Synthesis of the (4R, 5R)-Isomer of 5-Hydroxy-6-phenyl-4-hexanolide, a Lateral Root-inducing Substance Isolated from Erwinia quercina
スポンサーリンク
概要
- 論文の詳細を見る
Lipase-catalyzed enantioselective lactonization of racemic methyl 6-phenyl-4-hydroxy-5-hexynoate worked well to afford (R)-6-phenyl-5-hexyn-4-olide (42% yield, 81% e.e.). The e.e. of the product was enhanced to 97% by the repetition of enzymatic reaction. From this lactone, (4R, 5R)-isomer of 5-hydroxy-6-phenyl-4-hexanolide, a lateal root inducing substance from Erwinia quercina was synthesized via a selective epoxidation of the intermediate and subsequent hydrogenolysis as the keystep.
- 社団法人日本農芸化学会の論文
- 1992-01-23
著者
-
Ohta Hiromichi
Department Of Chemistry Faculty Of Science And Technology Keio University
-
SUGAI Takeshi
Department of Chemistry, Faculty of Science and Technology, Keio University
-
Ohta Hiromichi
Department Of Applied Chemistry School Of Engineering Nagoya University
-
Sugai Takeshi
Department Of Agricultural Chemistry The University Of Tokyo
-
NOGUCHI Hajime
Department of Chemistry, Keio University
-
Noguchi Hajime
Department Of Chemistry Keio University
関連論文
- Electrical Resistivity Measurements of Pd_Cu_Ni_P_ Alloy in Supercooled Liquid and Liquid State
- Thermal Diffusivities and Conductivities of Molten Germanium and Silicon
- Measurement of Thermal Diffusivity of Steels at Elevated Temperature by a Laser Flash Method
- A New Double Coupling System : Synthesis of Citronellyl Acetate via Transacetylation to Citronellol from Acetyl Coenzyme A Produced from Glucose and Free Fatty Acids(Microbiology & Fermentation Technology)
- Solution Structure of the SH2 Domain of Grb2 / Ash Complexed with EGF Receptor-Derived Phosphotyrosine-Containing Peptide
- MK800-62F1, a New Inhibitor of Apoptotic Cell Death, from Streptomyces diastatochromogenes MK800-62F1 : II. Structure Elucidation
- Improved Conditions for the Production and Characterization of 1-Arylpropane-1,2-diols and Related Compounds
- Improved Enzymatic Procedure for a Preparative-Scale Synthesis of Sialic Acid and KDN
- Access to Enantiomerically Pure Intermediates for (-) -Geosmin Synthesis Starting from (4aS, 5S) -4, 4a, 5, 6, 7, 8-Hexahydro-5-hydroxy-4a-methyl-naphthalen-2 (3H) -one(Organic Chemistry)
- Preparation of Optically Active α-Hydroxy Acid Derivatives by Microbial Hydrolysis of Cyanohydrins and Its Application to the Synthesis of (R)-4-Dodecanolide(Organic Chemistry)
- Biochemical Preparation of Optically Active 4-Hydroxy-β-ionone and Its Transformation to (S)-6-Hydroxy-α-ionone(Organic Chemistry)
- Regio- and Enantio-selective Reduction of α,γ-Diketones by Fermenting Bakers' Yeast(Organic Chemistry)
- Reductive C_2-Homologation of Substituted Benzaldehydes by Fermenting Baker's Yeast(Organic Chemistry)
- Synthesis of Regioselectively Protected Forms of Cytidine Based on Enzyme-catalyzed Deacetylation as the Key Step
- Degradation of Derivatives of N-Acetyl-D-glucosamine by Rhodococcus rhodochrous IFO 15564 : Substrate Specificity and Its Application to the Synthesis of Allyl α-N-Acetyl-D-glucosaminide
- A Chemo-Enzymatic Synthesis of _D-Allosamine Derivatives from Tri-O-acetyl-_D-glucal
- Efficient Route to (S)-Azetidine-2-carboxylic Acid
- Preparation of Methyl Ursodeoxycholate in an Interface Bioreactor : Use of a Mixed Solvent System to Increase the Solubilities of Substrate and Product
- Synthesis of Citronellyl Acetate via a Transacetylation to Citronellol from Acetyl Coenzyme A Produced from Glucose and Acetate in Growing Yeasts
- Preparation of Methyl Ursodeoxycholate via Microbial Reduction of Methyl 7-Ketolithocholate in an Anaerobic Interface Bioreactor
- Synthesis of Methyl Ursodeoxycholate via Microbial Reduction of Methyl 7-Ketolithocholate with Eubacterium aerofaciens JCM 7790 Grown on Two Kinds of Carbon and Hydride Sources, Glucose and Mannitol
- Syntheses of Optically Active Citronellol, Citronellal, and Citronellic Acid by Microbial Oxidation and Double Coupling System in an Interface Bioreactor
- Synthesis of (Rc,Ss)-1,1,1-Trifluoro-3-(p-tolylsulfinyl)-2-propanol by an Asymmaaaaetric Reduction with a Test, Yamadazyma farinosa, as a Key-step
- Preparative-scale Enzyme-catalyzed Synthesis of (R)-α-Fluorophenylacetic Acid
- Production of Ethyl (R)-2-Hydroxy-4-phenylbutanoate via Reduction of Ethyl 2-Oxo-4-phenylbutanoate in an Interface Bioreactor
- Cysteine188 Revealed as Being Critical for the Enzyme Activity of Arylmalonate Decarboxylase by Site-Directed Mutagenesis
- Biocatalysis in Organic Synthesis : The Use of Nitrile- and Amide-hydrolyzing Microorganisms
- Pivotal Role of (E)-3-Carbamoyl-1-propenylboronic Acid in the Combination of Suzuki-Miyaura Coupling and Enzyme Reactions : Synthesis of (3E, 5E)- and (3E, 5Z)-6-Phenyl-3, 5-hexadienoic Acid
- Preparation of Sulfur-Containing Optically Active Secondary Alcohols Based on Pichia farinosa-Catalyzed anti-Prelog-Rule Reduction
- Efficient Lipase-catalyzed Preparation of Long-chain Fatty Acid Esters of Bile Acids: Biological Activity and Synthetic Application of the products
- Action of Nitrile Hydratase from Rhodococcus rhodochrous IFO 15564 on Derivatives of 2,5-Anhydro-D-allononitrile
- Preparation and Thermoelectric Properties of Na_xCoO_2/Co_3O_4 Layered Nano-Composite
- Thermoelectric Properties of(ZnO)5In2O3 Thin Films Prepared by r.f.Sputtering Method (特集 熱電変換材料)
- A Complementary Flight Control System for Backside Landing
- Low Speed Turning Flight Path Control of a STOL Aircraft
- Enantioselective Oxidation of Sulfinic Acid Esters with the Aid of a Microorganism
- Enzymatic Preparation of Glycerol-related Chiral Pool Possessing tert-Alkoxy Group
- A Novel Enzymatic Decarboxylation Proceeds via a Thiol Ester Intermediate
- Measurement of Physical Properties of Slag Formed around the Raceway in the Working Blast furnace
- Usefulness of the Perineum Pusher in Performing Rectal Procedures
- On the Conformation of the Substrate Binding to the Active Site during the Course of Enzymatic Decarboxylation
- The Mode of Substrate-Recognition Mechanism of Arylmalonate Decarboxylase
- Direct Observation of Thiol Ester Formation between an Enzyme and an Active Site Directed Inhibitor by FT-IR
- Synthesis of (S)-Ibuprofen via Enantioselective Degradation of Racemic Ibuprofen with an Isolated Yeast, Trichosporon cutaneum KPY 30802, in an Interface Bioreactor
- Enantioselective Oxidation of Racemic Citronellol with an Interface Bioreactor
- Production of (S)-Citronellic Acid and (R)-Citronellol with an Interface Bioreactor
- Purification and Gene Cloning of an Enantioselective Thioesterification Enzyme from Brevibacterium ketoglutamicum KU1073, a Deracemization Bacterium of 2-(4-Chlorophenoxy)propanoic Acid
- Syntheses of Highly Oxygen-functionalized Derivatives of Dihydrodihydroxyphthalic Acid in Enantiomerically Enriched Forms
- Biodesulfurization of Dibenzothiophene with Rhodococcus erythropolis ATCC 53968 and Its Mutant in an Interface Bioreactor(ENVIRONMENTAL BIOTECHNOLOGY)
- Biocatalytic Preparation of (R) - (-) -4- (Phenylthio) -2-butanol and (R) - (-) -4- (Phenylsulfonyl) -2-butanol by the Sequential Use of Pichia farinosa and Rhodococcus rhodochrous
- Purification and Characterization of Arylmalonate Decarboxylase from Achromobacter sp. KU1311(ENZYMOLOGY, PROTEIN ENGINEERING, AND ENZYME TECHNOLOGY)
- Stereochemistry of Decarboxylation of Arylmalonate Catalyzed by Mutant Enzymes
- The Aldol Type Reaction Catalyzed by Arylmalonate Decarboxylase : A Decarboxylase can Catalyze an Entirely Different Reaction, Aldol Reaction
- Synthesis of (4aR, 10aS)-(-)-8-Methoxy-1, 1, 4a-trimethyl-2-oxo-1, 2, 3, 4, 4a, 9, 10, 10a-octahydrophenanthrene, an Optically Active Intermediate for the Synthesis of Diterpenes(Organic Chemistry)
- Mechanistic Studies on Nitrosation-Deaminocyclization of Mono-Carbamoylated Vicinal Amino Alcohols and Diols : A New Preparative In Situ Formation of Ethanediazo Hydroxide for the Ethylation of Carboxylates under Mild Conditions
- Enzymatic Preparation of Ethyl (S)-3-Hydroxybutanoate with a High Enantiomeric Excess(Organic Chemistry)
- Synthesis of the (4R, 5R)-Isomer of 5-Hydroxy-6-phenyl-4-hexanolide, a Lateral Root-inducing Substance Isolated from Erwinia quercina
- Biochemical Preparation of (R)-Sulcatol(Organic Chemistry)
- Short-Step and Scalable Synthesis of (±)-Cytoxazone
- Lipase-Catalyzed Kinetic Resolution of 2-Hydroxyhexadecanoic Acid and Its Esters(Organic Chemistry)
- A Simple Preparation of (R)-2-Hydroxy-4-phenyl-butanoic Acid(Organic Chemistry)
- Interactions of Plasma Proteins and Polymeric Materials
- Purification and Gene Cloning of an Enantioselective Thioesterification Enzyme from Brevibacterium ketoglutamicum KU1073, a Deracemization Bacterium of 2-(4-Chlorophenoxy)propanoic Acid
- Enzymatic Synthesis of (R)-Flurbiprofen
- Biochemical Reduction of 3-Oxoalkanoic Esters by a Bottom-fermentation Yeast, Saccharomyces cerevisiae IFO 0565
- Asymmetric Hydrolysis of 1-Cyanoalkyl Acetates(Organic Chemistry)
- Asymmetric Hydrolysis of Aryloxyacetaldehyde Cyanohydrin Acetates
- Microbial Transformation on Interface between Hydrophilic Carriers and Hydrophobic Organic Solvents
- Double Coupling of Acetyl Coenzyma A Production and Microbial Esterification with Alcohol Acetyltransferase in an Interface Bioreactor
- Coupling of Fermentation and Esterification : Microbial Esterification of Decanoic Acid with Ethanol Produced via Fermentation
- Alleviation of Toxicity of Poisonous Organic Compounds on Hydrophilic Carrier/Hydrophobic Organic Solvent Interface
- Reduction of Acyl Enolates of α-Substituted β-Keto Esters by Bakers' Yeast(Organic Chemistry)
- Interface Bioreactor Packed with Synthetic Polymer Pad : Application to Hydrolysis of Neat 2-Ethylhexyl Acetate
- Both Enantiomers of N-Boc-indoline-2-carboxylic Esters
- An Approach to Anthracycline Synthetic Intermediate from Novel Glycerol-related Chiral Pool
- An Expeditious Route to N-Acetyl-D-galactosamine from N-Acetyl-D-glucosamine Based on the Selective Protection of Hydroxy Groups
- Estimation of Heat Transfer of a Front-heating Front-detection Laser Flash Method Measuring Thermal Conductivity for Silicate Melts at High Temperatures
- Purification and Characterization of the Alcohol Dehydrogenase with a Broad Substrate Specificity Originated from 2-Phenylethanol-Assimilating Brevibacterium sp. KU 1309(ENZYMOLOGY, PROTEIN ENGINEERING, AND ENZYME TECHNOLOGY)
- A Chemo-Enzymatic Expeditious Route to Racemic Dihexanoyl (2R*,3R*,4R*)-Dehydroxymethylepoxyquinomycin (DHMEQ), the Precursor for Lipase-Catalyzed Synthesis of the Potent Nuclear Factor-κB Inhibitor, (2S,3S,4S)-DHMEQ
- Microbial Hydrogenation of Nitroolefins
- Stereoselective Oxidation of β-Methyl-sec-alcohols and α-Methylketones by Corynebacterium equi IFO 3730
- Microbial Hydrolysis of Substituted Mandelonitrile Acetates and Its Application to the Synthesis of Optically Active Physiological Ethanolamines
- Oxidation of sec-Alcohols to the Corresponding Ketones by Corynebacterium equfi
- Structural Properties of Brazil Nut 11Globulin, Excelsin
- Synthesis of (S)-2-Hydroxy-β-ionone, Employing (S)-3-Hydroxy-2, 2-dimethylcyclohexanone as the Chiral Starting Material
- Preparation of Optically Active Secondary Alcohols Related to Synthetic Pyrethroids by Microbial Asymmetric Hydrolysis of the Corresponding Acetates
- Oxidation of Allylic Sulfides with Corynebacterium equi
- Synthesis of Both the Enantiomers of 4-Dodecanolide, a Defensive Secretion of Rove Beetles
- Microbial Oxidation of Cyclic Alcohols to the Corresponding Ketones
- Microbial Reduction of 1, 2-Diketones to Optically Active α-Hydroxyketones
- Microbial Oxidation of Alkyl Aryl Sulfides to the Corresponding Optically Active Sulfoxides
- Both Enantiomers of 8-Hydroxyhexadecanoic Acid Inhibit the Spore Germination of Lygodium japonicum
- Enzyme-Mediated Enantioselective Protonation to Enolates in an Aqueous Medium
- Solution Structure of the SH2 Domain of Grb2/Ash Complexed with EGF Receptor-Derived Phosphotyrosine-Containing Peptide.
- Synthesis of Okicamelliaside, a Glucoside of Ellagic Acid with Potent Anti-Degranulation Activity