Stereochemical control in microbial reduction. 8. Stereochemical control in microbial reduction of .BETA.-keto esters.
スポンサーリンク
概要
- 論文の詳細を見る
Stereochemistry of the reduction of β-keto esters with bakers' yeast is controlled by the addition of a certain α,β-unsaturated carbonyl compound (or its reduced form). Glucose also exerts the same effect. The additives tend to shift the stereochemistry of the reduction toward the production of D-hydroxy ester. Namely, methyl 3-oxopentanoate and ethyl 3-oxo-6-heptenoate were reduced to the corresponding D-hydroxy esters with excellent stereoselectivities and chemical yields. The enones are supposed to inhibit the enzymes that produce the L-hydroxy ester, whereas glucose plays a role to activate the enzymes that produce the D-hydroxy ester.
- 公益社団法人 日本化学会の論文
著者
-
Kawai Yasushi
Institute For Chemical Research Kyoto University
-
Ohno Atsuyoshi
Institute For Chemical Research Kyoto Univ.
-
Oka Shinzaburo
Institute For Chemical Research Kyoto University
-
Nakamura Kaoru
Department of Chemistry, Shiga University of Medical Science
関連論文
- Asymmetric Reduction of α-Keto Esters and α-Diketones with a Bakers' Yeast Keto Ester Reductase
- Amino Acid Sequence and Characterization of Aldo-keto Reductase from Bakers' Yeast
- N-Acetylcysteine Modifies cis-Dichlorodiammineplatinum-induced Effects in Bladder Cancer Cells
- The Clinical Effectiveness of Laser-Lithotripsy for Ureteral Calculi with an Automatic Stone Detection System
- Efficient Synthesis, Structure, and Redox Reactions of 1,4,6,9-Tetraisopropylchalcogenanthrenes
- Synthesis of New Pentathiepin and Dithiatriselenepin Fused to Ferrocene via Dithiametallacycles
- Design of Reversible Low Redox Potential Systems Using Five-Membered Trichalcogenaheterocycles Containing Heavy Chalcogens ; Sulfur, Selenium, and Tellurium
- Preparation of Functionalized Thianthrenes and Their Higher Related Compounds by Photolysis of Benzotrithiole Derivatives
- Generation and Detection of a Dithia Dication Derived from 4,9-Diethyl-[1,4]dihydrodithiino[5,6-f]benzotrithiole 5-Oxide and Its Disproportionation
- Preparation and Conformational Analysis of 6,10-Diethyl[1,2,3]trithiolo-[4,5-h]benzopentathiepin Monoxides : Isolation and Optical Properties of Chiral Benzopentathiepin Derivatives
- First Preparation and Structural Determination of Optically Pure Cyclic Polysulfides, 6, 10-Diethyl Trithiolo[h]benzopentathiepin Monooxides
- Synthesis and Unique Packing Structure by X-Ray Analysis of New Types of Stable Trithioles Bound to Fused Aromatic Systems
- Synthesis, Structure, and Oxidation of Novel 4,7-Disubstituted Benzotrithioles. Formation and Characterization of Radical Cations with 11πElectron Framework
- Long-term results of three different minimally invasive therapies for lower urinary tract symptoms due to benign prostatic hyperplasia : Comparison at a single institute
- Differential Diagnosis of Primary Benign and Malignant Retroperitoneal Tumors
- TREATMENT OF BENIGN PROSTATIC HYPERPLASIA WITH HIGH INTENSITY FOCUSED ULTRASOUND: AN INITIAL CLINICAL TRIAL IN JAPAN WITH MAGNETIC RESONANCE IMAGING OF THE TREATED AREA
- High Intensity Focused Ultrasound for Benign Prostatic Hyperplasia; A 6-month Follow-up
- Purification and Characterization of α-Keto Ester Reductases from Bakers' Yeast
- Synthesis, Structure and Properties of [7] Heterohelicenes Possessing Phenolic Hydroxy Functions
- Reactivities of Stable Rotamers. XLI. Reactions of 1-(9-Fluorenyl)-2-(1-methylethenyl)naphthalene Rotamers with Chalcogenyl Halides and Observation of Coloration During the Reaction of Methanesulfenyl Chloride and the ap-Rotamer
- Strip biopsy of superficial bladder tumors using an electrosurgical snare
- Establishment of a Human Cell Line Secreting Neuron-specific Enolase from a Primitive Neuroectodermal Tumor of the Retroperitoneal Cavity
- Influence of Extrusion on the Physiological Effects of Brans in Rats(Food & Nutrition)
- Chemistry of Zerumbone. 2. Regulation of Ring Bond Cleavage and Unique Antibacterial Activities of Zerumbone Derivatives(Organic Chemistry)
- Stereochemical Control in Microbial Reduction. 30. Reduction of Alkyl 2-Oxo-4-phenylbutyrate as Precursors of Angiotensin Converting Enzyme (ACE) Inhibitors
- Conformational Effect (Induced-Fit) on Catalytic Activity of α-Chymotrypsin
- Stereochemical Control in Microbial Reduction. XXIX. Mechanism of Stereochemical Control with an Additive in the Diastereoselective Reduction by Geotrichum candidum
- Stereochemical Control in Microbial Reduction. XXV. Additives Controlling Diastereoselectivity in a Microbial Reduction of Ethyl 2-Methyl-3-oxobutanoate
- Stereoselective Preparation of (R)-4-Nitro-2-butanol and (R)-5-Nitro-2-pentanol Mediated by a Lipase(Organic Chemistry)
- PB124 DIASTEREOSELECTIVE SYNTHESIS OF 2-ALKYL-3-HYDROXYBUTANOATES, USEFUL CHIRAL SYNTHONS, BY MICROBES
- New Color Vision Tests to Evaluate Faulty Color Recognition
- A case of successful management of maternal septic shock with multiple organ failure following amniocentesis at midgestation
- Irreversibility of Single Electron Transfer Occurring from Trivalent Phosphorus Compounds to Iron (III) Complexes in the Presence of Ethanol
- Reaction of Trivalent Phosphorus Compounds with an Fe (III) Complex in the Presence of Alcohol. Single Electron Transfer Accompanied by a P-O Bond Formation
- Stereoelectronic Effects on the One-Electron Donor Reactivity of Trivalent Phosphorus Compounds. Experimental and Theoretical Investigations
- Stereochemical Control in Microbial Reduction. XXVIII. Asymmetric Reduction of α,β-Unsaturated Ketones with Bakers' Yeast
- NAD(P)^+-NAD(P)H Models. 87. Nonsteric Stereochemistry Controlled by a Carbonyl Dipole
- NAD(P)^+-NAD(P)H Models. 86. Nonsteric Stereochemistry in Hydride-Transfer to Sulfinylpyridinium Ion
- Reactivity of Cation Radicals Generated from Trivalent-Phosphorus Compounds in the Reaction with Methylviologen: Kinetic Analysis
- Stereospecific Electrochemical Oxidation of NAD(P)H Analogs Mediated by Radical Cation of Anilines
- Asymmetric Reduction of Butyl Pyruvate Catalyzed by Immobilized Glycerol Dehydrogenase in Organic-Aqueous Biphasic Media
- Usefulness of laparoscopy to find the distal vas deferens during vasovasostomy for a patient with iatrogenic injury of the vas deferens during inguinal herniorrhaphy
- The Catalytic Role of Iodide Ion / Iodine Couple in the Photo-Reduction of 10-Methylacridinium Ion with Diphenylphosphine Oxide
- PB23 NAD(P)H MODELS-A HIGHLY SELECTIVE REDUCING REAGENTS IN ORGANIC SYNTHESIS
- Novel Reaction of Selenobenzophenones with Alkyllithiums Leading to Symmetrical Olefins
- Exalted Resonance Effect in the Aryl-Assisted Solvolyses of 2-Aryl-2-(trifluoromethyl)ethyl m-Nitrobenzenesulfonates
- Stereoselection without Steric Effect but Controlled by Electronic Effect : Important Contribution of Ground State
- Lipase-Catalyzed Transesterification of Aryl-Substituted Alkanols in an Organic Solvent
- Stereoselective Synthesis of (±)-Isonitramine and (±)-Sibirine
- Effects of Casein and Soy-Protein on .ALPHA.-Linolenic Acid Metabolism in Rats.
- NAD(P)H-NAD(P)+models. 74. Entropy-controlled kinetics, stereochemistry, and tunneling effect.
- NAD(P)+-NAD(P)H models. 71. A convenient route to the synthesis of juvabione.
- Reduction by a model of NAD(P)H. XIV. Mechanistic consideration on the role of metal ion.
- A new, highly efficient, and simple procedure for the construction of medium-sized nitrogen heterocyclic ring system.
- Effect of catalyst on the oxygenation of styrene with BH4- and molecular oxygen.
- Charge-transfer intermediate in the reaction of thioketone with nucleophiles.
- NAD(P)+-NAD(P)H models. 65. Photochemical reductive desulfonylation of .BETA.-keto sulfones with Hantzsch ester.
- NAD(P)+-NAD(P)H models. 59 1,2- Versus 1,4-reduction of .BETA.,.GAMMA.-unsaturated .ALPHA.-keto ester.
- Stereochemical control in microbial reduction. Part 7. Enantioselective reduction of 2-methyl-3-oxopropionate by bakers' yeast.
- Determination of the configuration of diastereoisomers of 2-alkyl-3-hydroxybutanoates with gas chromatography.
- NAD(P)+-NAD(P)H model. 54. Free radical mechanism for the reductive debromination of vic-dibromides to alkenes.
- Stereochemical control in microbial reduction. 12. (S)-4-nitro-2-butanol as a source to synthesize natural products.
- Reduction by a model of NAD(P)H. 34. Substituent effect on asymmetric reduction of trifluoroacetophenones.
- Reduction by a model of NAD(P)H. 32. Stereoselective reduction of camphoroquinone by a chiral NAD(P)H model.
- NAD(P)+-NAD(P)H models. 72. Isotope effects to prove the multi-step mechanism in the reduction with an NAD(P)H analog.
- NAD(P)H-NAD(P)+models. 73. Structure-stereochemistry relationship in the reaction of NAD analog.
- Reduction by a model of NAD(P)H. 35. Spectroscopic detection of charge-transfer intermediate.
- Stereochemistry of NAD(P)-coenzyme in the reaction catalyzed by glycerol dehydrogenase.
- Stereochemical control in microbial reduction. XV. Preparation of (2R, 3S)-2-allyl-3-hydroxybutanoate.
- NAD(P)+-NAD(P)H model. 63. Regioselective reduction of dienoic ketones and aldehydes with an NAD(P)H model on silica gel.
- Stereochemical control in microbial reduction. 8. Stereochemical control in microbial reduction of .BETA.-keto esters.
- The transition-metal catalyzed dehalogenation of aromatic halides by NaOH-alcohols. A facile method of destroying aromatic polyhalides.
- Stereochemical control in microbial reduction. 9. Diastereoselective reduction of 2-alkyl-3-oxobutanoate with bakers' yeast.
- A kinetic study of the reaction of 1-propyl-1,4-dihydronicotinamide with hexacyanoferrate(III).
- Reduction by a model of NAD(P)H. 36. First and direct evidence for the multi-step mechanism.
- Reaction of electrochemically generated radical anion of thioketone with alkylating agents.
- Monocyte-mediated cytotoxicity on bladder cancer cells in vitro and its implication in the treatment of bladder cancer patients with bacillus Calmette-Guerin.
- Stereochemical Control in Microbial Reduction. 18. Mechanism of Stereochemical Control in the Diastereoselective Reduction with Bakers' Yeast.