Synthesis of Decalin Type Chiral Synthons Base on Enzymatic Function
スポンサーリンク
概要
- 論文の詳細を見る
Enzymatic monobenzoylation of (±)-2-hydroxy-decahydro-5,5,8a-trimethyl-1-naphthalenemethanol derivatives (1-4) using vinyl benzoate in organic solvent gave the optically active diols (1-4) and monobenzoates (16-19). The enantiomeric excess (ee) of the enzymatic reaction products were found to be in the range of 11% to 49%. On the other hand, enzymatic hydrolysis of the acetoxybenzylidene acetal (±)-25d, e was found to give more than 90% ee of (10aS)-25d, e in moderate yield. Finally, the 90% ee of (10aS)-25e was converted to the 90% ee of the desired (8aS)-1.
- 公益社団法人日本薬学会の論文
- 2000-08-01
著者
-
Murakami Yukihisa
富山大学和漢医薬学総合研究所 複合薬物薬理学
-
AKITA Hiroyuki
School of Pharmaceutical Science, Toho University
-
Kato K
Toho Univ. Chiba Jpn
-
Kato K
Grad. Sch. Pharm. Sci. Nagoya City Univ.:okazaki Inst. Integ. Biosci. Natl. Inst. Natl. Sci.
-
Akita H
Toho Univ. Chiba Jpn
-
Akita Hiroyuki
School Of Pharmaceutical Science Toho University
-
NOZAWA Masako
School of Pharmaceutical Sciences, Toho University
-
Kato Keisuke
School Of Pharmaceutical Sciences Toho University
-
MURAKAMI Yumiko
School of Pharmaceutical Sciences, Toho University
-
NODA Keiko
School of Pharmaceutical Sciences, Toho University
-
TAMATSUKURI Ryouko
School of Pharmaceutical Sciences, Toho University
-
Noda K
School Of Pharmaceutical Sciences Toho University
-
Tamatsukuri Ryouko
School Of Pharmaceutical Sciences Toho University
-
Nozawa M
Graduate School Of Pharmaceutical Sciences Chiba University
-
野澤 雅子
School Of Pharmaceutical Science Toho University
-
Akita Hiroyuki
School Of Parmaceutical Sciences Toho University
-
Murakami Yumiko
School Of Pharmaceutical Sciences Toho University
-
Noda Keiko
School Of Pharmaceutical Sciences Toho University
-
Kato Keisuke
School Of Pharmaceutical Science Toho University
-
Kato Koichi
Okazaki Institute For Integrative Bioscience Institute For Molecular Science
関連論文
- Enhanced expression of BCL2/adenovirus EIB 19-kDa-interacting protein 3 mRNA, a candidate for intrinsic depression-related factor, and effects of imipramine in the frontal cortex of stressed mice
- Effects of Manganese Complexes of Curcumin and Diacetylcurcumin on Kainic Acid-Induced Neurotoxic Responses in the Rat Hippocampus(Pharmacology)
- Hypouricemic Effects of Acacetin and 4,5-O-Dicaffeoylquinic Acid Methyl Ester on Serum Uric Acid Levels in Potassium Oxonate-Pretreated Rats(Pharmacology)
- P-22 酵素機能を利用する高立体選択的キラルシントンの合成とその天然物合成への応用(ポスター発表の部)
- Reaction of Methyl 4,5-Epoxy-(2E)-pentenoate with Arenes. I. A Facile Synthesis of 4-Aryl-5-hydroxy-(2E)-pentenoate Derivatives
- 3P-015 MHC分子を構成するβ2ミクログロブリンのNMR構造解析(蛋白質・物性(3),第46回日本生物物理学会年会)
- 2P145 Redox-dependent conformational rearrangement of the substrate-binding domains of protein disulfide isomerase(33. Redox enzyme,Poster Session,Abstract,Meeting Program of EABS & BSJ 2006)
- 1P067 Structural and mutational analyses of curculin, a taste-modifying and sweet-tasting protein(2. Protein function (I),Poster Session,Abstract,Meeting Program of EABS & BSJ 2006)
- Fischer Indolization and Its Related Compounds. XIX. Syntheses of Ethyl 4-Methoxy- and Ethyl 5-Methoxy-1-phenyl-3H-benz [e] indole-2-carboxylates
- P-565 920 MHZ ULTRA-HIGH FIELD NMR ANALYSES OF PROTEINS AND GLYCOCONJUGATES
- Effects of Choto-san and Its Related Constituents on Endogenous Antioxidant Systems(Pharmacology)
- Antioxidant and Free Radical-Scavenging Activity of Choto-san and Its Related Constituents(Pharmacology)
- Fischer Indolization of Variously ortho-Substituted Phenylhydrazones (Fischer Indolization and Its Related Compounds. XXV)
- A NEW SYNTHESIS OF EUPOLAURAMINE FROM A BENZ [f] INDOLE DERIVATIVE
- Total Synthesis of (±)-, (-)-, and (+)-Oudemansin X
- Formal Syntheses of N-Trifluoroacetyl-L-acosamine and N-Trifluoroacetyl-L-daunosamine from an Achiral Precursor, Methyl Sorbate
- Synthesis of Ozonolysis Products of Myxothiazol
- Enzymatic Hydrolysis of meso(syn-syn)-1,3,5-Triacetoxy-2,4-dimethylpentane and Acetylation of meso(syn-syn)-3-Benzyloxy-2,4-dimethylpentane-1,5-diol by Lipase
- A Synthesis of (2R, 4'R, 8'R)-α-Tocopherol (Vitamin E) Side Chain
- Application of Combined Reagent Solution to the Oxidative Refolding of Recombinant Human Interleukin 6
- Disulfide Bond Formation in Refolding of Thermophilic Fungal Protein Disulfide Isomerase
- Effects of Mitragynine on cAMP Formation Mediated by δ-Opiate Receptors in NG108-15 Cells
- Anticonvulsant Activity of Paeonimetabolin-I Adducts Obtained by Incubation of Paeoniflorin and Thiol Compounds with Lactobacillus brevis
- Effects of Paeoniflorin Derivatives on Scopolamine-Induced Amnesia Using a Passive Avoidance Task in Mice; Structure-Activity Relationship
- Synthetic Studies of Indoles and Related Compounds. XXVII. A New Synthesis of Crenatine from Ethyl Indole-2-carboxylate
- Fischer Indolization and Its Related Compounds. XVIII. Formation of Four Unexpected Angular Benz [e] indoles on Fischer Indolization of Ethyl Phenylpyruvate 2-[(1,4-Dimethoxy-2-naphthyl) hydrazone]
- Synthetic Studies on Indoles and Related Compounds. XXVI. The Debenzylation of Protected Indole Nitrogen with Aluminum Chloride. (2)
- Permanent Occlusion of Bilateral Internal Carotid Arteries Produces Cognitive Deficits in Two Learning Behavior Tasks
- Synthesis of the Metabolites of 4-(2-Methyl-1H-imidazol-1-yl)-2,2-diphenylbutanamide (KRP-197/ONO-8025)
- 2P144 Four-domain arrangements of Thermophilic Fungal protein disulfide isomerase in redox state revealed by small-angle X-ray scattering(33. Redox enzyme,Poster Session,Abstract,Meeting Program of EABS & BSJ 2006)
- Possible Involvement of Signal Transducers and Activators of Transcription 3 System on Depression in the Model Mice Brain
- Chotosan Enhances Macrophage Colony-Stimulating Factor mRNA Expression in the Ischemic Rat Brain and C6Bu-1 Glioma Cells(Biochemistry)
- Chotosan, a Kampo Formula, Ameliorates Chronic Cerebral Hypoperfusion-Induced Deficits in Object Recognition Behaviors and Central Cholinergic Systems in Mice
- Preventive Effect of Chotosan, a Kampo Medicine, on Transient Ischemia-Induced Learning Deficit Is Mediated by Stimulation of Muscarinic M_1 But Not Nicotinic Receptor(Pharmacology)
- Social Isolation Stress-Induced Oxidative Damage in Mouse Brain and Its Modulation by Majonoside-R2, a Vietnamese Ginseng Saponin(Pharmacology)
- The Effects of Choto-san on the mRNA Expression of Alzheimer's Disease Related Factors in the Permanent Ischemic Rat Brain(Pharmacology)
- Evaluation of the Nitric Oxide Radical Scavenging Activity of Manganese Complexes of Curcumin and Its Derivative(Pharmacology)
- Berberine Exerts Neuroprotective Actions against in Vitro Ischemia-Induced Neuronal Cell Damage in Organotypic Hippocampal Slice Cultures : Involvement of B-Cell Lymphoma 2 Phosphorylation Suppression(Pharmacology)
- Cytoprotective and Cytotoxic Effects of Curcumin : Dual Action on H_2O_2-Induced Oxidative Cell Damage in NG108-15 Cells
- Protective effect of Choto-san and its related constituents on hydrogen peroxide-induced cell damage in NG108-15 cells
- Ameliorative Effects of Paeoniflorin, a Major Constituent of Peony Root, on Adenosine A_1 Receptor-Mediated Impairment of Passive Avoidance Performance and Long-Term Potentiation in the Hippocampus
- GTS-21, a Nicotinic Agonist, Attenuates Multiple Infarctions and Cognitive Deficit Caused by Permanent Occlusion of Bilateral Common Carotid Arteries in Rats
- Chronic Cerebral Hypoperfusion-Induced Neuropathological Changes in Rats
- Synthesis and Dual Antagonistic Activity against Thromboxane A_2 and Leukotriene D_4 of [4-[1-(Benzenesulfonamido)alkyl]phenyl]alkanoic Acid Derivatives
- Synthesis and Thromboxane A_2 Antagonistic Activity of [[1-Aryl(or Benzyl)-1-(benzenesulfonamide)methyl]phenyl]alkanoic Acid Derivatives
- Tacrine Improves Working Memory Deficit Caused by Permanent Occlusion of Bilateral Common Carotid Arteries in Rats
- Effect of Pilocarpine on Striatal Acetylcholine Release in Dopamine-Depleted Rats
- The Effect of Tulobuterol Tape on Histamine-Induced Bronchoconstriction in Conscious Guinea Pigs:Long Duration of Action
- Central Nervous System Effects of the Novel Antiallergic Agent HSR-609 and Typical Antiallergic Agents Using Behavioral and Electroencephalographic Analyses in Dogs
- Pharmacological Studies on the Novel Antiallergic Agent HSR-609: Its Effects on Behavior in Mice and Electroencephalograms in Rabbits
- A Wild-type Japanese Measles Virus Strain Inducing Predominant Early Down-regulation of CD46
- Molecular Cloning of a Complementary DNA for a Membrane Cofactor Protein (MCP, CD46)/Measles Virus Receptor on Vero Cells and Its Functional Characterization
- Fischer Indolization and Its Related Compounds. XXIV. Fischer Indolization of Ethyl Pyruvate 2-(2-Methoxyphenyl)phenylhydrazone
- Catalytic Properties for Naphthoquinones and Partial Primary Structure of Rabbit Heart Acetohexamide Reductase.
- Catalytic Properties for Naphthoquinones and Partial Primary Structure of Rabbit Heart Acetohexamide Reductase
- Carbonyl Reductase Purified from Rabbit Liver Is Not the Product of a Carbonyl Reductase Gene (RCBR5 or RCBR6)Cloned from the Rabbit Liver cDNA Libray.
- Carbonyl Reductase Purified from Rabbit Liver Is Not the Product of a Carbonyl Reductase Gene (RCBR5 or RCBR6) Cloned from the Rabbit Liver cDNA Library
- Characterization of Acetohexamide Reductases Purified from Rabbit Liver, Kidney, and Heart: Structural Requirements for Substrates and Inhibitors
- Purifiation and Catalytic Properties of a Novel Acetohexamide-Reducing Enzyme from Rabbit Heart
- Synthesis of Decalin Type Chiral Synthons Base on Enzymatic Function
- Enantioselective Synthesis of (2R, 4'R, 8'R)-α-Tocopherol (Vitamin E) Based on Enzymatic Function
- Stereoselective Reduction of Acetohexamide in Cytosol of Rabbit Liver
- Reaction of Methyl 4,5-Epoxy-(2E)-pentenoate with Arylcopper Reagents
- Chemoenzymatic Synthesis of Sacranosides A and B
- Chemoenzymatic Synthesis of Naturally Occurring Benzyl 6-O-Glycosyl-β-D-glucopyranosides
- Simple Synthesis of β-D-Glycopyranosides Using β-Glycosidase from Almonds
- Concise Syntheses of Coronarin A, Coronarin E, Austrochaparol and Pacovatinin A
- Facilitatory and Inhibitory Effects of Harmaline on the Tryptophan- Induced 5-Hydroxytryptamine Syndrome and Body Temperature Changes in Pargyline-Pretreated Rats
- Synthetic Study of Piericidins. II. Synthesis of Piericidin Analogues
- Synthetic Study of Piericidins. I. Synthesis of the Side Chain of Piercidin B_1
- In Vitro Refolding of Porcine Pepsin Immobilized on Agarose Beads
- γ-Herpesviruses and cellular signaling in AIDS-associated malignancies
- Effect of Herbimycin A on Tyrosine Kinase Receptors and Platelet Derived Growth Factor (PDGF)-Induced Signal Transduction
- Determination of the Absolute Stereostructure of seco-Macrosphelide E Produced by a Fungal Strain from a Sea Hare
- Concise Syntheses of Cystothiazoles A, C, D, and Melithiazol B
- Enzymatic Synthesis of (-)- and (+)-Acetoxyhexamides and (-)- and (+)-Hydroxyhexamides
- The Reaction of (4R, 5R)-and (4S, 5S)-4, 5-Epoxy-2(E)-Hexenoates and Secondary Amines
- The Reaction of 4,5-Epoxy-2(E)-hexenoate and Secondary Amines, Total Synthesis of (-)-Osmundalactone and (-)-Forosamine
- An Amphiphile-Lipase Aggregate Bearing 1,2-Dialkylated Mannitol Ether as a New Type of Immobilized Enzyme in Organic Solvents
- Simple Approach to Optically Active Drimane Sesquiterpenes Based on Enzymatic Resolution
- Enzymatic Hydrolysin in Organic Solvents for Kinetic Resolution of Water-Insoluble α-Acyloxy Esters with Immobilized Lipases
- Synthesis of (R)-Curcumene and (R)-Xanthorrizol Based on 1,2-Aryl Migration via Phenonium Ion
- Solvolysis of (4,5)-anti-4-Aryl-5-tosyloxy-2(E)-hexenoate Derivatives
- Enzymatic Resolution of (±)-5-Acetoxy-4-aryl-(2E)-pentenoate Derivatives
- The First Synthesis of (S)-(+)-Cacalol
- Synthesis of [[(Benzenesulfonamido)alkyl]phenyl]alkanoic Acid Derivatives Containing Pyridyl or Imidazolyl Groups and Their Thromboxane A_2 Receptor Antagonistic and Thromboxane A_2 Synthase Inhibitory Activities
- Paeoniflorin ameliorates acquisition impairment of a simple operant discrimination performance caused by unilateral nucleus basalis magnocellularis lesion in rats
- Synthesis of Methyl 1-O-(4-Hydroxymethamphetaminyl)-α-D-glucopyranouronate
- A Study for Palladium-catalyzed Chemoselective Vinylation at C-3 Position of 4-Bromo-1-tosylindole
- Substituent Effects in the Fischer Indolization of (2-Sulfonyloxyphenyl)-hydrazones (Fischer Indolization and Related Compounds . XXX)
- (1-Ethoxyvinyl)lithium in the Total Synthesis of Thymine Polyoxin C and Uracil Polyoxin C
- Neuropharmacological Actions of Pluchea indica LESS Root Extract in Socially Isolated Mice
- β-Acylation of Ethyl Pyrrole-2-carboxylate by Friedel-Crafts Acylation : Scope and Limitations (Synthetic Studies on Indoles and Related Compounds. XXXVIII)
- Chemoenzymatic Synthesis of n-Hexyl and ο-β-D-Xylopyranosyl-(1→6)-β-D-glucopyranosides
- New Strategy for Indole Synthesis from Ethyl Pyrrole-2-carboxylate (Synthetic Studies on Indoles and Related Compounds. XXXIX)
- First Synthesis of (+)-α-and (+)-γ-Polypodatetraenes
- Stereoselective Synthesis of 4'-α-Alkylcarbovir Derivatives Based on an Asymmetric Synthesis or Chemoenzymatic Procedure
- 2-Chloro-N, N-dibenzoylaniline : a Selective N-Benzoylating Reagent
- First Total Syntheses of (+)-Polyoxin B and (+)-Polyoxin D
- Synthesis of a Bridging Ligand with a Non-denatured Protein Pendant : Toward Protein Encapsulation in a Coordination Cage