Highly Regio- and Enantioselective Reduction of 1-Chloro-2,4-alkanediones Using Baker's Yeast: Effects of Organic Solvents as Additives

Cui, Jing; Teraoka, R.; Ema, Tadashi; Sakai, Takashi; Utaka, Masanori

doi:10.1016/s0040-4039(97)00524-8

Cited by 20 publications

(8 citation statements)

References 7 publications

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“…Combining overexpression and knockout strategies would significantly enhance the levels of stereoselectivity of the baker's yeast93. Alternatively, the enantioselectivity of the reduction process can also be controlled using thermal pretreated baker's yeast, which has been successfully carried out in the reduction of 3‐oxoalkanoates62, 117, α‐diketones70, 77 and 2,4‐alkanediones25. Addition of poisoning agents that inhibit undesirable enzymatic activities, the use of a two‐phase system, substrate modifications and a change of energy source (carbon or growing conditions) have been shown to provide equal usefulness90, 93.…”

Section: Challenges and Opportunitiesmentioning

confidence: 99%

Saccharomyces cerevisiae: a potential stereospecific reduction tool for biotransformation of mono‐ and sesquiterpenoids

Khor

Uzir

2010

Yeast

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Terpenes and terpenoids are among the key impact substances in the food and fragrance industries. Equipped with pharmacological properties and applications as ideal precursors for the biotechnological production of natural aroma chemicals, interests in these compounds have been escalating. Hence, the syntheses of new derivatives that can show improved properties are often called for. Stereoselective biotransformation offers several benefits to increase the rate of production, in terms of both the percentage yield and its enantiomeric excesses. Baker's yeast (Saccharomyces cerevisiae) is broadly used as a whole cell stereospecific reduction biocatalyst, due to its capability in reducing carbonyls and carbon-carbon double bonds, which also extends its functionality as a versatile biocatalyst in terpenoid biotransformation. This review provides some insights on the development and prospects in the reductive biotransformation of monoterpenoids and sesquiterpenoids using S. cerevisiae, with an overview of strategies to overcome the common challenges in large-scale implementation.

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Section: Challenges and Opportunitiesmentioning

confidence: 99%

Saccharomyces cerevisiae: a potential stereospecific reduction tool for biotransformation of mono‐ and sesquiterpenoids

Khor

Uzir

2010

Yeast

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“…332 Many functional groups are compatible with asymmetric ketone reduction, including nitriles, 333 carboxylic acids, 334 sulfones 335,336 and halides. 336,337 In some cases reduction may be carried out together with ester hydrolysis, thus combining two useful processes into one step. 338 The reduction of ketone 51 containing an adjacent oxime ether, gives the corresponding alcohol 52 in 97% ee when Bakers' yeast was used.…”

Section: Reductions and Oxidationsmentioning

confidence: 99%

Asymmetric catalysts

Wills¹,

Tye²

1999

J. Chem. Soc., Perkin Trans. 1

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“…This regiospecificity is impressive when it is compared, for example, to the result that the reduction of 7 with NaBH 4 in water showed little regioselectivity even at 0 °C. Furthermore, the regioselectivity of the reductase was changed when 1-substituted-2,4-pentanediones 5 and 6 were used (Table ), indicating that in this case the chemical reactivity of the functional groups dominates over the steric effect …”

Section: Discussionmentioning

confidence: 66%

“…A large amount (51%) of furanone 15 was obtained. i The values reported in ref (with dry BY) are 53 (29, S ). j The values reported in ref (with dry BY) are 42 (82).…”

Section: Resultsmentioning

confidence: 99%

Highly Enantioselective Reduction of Carbonyl Compounds Using a Reductase Purified from Bakers' Yeast

et al. 1998

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An NADPH-dependent reductase that shows reducing activity for 1-chloro-2-hexanone has been purified from bakers' yeast. SDS−PAGE and gel filtration suggested that the purified reductase is a monomeric enzyme with a molecular weight of ca. 37 kDa. Asymmetric reduction of several carbonyl compounds using the purified reductase has been carried out. 1-Chloro-2-hexanone, 1-acetoxy-2-heptanone, methyl acetoacetate, ethyl pyruvate, 1-chloro-2,4-pentanedione, and 2,4-hexanedione were reduced to the corresponding alcohols with high enantiomeric purities (>98% ee). The reductase showed high specificity constants (k cat/K m = 103−105 s-1 M-1) and relatively low Michaelis constants (K m = 10-4−10-3 M) for all the substrates examined.

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Highly Regio- and Enantioselective Reduction of 1-Chloro-2,4-alkanediones Using Baker's Yeast: Effects of Organic Solvents as Additives

Cited by 20 publications

References 7 publications

Saccharomyces cerevisiae: a potential stereospecific reduction tool for biotransformation of mono‐ and sesquiterpenoids

Saccharomyces cerevisiae: a potential stereospecific reduction tool for biotransformation of mono‐ and sesquiterpenoids

Asymmetric catalysts

Highly Enantioselective Reduction of Carbonyl Compounds Using a Reductase Purified from Bakers' Yeast

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