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. 2015;65(2):1097-1107.
doi: 10.1007/s13213-014-0955-3. Epub 2014 Aug 22.

Biotransformation of acetophenone and its halogen derivatives by Yarrowia lipolytica strains

Tomasz Janeczko  1 , Wojciech Bąkowski  1 , Ewa Walczak  2 , Małgorzata Robak  3 , Jadwiga Dmochowska-Gładysz  4 , Edyta Kostrzewa-Susłow  1
Affiliations

Biotransformation of acetophenone and its halogen derivatives by Yarrowia lipolytica strains

Tomasz Janeczko et al. Ann Microbiol. 2015.

Abstract

The ability of 16 strains of Yarrowia lipolytica to biotransform acetophenone and its derivatives has been studied. Thirteen of these strains were derived from a wild-type strain Y. lipolytica A-101; six had the invertase gene (SUC2) from Saccharomyces cerevisiae integrated into their genome, as well as the damaged or undamaged gene encoding orotidine-5'-phosphate decarboxylase (URA3), three had integrated the damaged URA3 gene into their genome and three were UV acetate-negative mutants, not able to growth on acetate as the sole carbon source. The other tested strains included two wild strains, A-101 and PMR-1, and an adenine auxotroph ATCC 32-338A. All strains were capable of reducing acetophenone to the R-alcohol in high enantiomeric excess (80-89 %). In all of the cultures tested, reversibility of the reduction was observed, which led to an increase in the enantiomeric excess. nantioselective reduction of the acetophenone halogen derivatives revealed that the nature and location of the halogen atom had a significant influence on the enantioselectivity of the reduction. In the culture of ATCC 32-338A, after a 3-day biotransformation of 2,4'-dibromoacetophenone the enantiopure R-alcohol was obtained at a rate of 100 % of substrate conversion. In conclusion, using these invertase-containing strains or uracyl auxotrophs provided no additional benefit in terms of biotransformation capacity over the parental strain.

Keywords: Enantiospecific reduction; Halogen derivatives of acetophenone; SUC2; URA3; Yarrowia lipolytica.

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Figures

Fig. 1
Fig. 1
Reduction of acetophenone (1) to (R)-1-phenylethan-1-ol [(R)-2] and to (S)-1-phenylethan-1-ol [(S)-2)] by Yarrowia lipolytica strains
Fig. 2
Fig. 2
Time-course of biotransformation of acetophenone (1) by Y. lipolytica B55-3 (a) and Y. lipolytica ATCC 32-338A (b)
Fig. 3
Fig. 3
Time-course of biotransformation of 1-phenylethan-1-ol (2) by Y. lipolytica B9-2
Fig. 4
Fig. 4
Halogen derivatives of acetophenone (1): 2,4′-dichloroacetophenone (3), 2,2′,4′-trichloroacetophenone (4), 2-chloro-4′-fluoroacetophenone (5), 2-bromo-4′-chloroacetophenone (6) and 2,4′-dibromoacetophenone (7). (2), (8–12) Racemic alcohols
Fig. 5
Fig. 5
Time-course of biotransformation of 2-bromo-4′-chloroacetophenone (6) by Y. lipolytica A-101
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