole microbial cells

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Fig. 1
Scheme 1

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Notes

  1. No racemization activity was detected in the following strains: Achromobacter sp. FCC 175, Arthrobacter sp. DSM 7325, Bacillus subtilis 168 DSM 10, Botryosphaeria rhodina DSM 1160, Candida boidinii DSM 70026, Corynespora cassiicola DSM 62475, Cunninghamella blakesleeana DSM 1906, Debaryomyces robertsiae DSM 70870, Fusarium solani FCC 073, Glomerella cingulata DSM 1166, Methylobacterium sp. SM 1793 FCC 031, Mortierella alpina ATCC 8979, Mucor plumbeus CBS 110.16, Mycobacterium gilvum DSM 9487, Mycobacterium paraffinicum NCIMB 10420, Penicillium simplicissimum FCC 072, Pichia angusta DSM 70277, Rhodococcus ruber DSM 44540, R. ruber DSM 44539, R. ruber DSM 43338, Rhodotorula mucilaginosa DSM 70404, Sphingomonas sp. HXN 200 FCC 139, and Yarrowia lipolytica DSM 70651

  2. R. equi IFO 3730 may cause zoonotic infections that affect grazing animals, mainly horses and foals, and is therefore a class II microorganism. Although it is an unlikely cause of infection in humans who are immunocompetent, it may be pathogenic to immunocompromised patients, see: <http://www.nbrc.nite.go.jp/e/index.html>

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Acknowledgments

This study was performed in cooperation between project P18537-B03 of the Austrian Science Fund (FWF) and BASF AG (Ludwigshafen) within the Research Centre Applied Biocatalysis. Financial support by the FWF, the FFG, the City of Graz, and the Province of Styria is gratefully acknowledged. Sonja Heumann and Georg Gübitz from the Graz University of Technology are cordially thanked for their valuable advice in applied microbiology and for the donation of Nocardia G and Nocardia H.

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Authors and Affiliations

  1. Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010, Graz, Austria

    Bettina M. Nestl, Constance V. Voss, Anne Bodlenner, Ursula Ellmer-Schaumberger, Wolfgang Kroutil & Kurt Faber

  2. Research Centre Applied Biochemistry, Petersgasse 14, 8010, Graz, Austria

    Bettina M. Nestl, Anne Bodlenner & Ursula Ellmer-Schaumberger

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  1. Bettina M. Nestl
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  2. Constance V. Voss
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  3. Anne Bodlenner
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  4. Ursula Ellmer-Schaumberger
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  5. Wolfgang Kroutil
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  6. Kurt Faber
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Correspondence to Kurt Faber.

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Nestl, B.M., Voss, C.V., Bodlenner, A. et al. Biocatalytic racemization of sec-alcohols and α-hydroxyketones using lyophilized microbial cells. Appl Microbiol Biotechnol 76, 1001–1008 (2007). https://doi.org/10.1007/s00253-007-1071-0

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  • DOI: https://doi.org/10.1007/s00253-007-1071-0

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