Efficient bioreduction of bicyclo[2.2.2]octane-2,5-dione and bicyclo[2.2.2]oct-7-ene-2,5-dione by genetically engineered Saccharomyces cerevisiae

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Bibtex

@article{72e7b7c7d2e749129c0ad94b50730e19,
title = "Efficient bioreduction of bicyclo[2.2.2]octane-2,5-dione and bicyclo[2.2.2]oct-7-ene-2,5-dione by genetically engineered Saccharomyces cerevisiae",
abstract = "A screening of non-conventional yeast species and several Saccharomyces cerevisiae ( baker's yeast) strains overexpressing known carbonyl reductases revealed the S. cerevisiae reductase encoded by YMR226c as highly efficient for the reduction of the diketones 1 and 2 to their corresponding hydroxyketones 3 - 6 ( Scheme 1) in excellent enantiomeric excesses. Bioreduction of 1 using the genetically engineered yeast TMB4100, overexpressing YMR226c, resulted in > 99{\%} ee for hydroxyketone (+)- 4 and 84 - 98{\%} ee for (-)- 3, depending on the degree of conversion. Baker's yeast reduction of diketone 2 resulted in > 98{\%} ee for the hydroxyketones (+)- 5 and (+)- 6. However, TMB4100 led to significantly higher conversion rates ( over 40 fold faster) and also a minor improvement of the enantiomeric excesses (> 99{\%}).",
author = "Annika Friberg and Ted Johanson and Johan Franzen and Marie-Francoise Gorwa-Grauslund and Torbj{\"o}rn Frejd",
note = "The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240), Applied Microbiology (LTH) (011001021)",
year = "2006",
doi = "10.1039/b603500k",
language = "English",
volume = "4",
pages = "2304--2312",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0539",
publisher = "Royal Society of Chemistry",
number = "11",

}