Studies on the Metabolism of Unsaturated Fatty Acids. I. Synthesis and Identification of 6-Hydroxydodec-3-cis-enoic Acid, the Final Metabolite of Ricinoleic Acid by Escherichia coli K-12
スポンサーリンク
概要
- 論文の詳細を見る
6-Hydroxydodec-cis-3-enoic acid was synthesized to identify a metabolite of ricinoleic acid by Escherichia coli and to use it as substrate in the investigation on unsaturated fatty acid metabolism. In a total synthesis of the 6-hydroxy acid, the key step involved the reaction of the trialkynylborane with ethyl diazoacetate. Dec-1-yn-4-ol was lithiated after protection of the hydroxyl group with dihydropyran, and was transformed into the trialkynylborane by treating with boron trifluoride etherate. The subsequent reaction with ethyl diazoacetate afforded the 6-hydroxy-3-ynoate, which was hydrogenated over Lindlar catalyst to yield 6-hydroxydodec-3-cis-enoic acid. The results obtained by gas chromatography-mass spectrometry (GC-MS) showed that the final metabolite of ricinoleic acid by E. coli was identical with the synthetic 6-hydroxy acid.
- 公益社団法人日本薬学会の論文
- 1978-08-25
著者
-
水柿 道直
Pharmaceutical Institute Tohoku University
-
坂本 尚夫
Pharmaceutical Institute, Tohoku University
-
山中 宏
Pharmaceutical Institute, Tohoku University
-
福山 はる
Pharmaceutical Institute, Tohoku University
-
福山 はる
Pharmaceutical Institute Tohoku University
-
坂本 尚夫
Pharmaceutical Institute Tohoku University
関連論文
- Condensed Heteroaromatic Ring Systems. XVI. : Synthesis of Pyrrolo[2,3-d]pyrimidine Derivatives
- Studies on Pyrimidine Derivatives. XLI. : Palladium-Catalyzed Cross-Coupling Reaction of Halopyrimidines with Aryl- and Vinyltributylstannanes
- Condensed Heteroaromatic Ring Systems. VII : Synthesis of Thienopyridines, Thienopyrimidines, and Furopyridines from o-Substituted N-Heteroarycetylenes
- Separation and Some Characterizations of NADPH-Enoyl CoA Reductase (s) from Candida albicans
- 大麻成分の理化学的試験
- Studies on Pyrimidine Derivatives. XXX. The Palladium-Catalyzed Cross-Coupling Reaction of Iodopyrimidines with Terminal Olefinic Compounds
- Studies on Quinoline and Isoquinoline Derivatives. II. Coupling Reaction of Haloquinolines and Haloisoquinolines with Monosubstituted Acetylenes in the Presence of Palladium Complex
- Studies on Pyrimidine Derivatives. X. Coupling Reaction of 5-Halopyrimidines with Olefinic Compounds in the Presence of Palladium Acetate and Triphenylphosphine
- Studies on Pyrimidine Derivatives. IX. Coupling Reaction of Monosubstituted Acetylenes with Iodopyrimidines
- Studies on Pyrimidine Derivatives. VII. Nickel-Phosphine Complex-Catalyzed Grignard Coupling of Chloropyrimidines
- Antivertigo Agents. IV. Synthesis and Antivertigo Activity of 6-[ω-(4-Aryl-1-piperazinyl) alkyl]-5,6,7,8-tetrahydro-1,6-naphthyridines
- Keteneおよびその誘導体の研究(第40報) : N-Ethylideneisopropylamine, N-Methylenecyclohexylamine, およびN-Methylene-tert-butylamineとDiketeneとの反応
- Keteneおよびその誘導体の研究(第16報) : Schiff BaseとDiketeneとの反応
- Studies on Pyrimidine Derivatives. XXXIII. Synthesis of Alkyl Pyrimidinyl Ketones by Means of Nitrosation of Alkylpyrimidines
- Studies on Pyrimidine Derivatives. XXVII. Synthesis of 2- and 4-Pyrimidinyl Ketones by Means of the Hydration of Alkynylpyrimidines
- Studies on Pyrimidine Derivatives. XXVI. Synthesis of Derivatives containing a 1,3-Dicarbonyl Side Chain
- Studies on Ketene and Its Derivatives. LXXV. Reaction of Diketene with N-Benzylacetimidate and Lactim Ethers to give 1,6-Naphthyridine Derivatives
- Studies on Quinoline and Isoquinoline Derivatives. VI. Addition Reaction of Diketene with Isoquinolines in the Presence of Carboxylic Acids
- Studies on Pyrimidine Derivatives. XXV. Reaction of Pyrimidinyl Aldehydes and Ketones with Witting Reagents
- Studies on Pyrimidine Derivatives. XX. Synthetic Utility of Hydroxymethylpyrimidines and Related Compounds
- Isoxazole Derivatives as Centrally Acting Muscle Relaxants. II. : Synthesis and Structure-Activity Relationship of 3-Amino-N-(3-phenyl-5-isoxazolyl)propanamides
- Isoxazole Derivatives as Centrally Acting Muscle Relaxants. I. : Synthesis and Activity of 5-(3-Aminopropyl)amino-3-phenylisoxazole Derivatives
- Antivertigo Agents. V. Quantitative Structure-Activity Relationships of 6-[2-(4-Aryl-1-piperazinyl) ethyl]-5,6,7,8-tetrahydro-1,6-naphthyridines
- Antivertigo Agents. III. Synthesis of 5,6,7,8-Tetrahydro-1,6-naphthyridine Methyl Homologs
- Antivertigo Agents. II. Structure-Activity Relationships of 6-Substituted 5,6,7,8-Tetrahydro-1,6-naphthyridines
- Antivertigo Agents. I. Structure-Activity Relationships of 2-(2-Aminoethyl) pyridines
- Studies on Pyrimidine Derivatives. XIX. Synthesis of Isoxazolo [5,4-d] pyrimidines
- Molecular Orbital Study of the Nitrosation of Active Methyl and Methylene Groups of Pyridine and Pyrimidine Derivatives
- Molecular Orbital Study of the Reactivity of Active Alkyl Groups of Pyridine and Pyrimidine Derivatives
- Studies on Ketene and Its Derivatives. XLVII. Reaction of 2-Aminopyridine with Diketene
- Studies on Ketene and Its Derivatives. XLVI. Mass Spectrometric Studies of 3-Acetyl-4-hydroxy-6-methyl-1-pyridyl-2-pyridones and N-Pyridyl-2,6-dimethyl-4-pyrone-3-carboxamides
- Studies on the Metabolism of Unsaturated Fatty Acids. VII. Separation and General Properties of Reduced Nicotinamide Adenine Dinucleotide Phosphate-dependent trans-2-Enoyl-Coenzyme A Reductase from Escherichia coli K-12
- Studies on the Metabolism of Unsaturated Fatty Acids. VI. Stereochemical Studies of the Reaction catalyzed by cis-2-Enoyl-Coenzyme A Reductase of Escherichia coli
- Studies on the Metabolism of Unsaturated Fatty Acids. V. Isomerization of Thiol Esters of cis-2-Alkenoic Acids during Their Preparation and Alkaline Hydrolysis
- Studies on Pyrimidine Derivatives. XXIV. Synthesis of 3-Substituted 1,2,4-Triazines by Nucleophilic Substitution
- Studies on the Metabolism of Unsaturated Fatty Acids. IV. N-Ethylmaleimide Reducing Activity in Escherichia coli K-12
- Studies on the Metabolism of Unsaturated Fatty Acids. III. Structural Determination of cis- and trans-Isomers of 3- or 2-Alkenoic Acids by Nuclear Magnetic Resonance Spectroscopy using a Chemical Shift Reagent
- Studies on Pyrimidine Derivatives. XIV. On the Structural Determination of Pyrimidine N-Oxides
- Studies on the Metabolism of Unsaturated Fatty Acids. II. Separation and General Properties of Reduced Nicotinamide Adenine Dinucleotide Phosphate dependent cis-2-Enoyl-Coenzyme A Reductase from Escherichia coli K-12
- Studies on Pyrimidine Derivatives. XII. Reaction of 4,6-Disubstituted Pyrimidine N-Oxides with Dimethyl Acetylenedicarboxylate
- Studies on the Metabolism of Unsaturated Fatty Acids. I. Synthesis and Identification of 6-Hydroxydodec-3-cis-enoic Acid, the Final Metabolite of Ricinoleic Acid by Escherichia coli K-12
- Palladium-Catalyzed Condensatino of Aryl Halides with Phenylsulfonylsulfonylacetonitrile and Diethyl Cyanomethyl phosphonate
- Cross-Coupling of N-Heteroaryl Halides with Active Methylene Compounds in the Presence of Tetrakis(triphenylphosphine)palladium
- MNDO (Modified Neglect of Diatomic Overlap) Study of the Nucleophilic Substitution Reactions of Chloropyrimidines
- Studies on Pyrimidine Derivatives. XXI. Nucleophilic Substitution of 4-Chloropyrimidines and Related Compounds with Carbanions
- Studies on Pyrimidine Derivatives. XVIII. Reaction of Active Methyl Groups on Pyrimidine N-Oxides
- Studies on Quinoline and Isoquinoline Derivatives. III. Reaction of Quinoline 1-Oxide with 2-Substituted Ethyl Acetimidates
- Studies on Pyrimidine Derivatives. VIII. Ring-Cleavage Reaction of 4,6-Dimethylpyrimidine 1-Oxide
- Studies on Ketene and Its Derivatives. LX. Reaction of Diketene with Quinoline 1-Oxide (Supplement)
- Keteneおよびその誘導体の研究(第45報) : 2-Alkyl-2-imidazolineとDiketeneとの反応
- Studies on as-Triazine Derivatives. XVI. Reaction of 1,2,4-Triazinecarbonitriles with Carbanions
- Studies on as-Triazine Derivatives. XII. : Synthesis of Alkenyl-1,2,4-triazine Derivatives
- Studies on as-Triazine Derivatives. IX. Synthesis of 5-Substituted 1, 2, 4-Triazine Derivatives through an Addition Reaction and Subsequent Oxidation(Organic,Chemical)
- Studies on Quinoline and Isoquinoline Derivatives. VIII. Hydration and Hydrogenation of Ethynyl Substituents attached to the Pyridine Moiety of Quinoline and Isoquinoline Rings
- Hydration and Hydrogenation of Acetylenic Side-Chains at the 4- or 5-Position of Isoxazoles
- Studies on Pyrimidine Derivatives. XXIII. Synthesis of Acylmethylpyrimidines and Related Compounds via Imidoyl-substituted Oxosulfonium Ylides
- Studies on Quinoline and Isoquinoline Derivatives. IV. Reaction of Quinoline and Isoquinoline N-Oxides with 3-Amino-crotononitrile and Related Compounds
- Studies on Quinoline and Isoquinoline Derivatives. I. Condensation of Quinoline and Isoquinoline N-Oxides with Isoxazoles
- Synthesis of Ethoxyethynylarenes by the Palladium-Catalyzed Reaction of Aryl Iodides with Ethoxy(trialkylstannyl)acetylenes
- 1,3-Dipolar Cycloaddition Reaction of Substituted Trimethylstannylacetylenes with Nitrile Oxides
- Condensed Heteroaromatic Ring Systems. XXI.Synthesis of Pyrrolo[2,3-d]pyrimidines and pyrrolo[3,2-d]pyrimidines
- Condensed Heteroaromatic Ring Systems. XX. Palladium-Catalyzed Carbonylative Coupling of Iodobenzenes with (Z)-1-Ethoxy-2-(tributylstannyl)ethene
- Palladium-Catalyzed Coupling Reaction of 3-Iodoindoles and 3-Iodobenzo[b]thiophene with Terminal Acetylenes
- Site-Selectivity in the Reaction of 3-Substituted Pyridine 1-Oxides with Phosphoryl Chloride
- Condensed Heteroaromatic Ring Systems. XV. : Synthesis of Pyranopyridinones from Halopyridinecarbonitriles
- Condensed Heteroaromatic Ring Systems. XIII. : One-Step Synthesis of 2-Substituted 1-Methylsulfonylindoles from N-(2-Halophenyl)methanesulfonamides
- Studies on Pyrimidine Derivatives. XL. : Ring Transformation of 4-Alkoxypyrimidine 1-Oxides by Reaction with Diketene
- Condensed Heteroaromatic Ring Systems. XII. Synthesis of Indole Derivatives from Ethyl 2-Bromocarbanilates(Organic,Chemical)
- Studies on Ketene and its Derivatives. VI. Reaction of Diketene with Aminopyridines and their N-Oxides
- Studies on Ketene and Its Derivatives. XXVIII. Reaction of β-Aminocrotonamide with Ketene and Diketene
- Reductive Amination of Ethynylpyridines with Sodium Cyanoborohydride
- Condensed Heteroaromatic Ring Systems. IX. : Total Synthesis of Aaptamine
- Condensed Heteroaromatic Ring Systems. V. : Formal Synthesis of Matrine and Related Compounds Using Palladium-Catalyzed Carbon-Carbon Bond Formations as Key Reactions
- Palladium-Catalyzed Reactions of Terminal Acetylenes and Olefins with Halo-1,3-azoles(Organic,Chemical)
- Studies on Pyrimidine Derivatives. XV. Homolytic Acylation and Amidation of Simply Substituted Pyrimidines
- Studies on the Synthesis of Indole Related Compounds. II. Diels-Alder Reaction of Phenacylidene Indolinone
- Studies on Quinoline and Isoquinoline Derivatives. IX. Synthesis of Pyrrolo [1,2-b] isoquinolines from 3-Bromoisoquinoline Derivatives
- Cross-coupling Reactions of Haloisoxazoles with Olefins and Acetylenes
- Studies on Pyrimidine Derivatives. VI. On the Reactivity of the 2-Methyl Group of 1,2,4-Trimethyl-6-oxo-1,6-dihydropyrimidine
- Studies on Pyrimidine Derivatives. II. Reaction of Some Dimethyl and Trimethyl-heteroaromatics with Ethyl Nitrite
- N-Oxidation of 4-Chloropyrimidine Derivatives
- Studies on Ketene and Its Derivatives. XXXII. Reactions of α, β-Unsaturated Acid Anhydride with β-Aminocrotonamide and Related Compounds
- Site-Selectivity in the Cyanation of 3-Substituted Pyridine 1-Oxides with Trimethylsilanecarbonitrile
- Studies on Ketene and Its Derivatives. XII. The Structure of the Self-Condensation Product of Acetoacetamide.
- Studies on Pyrimidine Derivatives. XXXIV. Substituent Effect on the Reaction of 4-Substituted 2,6-Dimethylpyrimidine 1-Oxides with Acetic Anhydride
- Studies on Pyrimidine Derivatives. XXXII. Reaction of 4-Substituted 2,6-Dimethylpyrimidine 1-Oxides with Phosphoryl Chloride
- Keteneおよびその誘導体の研究(第24報) : DiketeneとKetimineとの反応
- Studies on Pyrimidine Derivatives. XXXVI. Reaction of 6-Substituted 2,4-Dimethylpyrimidines with Benzaldehyde in the Presence of Zinc Chloride
- Condensed Heteroaromatic Ring Systems. III. Synthesis of Naphthyridine Derivatives by Cyclization of Ethynylpyridinecarboxamides
- Condensed Heteroaromatic Ring Systems. VIII. : Synthesis of 3-Substituted Isocoumarins from o-Halobenzoic Acid Derivatives
- Condensed Heteroaromatic Ring Systems. VI. : Synthesis of Indoles and Pyroolopyridines from o-Nitroarylacetylenes
- Condensed Heteroaromatic Ring Systems. IV. Synthesis of Naphthyridine Derivatives by Cyclization of Aminopyridineacrylic Esters
- Studies on Pyrimidine Derivatives. XXXVIII. Cross-Coupling Reaction of N-Heteroaryl Iodides with Ethoxycarbonylmethylzinc Bromide in the Presence of Palladium Catalyst
- Studies on Quinoline and Isoquinoline Derivatives. VII. Addition Reactions of Acetic Anhydride and Active Methylene Compounds to the Carbon-Nitrogen Double Bond of the Isoquinoline Ring
- Studies on Quinoline and Isoquinoline Derivatives. V. Reaction of Isoquinoline 2-Oxide with Diketene
- Studies on Pyrimidine Derivatives. XIII. Reaction of 4-Alkoxypyrimidine 1-Oxides with Phenyl Isocyanate and Phenyl Isothiocyanate
- Studies on Pyrimidine Derivatives. I. Reaction of Pyrimidine N-Oxides with Enamines
- Studies on Pyrimidine Derivatives. XXII. Site-selective Oxidation of Dimethylpyrimidines with Selenium Dioxide to Pyrimidine-minoaldehydes
- Studies on Pyrimidine Derivatives. XVI. Site Selectivity in the Homolytic Substitution of Simple Pyrimidines
- Studies on Pyrimidine Derivatives. V. Reaction of 2,4-Dimethylazines with Ethyl Benzoate under Basic Conditions