An efficient biotransformation of dialkyl esters of 2-oxoglutaric acid by Rhodotorula minuta whole cells

Whole cells of the yeast Rhodotorula minuta were used in the biotransformation of dialkyl esters of 2-oxoglutaric acid. Almost 100% of conversion with 97–98% of enantiomeric excess of the (S) form of 2-hydroxydiesters was obtained through an enantioselective reduction of dimethyl and diethyl 2-oxoglutarate. When longer alkoxy chain 2-oxoglutarates were used as substrates, the corresponding 4-hydroxybutyric esters were obtained, suggesting a combination process including hydrolysis, decarboxylation and reduction. The cells showed a remarkable high productivity: high conversion and enantiomeric excess were obtained at 2 g wet weight mmol−1 substrate.

[1]  Jian‐He Xu,et al.  Asymmetric Reduction of Ketones by Employing Rhodotorula sp. AS2.2241 and Synthesis of the β-Blocker (R)-Nifenalol (XVI). , 2006 .

[2]  Jian‐He Xu,et al.  Asymmetric reduction of ketones by employing Rhodotorula sp. AS2.2241 and synthesis of the β-blocker (R)-nifenalol , 2006 .

[3]  Dunming Zhu,et al.  A recombinant ketoreductase tool-box. Assessing the substrate selectivity and stereoselectivity toward the reduction of β-ketoesters , 2006 .

[4]  A. Hochkoeppler,et al.  Use of Rhodotorula minuta Live Cells Hosted in Water‐in‐Oil Macroemulsion for Biotrasformation Reaction , 2006, Biotechnology progress.

[5]  F. Toste,et al.  Vanadium-Catalyzed Asymmetric Oxidation of α-Hydroxy Esters Using Molecular Oxygen as Stoichiometric Oxidant. , 2005 .

[6]  E. Żymańczyk-Duda,et al.  Stereochemical control of biocatalytic asymmetric reduction of diethyl 2-oxopropylphosphonate employing yeasts , 2005 .

[7]  A. Chadha,et al.  Asymmetric Reduction of Alkyl 2‐Oxo‐4‐arylbutanoates and ‐but‐3‐enoates by Candida parapsilosis ATCC 7330: Assignment of the Absolute Configuration of Ethyl 2‐Hydroxy‐4‐(p‐methylphenyl)but‐3‐enoate by 1H NMR. , 2005 .

[8]  W. Reynolds,et al.  Stemodane skeletal rearrangement: chemistry and microbial transformation. , 2005, Phytochemistry.

[9]  A. Baiker.  Reflections on Chiral Metal Surfaces and Their Potential for Catalysis , 2005 .

[10]  F. Toste,et al.  Vanadium-catalyzed asymmetric oxidation of alpha-hydroxy esters using molecular oxygen as stoichiometric oxidant. , 2005, Journal of the American Chemical Society.

[11]  I. Alfonso,et al.  Enantioselective enzymatic desymmetrizations in organic synthesis. , 2005, Chemical reviews.

[12]  S. Moreno,et al.  Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid , 2004 .

[13]  A. Sewell,et al.  Systematic investigation of Saccharomyces cerevisiae enzymes catalyzing carbonyl reductions. , 2004, Journal of the American Chemical Society.

[14]  T. Matsuda,et al.  Recent developments in asymmetric reduction of ketones with biocatalysts , 2003 .

[15]  P. Fernandes,et al.  Microbial conversion of steroid compounds: recent developments , 2003 .

[16]  B. Kendrick.  Ainsworth & Bisby's Dictionary of the Fungi, 9th edition, P.M. Kirk, P.F. Cannon, J.C. David, J.A. Stalpers (Eds.). CABI Publishing, Wallingford, UK (2001), Pp. 655. ISBN 0-85199-377-X (Hard cover). Price £49.95; US $90. , 2003 .

[17]  M. North.  Synthesis and applications of non-racemic cyanohydrins , 2003 .

[18]  P. Ramachandran,et al.  Selective Reductions. 59. Effective Intramolecular Asymmetric Reductions of α-, β-, and γ-Keto Acids with Diisopinocampheylborane and Intermolecular Asymmetric Reductions of the Corresponding Esters with B-Chlorodiisopinocampheylborane , 2002 .

[19]  N. Bruce,et al.  Microbial transformation of alkaloids. , 2002, Current opinion in microbiology.

[20]  S. Moreno,et al.  Chemo- and stereoselective reduction of β-keto esters by spores and various morphological forms of Mucor rouxii , 2002 .

[21]  Ramesh N. Patel,et al.  Enantioselective microbial reduction of 2-oxo-2-(1′,2′,3′,4′-tetrahydro-1′,1′,4′,4′-tetramethyl-6′-naphthalenyl)acetic acid and its ethyl ester , 2002 .

[22]  Kaoru Nakamura,et al.  Stereocontrolled reduction of α-keto esters with thermophilic actinomycete, Streptomyces thermocyaneoviolaceus IFO 14271 , 2000 .

[23]  M. Mihovilovic,et al.  Baker's Yeast-Mediated Reductions of alpha-Keto Esters and an alpha-Keto-beta-Lactam. Two Routes to the Paclitaxel Side Chain. , 1999, The Journal of organic chemistry.

[24]  P. Nitti,et al.  ENANTIOMERICALLY PURE TETRAHYDRO-5-OXO-2-FURANCARBOXYLIC ESTERS FROM DIALKYL 2-OXOGLUTARATES , 1999 .

[25]  T. Akasaka,et al.  Stereochemical Control in Microbial Reduction. Part 31. Reduction of Alkyl 2‐Oxo‐4‐arylbutyrates by Baker′s Yeast under Selected Reaction Conditions. , 1998 .

[26]  T. Akasaka,et al.  Stereochemical control in microbial reduction. Part 31: Reduction of alkyl 2-oxo-4-arylbutyrates by baker's yeast under selected reaction conditions , 1998 .

[27]  Kaoru Nakamura,et al.  Stereochemical Control in Microbial Reduction. 30. Reduction of Alkyl 2-Oxo-4-phenylbutyrate as Precursors of Angiotensin Converting Enzyme (ACE) Inhibitors , 1998 .

[28]  H. Veschambre,et al.  Regioselective or enantiogenic electrochemical and microbial reductions of 1,2-diketones , 1998 .

[29]  C. Richard,et al.  Synthesis of Trimegestone: The First Industrial Application of Bakers′ Yeast Mediated Reduction of a Ketone. , 1997 .

[30]  C. Richard,et al.  Synthesis of Trimegestone: The First Industrial Application of Bakers' Yeast Mediated Reduction of a Ketone , 1997 .

[31]  Kaoru Nakamura,et al.  Mechanistic study for stereochemical control of microbial reduction of α-keto esters in an organic solvent , 1995 .

[32]  Kaoru Nakamura.  Stereochemical Control in Microbial Reduction , 1991 .

[33]  David L. Hawksworth,et al.  Ainsworth & Bisby's Dictionary of the Fungi , 1972 .