Stereochemical Outcome of the Biocatalysed Reduction of Activated Tetrasubstituted Olefins by Old Yellow Enzymes 1–3

The ene-reductase-mediated reactions of (E)- and (Z)-stereoisomers of tetrasubstituted activated alkenes were performed by means of isolated old yellow enzymes (OYEs) 1–3. The comprehension of the resulting data required a careful analysis of the stereochemical course of this kind of reaction. The investigation of the bioreduction of tetrasubstituted alkenes allowed us to appreciate the contribution of several factors (configuration of the starting alkene, mechanism of hydrogen addition, substrate binding mode) to the overall stereochemistry of the reaction.

[1]  F. Parmeggiani,et al.  Biocatalyzed Enantioselective Reduction of Activated C=C Bonds: Synthesis of Enantiomerically Enriched α-Halo-β-arylpropionic Acids , 2011 .

[2]  K. Zangger,et al.  Stereo‐Controlled Asymmetric Bioreduction of α,β‐Dehydroamino Acid Derivatives , 2011 .

[3]  H. Meyer Sustainability and Biotechnology , 2011 .

[4]  Kurt Faber,et al.  Asymmetric Synthesis of (R)‐3‐Hydroxy‐2‐methylpropanoate (‘Roche Ester’) and Derivatives via Biocatalytic CC‐Bond Reduction , 2010 .

[5]  E. Brenna,et al.  Stereochemical Analysis of the Enzymic Reduction of the Double Bond of α-and β-Substituted Nitrostyrenes and α-Ethoxycinnamaldehyde through Deuterium Labelling Experiments , 2010 .

[6]  S. M. Glueck,et al.  Bioreduction of alpha-methylcinnamaldehyde derivatives: chemo-enzymatic asymmetric synthesis of Lilial and Helional. , 2010, Dalton Transactions.

[7]  N. Scrutton,et al.  Biocatalytic Reductions and Chemical Versatility of the Old Yellow Enzyme Family of Flavoprotein Oxidoreductases , 2010 .

[8]  F. Parmeggiani,et al.  New stereospecific synthesis of Tesaglitazar and Navaglitazar precursors , 2009 .

[9]  C. Fuganti,et al.  Stereochemical Course of Baker's Yeast Mediated Reduction of the Tri‐ and Tetrasubstituted Double Bonds of Substituted Cinnamaldehydes , 2009 .

[10]  J. Stewart,et al.  Site-saturation mutagenesis of tryptophan 116 of Saccharomyces pastorianus old yellow enzyme uncovers stereocomplementary variants. , 2009, Journal of the American Chemical Society.

[11]  K. Fisher,et al.  Structure-Based Insight into the Asymmetric Bioreduction of the C=C Double Bond of alpha,beta-Unsaturated Nitroalkenes by Pentaerythritol Tetranitrate Reductase. , 2008, Advanced synthesis & catalysis.

[12]  B. Hauer,et al.  Asymmetric Bioreduction of Activated C=C Bonds Using Zymomonas mobilis NCR Enoate Reductase and Old Yellow Enzymes OYE 1–3 from Yeasts , 2008 .

[13]  P. Macheroux,et al.  Stereocomplementary bioreduction of alpha,beta-unsaturated dicarboxylic acids and dimethyl esters using enoate reductases: enzyme- and substrate-based stereocontrol. , 2007, Organic letters.

[14]  B. Hauer,et al.  Asymmetric alkene reduction by yeast old yellow enzymes and by a novel Zymomonas mobilis reductase , 2007, Biotechnology and bioengineering.

[15]  Bernhard Hauer,et al.  Asymmetric bioreduction of activated C=C bonds using enoate reductases from the old yellow enzyme family. , 2007, Current opinion in chemical biology.

[16]  C. Fuganti,et al.  Stereochemical aspects of the bioreduction of the conjugated double bond of perillaldehyde , 2004 .

[17]  N. Scrutton,et al.  Biotransformation of Explosives by the Old Yellow Enzyme Family of Flavoproteins , 2004, Applied and Environmental Microbiology.

[18]  N. Bruce,et al.  'New uses for an Old Enzyme'--the Old Yellow Enzyme family of flavoenzymes. , 2002, Microbiology.

[19]  N. Tokitoh,et al.  Asymmetric reduction of nitroalkenes with baker's yeast , 2001 .

[20]  P. Karplus,et al.  On the Active Site of Old Yellow Enzyme , 1998, The Journal of Biological Chemistry.

[21]  V. Massey,et al.  The Oxidative Half-reaction of Old Yellow Enzyme , 1998, The Journal of Biological Chemistry.

[22]  S. Servi,et al.  Extractive biocatalysis: A powerful tool in selectivity control in yeast biotransformations , 1998 .

[23]  R. Rallo,et al.  Stereochemistry of the double bond saturation in the formation in baker's yeast of 4-(4-hydroxyphenyl)-2-butanone (raspberry ketone) , 1996 .

[24]  S. Servi,et al.  Baker's yeast reduction of arylidenecycloalkanones , 1995 .

[25]  S. Chakraborty,et al.  A New Old Yellow Enzyme of Saccharomyces cerevisiae(*) , 1995, The Journal of Biological Chemistry.

[26]  P. Karplus,et al.  Old yellow enzyme at 2 A resolution: overall structure, ligand binding, and comparison with related flavoproteins. , 1994, Structure.

[27]  R. Rallo,et al.  Stereochemistry of the baker's yeast mediated reduction of the CC bond of (Z)- and (E)-5-benzoyloxyhex-3-en-2-one , 1994 .

[28]  A. Mele,et al.  On the mode of baker's yeast reduction of C-7 --- C-10 2-alken-4-olides , 1993 .

[29]  D. Thiele,et al.  Old Yellow Enzyme. The discovery of multiple isozymes and a family of related proteins. , 1993, The Journal of biological chemistry.

[30]  C. Fuganti,et al.  Stereochemistry of the yeast - mediated conversion of delta 2 - decenolide into delta decanolide , 1992 .

[31]  D. Thiele,et al.  The cloning and expression of a gene encoding Old Yellow Enzyme from Saccharomyces carlsbergensis. , 1991, The Journal of biological chemistry.

[32]  A. Mele,et al.  The mode of bakers' yeast transformation of 3-chloropropiophenone and related ketones. Synthesis of (2S)-[2-2H]propiophenone, (R)-fluoxetine, and (R)- and (S)-fenfluramine , 1991 .

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

[34]  C. Fuganti Baker's yeast mediated synthesis of natural products , 1990 .

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