Strain engineering for stereoselective bioreduction of dicarbonyl compounds by yeast reductases

Johanson, Ted; Katz, Michael J.; Gorwa-Grauslund, Marie-Françoise

doi:10.1016/j.femsyr.2004.12.006

Cited by 45 publications

(25 citation statements)

References 83 publications

(150 reference statements)

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“…A number of microbiological syntheses have been developed to produce chiral compounds (Goldberg et al 2007; Johanson et al 2005). One of these is (R)-3-hydroxybutyric acid [(R)-3-HB], which is the monomer of the polymer polyhydroxybutyrate (PHB).…”

Section: Introductionmentioning

confidence: 99%

Production of (R)-3-hydroxybutyric acid by Arxula adeninivorans

Biernacki

Riechen²,

Hähnel

et al. 2017

AMB Expr

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(R)-3-hydroxybutyric acid can be used in industrial and health applications. The synthesis pathway comprises two enzymes, β-ketothiolase and acetoacetyl-CoA reductase which convert cytoplasmic acetyl-CoA to (R)-3-hydroxybutyric acid [(R)-3-HB] which is released into the culture medium. In the present study we used the non-conventional yeast, Arxula adeninivorans, for the synthesis enantiopure (R)-3-HB. To establish optimal production, we investigated three different endogenous yeast thiolases (Akat1p, Akat2p, Akat4p) and three bacterial thiolases (atoBp, thlp, phaAp) in combination with an enantiospecific reductase (phaBp) from Cupriavidus necator H16 and endogenous yeast reductases (Atpk2p, Afox2p). We found that Arxula is able to release (R)-3-HB used an existing secretion system negating the need to engineer membrane transport. Overexpression of thl and phaB genes in organisms cultured in a shaking flask resulted in 4.84 g L−1 (R)-3-HB, at a rate of 0.023 g L−1 h−1 over 214 h. Fed-batch culturing with glucose as a carbon source did not improve the yield, but a similar level was reached with a shorter incubation period [3.78 g L−1 of (R)-3-HB at 89 h] and the rate of production was doubled to 0.043 g L−1 h−1 which is higher than any levels in yeast reported to date. The secreted (R)-3-HB was 99.9% pure. This is the first evidence of enantiopure (R)-3-HB synthesis using yeast as a production host and glucose as a carbon source.

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Section: Introductionmentioning

confidence: 99%

Production of (R)-3-hydroxybutyric acid by Arxula adeninivorans

Biernacki

Riechen²,

Hähnel

et al. 2017

AMB Expr

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“…Among these methods, whole cell catalyzed bioreduction with yeast is the most appealing means due to its cost eVectiveness [10].…”

Section: Introductionmentioning

confidence: 99%

Effects of industrial storage on the bioreduction capacity of brewer’s yeast

Yu¹,

Hou²,

Gong³

et al. 2008

J Ind Microbiol Biotechnol

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The effects of industrial storage on the changes of the cell viability and the activities of intracellular alcohol dehydrogenase (ADH) and glucose-6-phosphate dehydrogenase (G6PDH) in brewer's yeast, and the corresponding capacity for the bioconversion of ethyl-3-oxobutanoate (EOB) to ethyl (S)-3-hydroxybutanoate ((S)-EHB), were investigated. The viability of fresh brewer's yeast cells stored in industrial circulating cooling water at 1-2 degrees C showed 4 and 15% drop after the storage of 7 and 15 days, respectively, after which cells died rapidly. The pretreatment of the stored brewer's yeast cells by washing and screening significantly enhanced cell viability during industrial storage. The intracellular levels of ADH and G6PDH after permeabilization of these stored cells with cetyltrimetylammonium bromide (CTAB) were much higher, which showed only slight decrease within 2 weeks during the industrial storage. When the stored cells after the permeabilization treatment was used as the biocatalyst at 90-120 g/L, EOB was converted almost completely into enantiopure (S)-EHB with an enantiomeric excess (ee) more than 99% and a yield of over 96%, by fed-batch bioconversion of 560 mM EOB within 6 h.

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“…In turn, ethanol proved to be an interesting alternative to glucose as co-substrate to regenerate cofactors. However, it is toxic to the cells at higher concentration [22]. …”

Section: Resultsmentioning

confidence: 99%

Biotransformation of α-Acetylbutyrolactone in Rhodotorula Strains

Mączka

Wińska

Grabarczyk

et al. 2018

IJMS

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Due to its structural similarity, the α’-1′-hydroxyethyl-γ-butyrolactone obtained by reduction of (±)-α-acetyl-γ-butyrolactone may have a similar function in the body to γ-butyrolactone (GBL). In the work presented, biotransformation of α-acetyl-γ-butyrolactone by three Rhodotorula strains was performed obtaining enantiomerically enriched alcohol. The process was carried out in growing and resting cultures. We studied how both media composition and organic solvent volume affected stereoselectivity and effectiveness of biotransformation. After 2 h, the enantiomerically pure (3R, 1′S)-α’-1′-hydroxyethyl-γ-butyrolactone was obtained using the R. marina AM77 strain in YPG (Yeast extract-Peptone-Glucose) medium enriched with 5% glycerol. To our best knowledge there is no previous information in the literature about the (±)-α-acetyl-γ-butyrolactone biotransformation performed in medium with addition of organic and deep eutectic solvents.

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Strain engineering for stereoselective bioreduction of dicarbonyl compounds by yeast reductases

Cited by 45 publications

References 83 publications

Production of (R)-3-hydroxybutyric acid by Arxula adeninivorans

Production of (R)-3-hydroxybutyric acid by Arxula adeninivorans

Effects of industrial storage on the bioreduction capacity of brewer’s yeast

Biotransformation of α-Acetylbutyrolactone in Rhodotorula Strains

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