60 天然型α-トコフェロールの酵素触媒による合成(ポスター発表の部)

スポンサーリンク

概要

• 論文の詳細を見る

• The α-tocopherol(vitamin E) is known as a potent and safe, lipid-soluble antioxidant. Recently, tocopherol and other antioxidants are attracting attention as scavengers of super oxide series. To our knowledge, no efficient enantioselective synthesis of d-α-tocopherol has been reported. After investigation, we have found an effective synthesis of d-α-tocopherol using the enzyme-catalyzed kinetic resolution and the conversion of unnatural enantiomer as by-product to d-α-tocopherol by racemization and repeated enzyme-catalyzed hydrolysis. We chose tocol acetate [(RS)-7] as less sterically hindered substrate for enzyme-catalyzed hydrolysis. The hydrolysis with lipaseAY(Candida rugosa) gave (R)-7 in extremely high optical yield(>99%ee),which was converted to d-α-tocopherol[(R)-1] without racemization. It is an interesting result that (RS)-7 is hydrolyzed with high enantioselectivity, in spite of the reaction site being fairly remote from the stereogenic carbon atom. The unnatural enantiomer[(S)-6] was easily racemized and then employed as a substrate of repeated enzyme-catalyzed hydrolysis. Alternatively, (RS)-10 was similarly submitted to enzyme-catalyzed hydrolysis. The (R)-10 thus obtained which was converted to d-α-tocopherol[(R)-1]. And the unnatural enantiomer[(S)-8] was also converted to d-α-tocopherol by racemization and repeated enzyme-catalyzed hydrolysis.

• 天然有機化合物討論会の論文
• 1993-09-10

著者

• 阿知波 一雄

  静岡県大薬

• 竹元 万寿美

  静岡県大薬

• 水口 栄作

  静岡県大薬

• Takemoto Masumi

  School Of Pharmaceutical Sciences(laboratory Of Medicinal Chemistry)

関連論文

• 98 蜂過敏症におけるPAFアセチルハイドラーゼ(PAF-AH)活性の検討
• Prostanoids and Related Compounds. IV. Total Synthesis of Clavulones
• Convenient Syntheses of Optically Active β-Lactams by Enzymatic Resolution
• Synthesis of Optically Active Nucleoside Analogs Containing 2,3-Dideoxyapiose in the Presence of a Catalytic Amount of Trimethylsilyl Iodide
• LIPASE-CATALYZED ENANTIOSYNTHESIS OF (R)- AND (S)-2-[BENZYL(PHENYL)AMINO]ETHYL 5-(5,5-DIMETHYL-2-OXO-1,3,2-DIOXAPHOSPHORINAN-2-YL)-1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-3-PYRIDINECARBOXYLATE (NZ 105)
• DETERMINATION OF THE ABSOLUTE CONFIGURATION OF BIOLOGICALLY ACTIVE (S)-(-)-NB 818 AND ITS STRUCTURAL CORRELATION WITH THE STEREOSELECTIVITY OF THE CHANNEL BLOCKING ACTION
• Mitogenic Activity and the Induction of Tumor Necrosis Factor by Lipopeptide Analogs of the N-Terminal Part of Lipoprotein in the Outer Membrane of Escherichia coli
• Disaccharides as Endomannosidase Inhibitors : Syntheses of α-Homomannojirimycin and β-Homomannojirimycin Linked to D-Glucose and D-Mannose
• Lipid A and Related Compounds. XXIX. Synthesis of Biologically Active N-Acylated L-Asparagine-Containing D-Glucosamine Derivatives Structurally Related to Lipid A
• 25 触媒的不斉水素化を鍵反応とする光学活性リグナン類の合成(口頭発表の部)
• Lipid A and Related Compounds. XXXVII. Determination of Favorable Binding Linkages of Lipid A Analog to Antigen Moiety for Synthetic Vaccines
• Synthesis of Cancer Peptide Antigen-Lipid A Analog Conjugates for Synthetic Vaccines
• Synthesis of Tn, Sialyl Tn and HIV-1-Derived Peptide Antigen Conjugates Having a Lipid A Analog as an Immunoadjuvant for Synthetic VAaccines
• 細菌内毒素リピドA類を免疫アジュバント部位とする癌,エイズ合成ワクチンヘの基礎研究
• SYNTHESIS OF TN AND SIALYL TN ANTIGEN-LIPID A ANALOG CONJUGATES FOR SYNTHETIC VACCINES
• Lipid A and Related Compounds. XXXIII.Synthesis and Structure-Activity Relationships of N-Acylated L-Serine or L-Threonine-Containing D-Glucosamine Derivatives as Mimics of Lipid A Disaccharide
• Lipid A and Related Compounds. XXXI.Synthesis of Biologically Active N-Acylated L-Serine-Containing D-Glucosamine 4-Phosphate Derivatives of Lipid A
• Lipid A and Related Compounds. XXX. Synthesis of Biologically Active N, N'-Diacyl Chitobiose Derivatives Structurally Related to Lipid A
• Synthesis of Ganglioside G_ and G_ Analogs Having Mimics of Ceramide Moieties and Their Binding Activities with Influenza Virus A
• Synthesis of Sulfated Cerebroside Analogs Having Mimicks of Ceramide and Their Anti-human Immunodeficiency Virus Type 1 Activities
• SYNTHESIS OF BIOLOGICALLY ACTIVE N-ACYLATED L-SERINE-CONTAINING D-GLUCOSAMINE-4-PHOSPHATE DERIVATIVES OF LIPID
• Synthesis of Peptides Mimicking Chemokine Receptor CCR5 and Their Inhibitory Effects against HIV-1 Infection
• Steric and Electronic Effects of Substrates and Rhodium Chiral Catalysts in Asymmetric Cyclopropanation
• 光学活性医薬品の触媒的不斉合成研究
• Synthesis of (β-N-Sulfonylaminoalkyl)phosphines and Their Use in Palladium-Mediated Asymmetric Synthesis
• Efficient Asymmetric Hydrogenation of β- and γ-Amino Ketone Derivatives Leading to Practical Synthesis of Fluoxetine and Eprozinol
• Efficient Asymmetric Hydrogenation of α-Amino Ketone Derivatives. A Highly Enantioselective Synthesis of Phenylephrine, Levamisole, Carnitine and Propranolol
• EFFICIENT ASYMMETRIC HYDROGENATION OF IMINES CATALYZED BY A NEUTRAL IRIDIUM(I) COMPLEX OF (4R, 5R)-MOD-DIOP
• SYNTHESIS OF IMMUNOADJUVANT CONJUGATES WITH HIV-DERIVED PEPTIDE INDUCING PEPTIDE-SPECIFIC ANTIBODY
• Preparations of Chiral Pyrrolidinebisphosphines Bearing Two Different Types of Phosphino Groups and Their Use in Efficient Catalytic Asymmetric Hydrogenation
• Prostanoids and Related Compounds. VI. Synthesis of Isoindolinone Derivatives Possessing Inhibitory Activity for Thromboxane A_2 Analog (U-46619)-Induced Vasoconstriction
• Synthesis and Mitogenic Activity of Chiral Lipopeptide WS1279 and Its Derivatives
• Synthesis of Optically Active Lipopeptide Analogs from the Outer Membrane of Escherichia coli
• SYNTHESIS OF BIOLOGICALLY ACTIVE PENTAPEPTIDE ANALOGS OF THE N-TERMALNAL PART OF LIPOPROTEIN FROM THE OUTER MEMBRANE OF ESCHERICHIA COLI
• 108(P40) 植物培養細胞を用いるポドフィロトキシン誘導体等の合成研究(ポスター発表の部)
• Synthesis of Optically Active α-Phenylpyridylmethanols with Cell Cultures of Nicotiana tabacum
• P-44 トコフェロール基本骨格の光学活性クロマンエタノールの酵素触媒合成(ポスター発表の部)
• Synthesis of Optically Active α-Phenylpyridylmethanols with Baker's Yeast
• 60 天然型α-トコフェロールの酵素触媒による合成(ポスター発表の部)
• Prostanoids and Related Compounds. V. Synthesis of 6-Aza-5-oxo-2,3,4-trinor-1,5-inter-m-phenylene Prostacyclin Derivatives
• Synthesis of Optically Active α-(p-Chlorophenyl)pyridylmethanols with Plant Cell Cultures
• Effect of Inhibitor or Immobilization on Reduction of Benzoylpyridines by Baker's Yeast
• 108(P-65) 植物培養細胞酵素によるリグナン類の骨格構築反応(ポスター発表の部)
• Asymmetric Synthesis of (R)-Nilvadipine and (S)-NB 818 via Regioselective Bromination of Chiral 1,4-Dihydropyridines as a Key Step and Enzymatic Resolution of Racemic 2-Hydroxymethyl-1,4-dihydropyridine Derivatives
• Lipase-Catalyzed Enantioselective Hydrolysis of Bis(acyloxymethyl) 1,4-Dihydro-3,5-pyridinedicarboxylates Leading to Optically Active Medicines
• Antibody-Producing Effects in Mice by Synthetic Immunoactive Lipopeptides with the Conjugated Amino Acid Sequence of gp120 in Human Immunodeficiency Virus
• Synthesis of N-Acetylglucosaminyl- and N-Acetylgalactosaminylceramides as Cerebroside Analogs and Their Anti-human Immunodeficiency Virus Type 1 Activities
• 不斉点から離れた位置に官能基を持つ化合物における酵素触媒不斉反応

もっと見る 閉じる

スポンサーリンク