Reductions of 3-oxo Esters by Baker's Yeast: Current Status

The objective of the current review is to present a mechanism and process engineering approach of stereospecific reductions of 3-oxo esters by baker's yeast. The stereospecific outcome of a reduction by baker's yeast depends on the kind of 3-oxo ester reductases involved and their specific activity. Various competing 3-oxo ester reductases are present in a yeast cell. An important aspect for efficient biotransformations with whole cells is the regeneration of NADH and NADPH cofactors. Use of different electron donors leads to the involvement of different metabolic routes influencing the reduction process. Optimization of the process conditions such as aeration, immobilization of cells, use of additives, or use of two phases, will enhance re-use of baker's yeast, yield, stereospecific outcome and scale up. Since the genome of baker's yeast is known, genetic engineering will soon increase the possibilities of stereoselective reductions.

[1]  S. Oliver,et al.  Erratum: Overview of the yeast genome , 1997, Nature.

[2]  M. Zmijewski,et al.  Large-scale stereoselective enzymatic ketone reduction with in situ product removal via polymeric adsorbent resins , 1997 .

[3]  N. Meinander,et al.  Influence of cosubstrate concentration on xylose conversion by recombinant, XYL1-expressing Saccharomyces cerevisiae: a comparison of different sugars and ethanol as cosubstrates , 1997, Applied and environmental microbiology.

[4]  T. Ema,et al.  Highly Regio- and Enantioselective Reduction of 1-Chloro-2,4-alkanediones Using Baker's Yeast: Effects of Organic Solvents as Additives , 1997 .

[5]  A. Smallridge,et al.  The stereoselective preparation of β-hydroxy esters using a yeast reduction in an organic solvent , 1997 .

[6]  J. Pronk,et al.  Pyruvate Metabolism in Saccharomyces cerevisiae , 1996, Yeast.

[7]  R. Lanciotti,et al.  Effect of high hydrostatic pressure and high pressure homogenization on the enantioselectivity of microbial reductions , 1996 .

[8]  N. Nakajima,et al.  Protein sequences of two keto ester reductases: possible identity as hypothetical proteins. , 1996, Bioscience, biotechnology, and biochemistry.

[9]  J. Krisch,et al.  Continuous production of ethanol using yeast cells immobilized in preformed cellulose beads , 1996, Applied Microbiology and Biotechnology.

[10]  D. Toke,et al.  Isolation and Characterization of a Gene Affecting Fatty Acid Elongation in Saccharomyces cerevisiae* , 1996, The Journal of Biological Chemistry.

[11]  S. W. Kim,et al.  Development of new alginate fiber for the immobilization of yeast , 1996 .

[12]  R. Matsuno,et al.  Large-scale production of chiral alcohols with bakers' yeast , 1996 .

[13]  R. D. S. Pereira.  Baker's yeast. Some biochemical aspects and their influence in biotransformations. , 1995, Applied biochemistry and biotechnology.

[14]  O. Ward,et al.  Reductive biotransformations of 2-substituted-3-carbonyl butanoate by resting cells and an enzymatic system of Geotrichum sp. , 1995 .

[15]  B. Prior,et al.  Purification and partial characterization of an aldo-keto reductase from Saccharomyces cerevisiae , 1995, Applied and environmental microbiology.

[16]  R. Matsuno,et al.  Relationship between ethanol consumption rate and prochiral ketone reduction rate in bakers' yeast , 1995 .

[17]  R. Holt,et al.  Yeast Catalysed Reduction of β-Keto Esters (2): Optimisation of the Stereospecific Reduction by Zygosaccharomyces Rouxii , 1995 .

[18]  J. Murrell,et al.  Yeast Catalysed Reduction of β-Keto Esters (1): Factors Affecting Whole-Cell Catalytic Activity and Stereoselectivity , 1995 .

[19]  Kaoru Nakamura,et al.  Purification and Characterization of α-Keto Ester Reductases from Bakers’ Yeast , 1994 .

[20]  K. Ishihara,et al.  Asymmetric Reduction of 1-Acetoxy-2-alkanones with Bakers' Yeast: Purification and Characterization of .ALPHA.-Acetoxy Ketone Reductase. , 1994 .

[21]  N. Nakajima,et al.  Differences in protein structure and similarities in catalytic function of two L-stereoselective carbonyl reductases from bakers' yeast. , 1994, Bioscience, biotechnology, and biochemistry.

[22]  H. Ohta,et al.  Biochemical Reduction of 3-Oxoalkanoic Esters by a Bottom-fermentation Yeast, Saccharomyces cerevisiae IFO 0565 , 1994 .

[23]  A. Smallridge,et al.  The Use of Organic Solvent Systems in the Yeast Mediated Reduction of Ethyl Acetoacetate , 1994 .

[24]  Kaoru Nakamura,et al.  Stereochemical Control in Microbial Reduction. XXIII. Thermal Treatment of Bakers’ Yeast for Controlling the Stereoselectivity of Reductions , 1994 .

[25]  S. Kondo,et al.  Effect of cyclodextrin on improvement of enantioselectivity in the reduction of ketopantolactone with baker's yeast. , 1994, Bioorganic & medicinal chemistry.

[26]  T. D'amore,et al.  Physiological effects of yeast cell immobilization Applications for brewing , 1994 .

[27]  H. V. van Vuuren,et al.  Molecular analysis of the malic enzyme gene (mae2) of Schizosaccharomyces pombe , 1994, Yeast.

[28]  S. Servi,et al.  Old and New Synthetic Capacities of Baker's Yeast , 1994 .

[29]  R. Matsuno,et al.  NAD(P)H Regeneration Using Ethanol as an Energy Source in Baker's Yeast-Mediated Bioreduction , 1994 .

[30]  Kaoru Nakamura,et al.  Stereochemical Control in Microbial Reduction. XXI. Effect of Organic Solvents on Reduction of α-Keto Esters Mediated by Bakers’ Yeast , 1993 .

[31]  C. Sih,et al.  Stereochemical control of yeast reductions. 6. Diastereoselectivity of 2-alkyl-3-oxobutanoate oxido-reductases. , 1993 .

[32]  Yuji Tanaka,et al.  Allyl bromide, a powerful inhibitor against R-enzyme activities in Bakers' yeast reduction of ethyl 3-oxoalkanoates , 1993 .

[33]  R. Matsuno,et al.  Large-scale preparation of (S)-ethyl 3-hydroxybutanoate with a high enantiomeric excess through baker's yeast-mediated bioreduction , 1993 .

[34]  R. V. Prasad,et al.  A strategy for increasing an in vivo flux by genetic manipulations. The tryptophan system of yeast. , 1992, The Biochemical journal.

[35]  C. Verduyn,et al.  Energetic aspects of metabolic fluxes in yeasts , 1992 .

[36]  Ramesh N. Patel,et al.  Stereoselective reduction of β-keto esters by Geotrichum candidum , 1992 .

[37]  B. Griffin.  Functional and structural relationships among aldose reductase, L-hexonate dehydrogenase (aldehyde reductase), and recently identified homologous proteins. , 1992, Enzyme and microbial technology.

[38]  E. Santaniello,et al.  The Biocatalytic Approach to the Preparation of Enantiomerically Pure Chiral Building Blocks , 1992 .

[39]  H. Yamada,et al.  Enzymes Involved in the NADPH Regeneration System Coupled with Asymmetric Reduction of Carbonyl Compounds in Microorganisms. , 1992, Bioscience, biotechnology, and biochemistry.

[40]  Kurt Faber,et al.  Biotransformations in Organic Chemistry , 1992 .

[41]  Yasushi Kawai,et al.  Stereochemical Control of Microbial Reduction. Part 17. A Method for Controlling the Enantioselectivity of Reductions with Bakers′ Yeast. , 1991 .

[42]  O. Ward,et al.  Studies of the reductive biotransformation of selected carbonyl compounds by whole cells and extracts of baker's yeast, Saccharomyces carevisiae , 1991, Biotechnology and bioengineering.

[43]  Kazutoshi Ushio,et al.  Selective inhibition of R-enzymes by simple organic acids in yeast-catalysed reduction of ethyl 3-oxobutanoate , 1991 .

[44]  Yasushi Kawai,et al.  Stereochemical control of microbial reduction. 17. A method for controlling the enantioselectivity of reductions with bakers' yeast , 1991 .

[45]  J. Bailey,et al.  Toward a science of metabolic engineering , 1991, Science.

[46]  G. Stephanopoulos,et al.  Network rigidity and metabolic engineering in metabolite overproduction , 1991, Science.

[47]  Kaoru Nakamura,et al.  Stereochemical control in microbial reduction. 19. Effect of heat-treatment on the diastereoselectivity in the reduction with baker's yeast , 1991 .

[48]  Kaoru Nakamura,et al.  Stereochemical Control in Microbial Reduction. 18. Mechanism of Stereochemical Control in the Diastereoselective Reduction with Baker’s Yeast , 1991 .

[49]  R. Matsuno,et al.  Bioreduction of Ketones Mediated by Baker’s Yeast with Acetate as Ultimate Reducing Agent , 1991 .

[50]  Y. Naoshima,et al.  Asymmetric bioreduction of keto esters by immobilized baker's yeast entrapped in calcium alginate beads in both water and organic/water solvent systems , 1991, World journal of microbiology & biotechnology.

[51]  R. Haselbeck,et al.  Isolation, nucleotide sequence, and disruption of the Saccharomyces cerevisiae gene encoding mitochondrial NADP(H)-specific isocitrate dehydrogenase. , 1991, The Journal of biological chemistry.

[52]  R. Csuk,et al.  Baker's yeast mediated transformations in organic chemistry , 1991 .

[53]  R. Matsuno,et al.  Baker's yeast mediated bioreduction: Practical procedure using EtOH as energy source , 1991 .

[54]  Kaoru Nakamura,et al.  Asymmetric Reduction of Ketones with Microbes , 1990 .

[55]  O. Ward,et al.  Reductive biotransformations of organic compounds by cells or enzymes of yeast. , 1990, Enzyme and microbial technology.

[56]  T. Gianferrara,et al.  Chemometric optimization of an asymmetric reduction catalyzed by baker's yeast , 1990, Biotechnology and bioengineering.

[57]  R. Tressl,et al.  Purification and properties of two oxidoreductases catalyzing the enantioselective reduction of diacetyl and other diketones from baker's yeast. , 1990, European journal of biochemistry.

[58]  Nigel S. Scrutton,et al.  Redesign of the coenzyme specificity of a dehydrogenase by protein engineering , 1990, Nature.

[59]  S. Servi.  Baker's Yeast as a Reagent in Organic Synthesis , 1990 .

[60]  D. Papahatjis,et al.  Enhanced optical purity of 3-hydroxyesters obtained by baker's yeast reduction of 3-ketoesters , 1990 .

[61]  Kaoru Nakamura,et al.  A novel method to synthesize (L)-β-hydroxyl esters by the reduction with bakers' yeast , 1990 .

[62]  H. Lommi,et al.  Immobilized yeast reactor speeds beer production , 1990 .

[63]  T. Sato,et al.  Stereocontrol in Bakers' Yeast Reduction Leading to Natural Product Synthesis , 1990 .

[64]  Kaoru Nakamura,et al.  Stereochemical Control in Microbial Reduction. Part 10. Asymmetric Reduction of Alkyl 3-Methyl-2-Oxobutanoate with Immobilized Bakers' Yeast in Hexane , 1990 .

[65]  A. Fiechter,et al.  Process for the Stereoselective Biotransformation of Acetoacetic Acid Esters Using Yeasts , 1990 .

[66]  G. Skjåk-Bræk,et al.  Alginate as immobilization matrix for cells. , 1990, Trends in biotechnology.

[67]  Kaoru Nakamura,et al.  Asymmetric Reduction of Ketones with Microbes (Commemoration Issue Dedicated to Professor Shinzaburo OKA On the Occasion of His Retirement) , 1989 .

[68]  K. Mori.  Synthesis of optically active pheromones , 1989 .

[69]  R. Matsuno,et al.  Baker’s Yeast Mediated Bioreduction. A New Procedure Using Ethanol as an Energy Source , 1989 .

[70]  Kaoru Nakamura,et al.  Stereochemical Control in Microbial Reduction. 8. Stereochemical Control in Microbial Reduction of β-Keto Esters , 1989 .

[71]  H. Yamada,et al.  Ketopantoyl lactone reductase is a conjugated polyketone reductase. , 1989, FEMS microbiology letters.

[72]  Y. Akakabe,et al.  Biotransformation of Acetoacetic Esters with Immobilized Cells of Nicotiana tabacum , 1989 .

[73]  Kaoru Nakamura,et al.  A new method for stereochemical control of microbial reduction. Reduction of β-keto esters with bakers' yeast immobilized by magnesium alginate , 1989 .

[74]  Kaoru Nakamura,et al.  Stereochemical control on yeast reduction of .alpha.-keto esters. Reduction by immobilized bakers' yeast in hexane , 1988 .

[75]  K. Engel,et al.  Purification and characterization of two oxidoreductases involved in the enantioselective reduction of 3-oxo, 4-oxo and 5-oxo esters in baker's yeast. , 1988, European journal of biochemistry.

[76]  N. Oguni,et al.  Complete stereoselective synthesis of chiral intermediates for thienamycin and related antibiotics , 1988 .

[77]  M. Christen,et al.  Biotransformation in organic synthesis: applications of yeast reduction in the synthesis of 3,5-dihydroxy esters of high optical purity , 1988 .

[78]  Kaoru Nakamura,et al.  Effect of allyl alcohol on reduction of β-keto esters by bakers' yeast , 1987 .

[79]  J. M. Salmon.  Determination of malic enzyme activity on permeabilized cells of Saccharomyces cerevisiae using a dissolved CO2 probe , 1987 .

[80]  E. Santaniello,et al.  Studies on the stereochemical control of fermenting baker's yeast mediated reductions: some 3- and 4-oxo esters , 1987 .

[81]  C. Sih,et al.  A Model For Predicting Diastereoselectivity In Yeast Reductions , 1987 .

[82]  S. Vries,et al.  The mitochondrial respiratory chain of yeast. Structure and biosynthesis and the role in cellular metabolism. , 1987, Biochimica et biophysica acta.

[83]  D. Seebach,et al.  Stereoselectivity of Yeast Reductions. An Improved Procedure for the Preparation of Ethyl(S)-3-hydroxybutanoate and (S)-2-Hydroxymethylbutanoate. , 1986 .

[84]  Douglas B. Kell,et al.  Metabolic control theory: its role in microbiology and biotechnology , 1986 .

[85]  P. M. Bruinenberg,et al.  A comparative radiorespirometric study of glucose metabolism in yeasts , 1986, Yeast.

[86]  Johannes P. van Dijken,et al.  Redox balances in the metabolism of sugars by yeasts (NAD(H); NADP(H); glucose metabolism; xylose fermentation; ethanol; Crabtree effect; Custers effect) , 1986 .

[87]  P. Seneci,et al.  Further information on the steric course of the baker's yeast reduction of 4-substituted-3-oxobutanoates , 1986 .

[88]  Kaoru Nakamura,et al.  Stereochemical control in microbial reduction 4. Effect of cultivation conditions on the reduction of β-keto esters by methylotrophic yeasts. , 1986 .

[89]  K. Horikoshi,et al.  Purification and Properties of an Asymmetric Reduction Enzyme of 2-Methyl-3-oxobutyrate in Baker's Yeast , 1985 .

[90]  Kunihiko Watanabe,et al.  Metabolism of 2‐oxoaldehyde in yeasts , 1985 .

[91]  C. Sih,et al.  Stereochemical control of yeast reductions. 5. Characterization of the oxidoreductases involved in the reduction of .beta.-keto esters , 1985 .

[92]  Kaoru Nakamura,et al.  Stereochemical control of microbial reduction. 2. Reduction of β-keto esters by immobilized bakers' yeast , 1985 .

[93]  C. Sih,et al.  Enantioselective Reductions of β‐keto‐Esters by Bakers' Yeast , 1984 .

[94]  C. Sih,et al.  Microbial Asymmetric Catalysis—Enantioselective Reduction of Ketones [New Synthetic Methods (45)] , 1984 .

[95]  C. Sih,et al.  Stereochemical control of yeast reductions. 2. Quantitative treatment of the kinetics of competing enzyme systems for a single substrate , 1984 .

[96]  D. Seebach,et al.  Preparative Microbial Reduction of β‐Oxoesters with Thermoanaerobium brockii , 1984 .

[97]  Kaoru Nakamura,et al.  Stereochemical control in yeast reduction. , 1984 .

[98]  R A Cooper,et al.  Metabolism of methylglyoxal in microorganisms. , 1984, Annual review of microbiology.

[99]  C. Sih,et al.  Stereochemical control of yeast reductions. 1. Asymmetric synthesis of L-carnitine , 1983 .

[100]  J. A. Roels,et al.  Energetics and Kinetics in Biotechnology , 1983 .

[101]  P. M. Bruinenberg,et al.  A Theoretical Analysis of NADPH Production and Consumption in Yeasts , 1983 .

[102]  P. M. Bruinenberg,et al.  An enzymic analysis of NADPH production and consumption in Candida utilis. , 1983, Journal of general microbiology.

[103]  B. Wipf,et al.  Production of (+)‐(S)‐Ethyl 3‐Hydroxybutyrate and (‐)‐(R)‐Ethyl 3‐Hydroxybutyrate by Microbial Reduction of Ethyl Acetoacetate , 1983 .

[104]  K. Mori.  A simple synthesis of (S)-(+)-sulcatol, the pheromone of gnathotrichus retusus, employing baker's yeast for asymmetric reduction , 1981 .

[105]  O. Käppeli,et al.  Regulation of glucose metabolism in growing yeast cells. , 1981, Advances in microbial physiology.

[106]  S. H. Lillie,et al.  Reserve carbohydrate metabolism in Saccharomyces cerevisiae: responses to nutrient limitation , 1980, Journal of bacteriology.

[107]  I. D. de Castro,et al.  Physiological role of yeasts NAD(P)+ and NADP+-linked aldehyde dehydrogenases. , 1977, Revista espanola de fisiologia.

[108]  D. Wilken,et al.  Ketopantoyl lactone and ketopantoic acid reductases. Characterization of the reactions and purification of two forms of ketopantoyl lactone reductase. , 1974, The Journal of biological chemistry.

[109]  H. Schulz,et al.  Purification and Properties of a Diacetyl Reductase from Escherichia coli , 1974, Journal of bacteriology.

[110]  J. Gancedo,et al.  Reduced pyridine-nucleotides balance in glucose-growing Saccharomyces cerevisiae. , 1973, European journal of biochemistry.

[111]  J. Gancedo,et al.  Contribution of the pentose-phosphate pathway to glucose metabolism in Saccharomyces cerevisiae: A critical analysis on the use of labelled glucose , 1973 .

[112]  E. Schweizer,et al.  Gene linkage and gene-enzyme relations in the fatty-acid-synthetase system of Saccharomyces cerevisiae. , 1972, European journal of biochemistry.

[113]  L. Ernster,et al.  Factors governing the kinetics and steady state of the mitochondrial nicotinamide nucleotide transhydrogenase system. , 1970, European journal of biochemistry.

[114]  C. Bernofsky,et al.  Activation of mitochondrial DPN kinase from yeast , 1970, FEBS letters.

[115]  M. Losada,et al.  Regulation and function of pyruvate kinase and malate enzyme in yeast. , 1967, European journal of biochemistry.

[116]  F. S. Stekhoven.  Studies on yeast mitochondria. 1. Existence of three phosphorylation sites along the respiratory chain of isolated yeast mitochondria. , 1966, Archives of biochemistry and biophysics.

[117]  V. Prelog.  Specification of the stereospecificity of some oxido-reductases by diamond lattice sections , 1964 .