Asymmetric Synthesis of α-Methylglutamic Acid and α-Methylornithine by a Chiral Isocyano Amide Reagent
スポンサーリンク
概要
- 論文の詳細を見る
An efficient approach to the asymmetric syntheses of a-methylglutamic acid and α-methylornithine is described. Two chiral reagents, (2S)-N-(2-methoxymethylpyrrolidine)-2-isocyanopropionamide 4 and (2S)-N-(2-hydroxymethylpyrrolidine)-2-isocyanopropionamide 5, were employed for the asymmetric induction. α-Methylglutamic acid 7 was synthesized by the asymmetric Michael-addition of methyl acrylate to 4 and 5 as the key step. The optical yield of 7 was 10-45% (R-form). α-Methylornithine 12 was also synthesized by the reaction of 4 with acrylonitrile as the key step. The optical yield of 12 was 31.7% (R-form).
- 社団法人 日本農芸化学会の論文
著者
-
KIRIHATA Mitsunori
Department of Agriculture, Osaka Prefectural University
-
Yamamoto Yoshihiro
Department of Genetics, Hyogo College of Medicine
-
ICHIMOTO Itsuo
Department of Agricultural Chemistry, Faculty of Agriculture, University of Osaka Prefecture
-
UEDA Hiroo
Department of Agricultural Chemistry, Faculty of Agriculture, University of Osaka Prefecture
-
Yamamoto Y
Department Of Biological Production Faculty Of Bioresource Sciences Akita Prefectural University
-
Ichimoto Itsuo
Department Of Agricultural Chemistry College Of Agriculture
-
Ueda Hiroo
Department Of Agricultural Chemistry College Of Agriculture University Of Osaka Prefecture
-
Yamamoto Yoshihiro
Department Of Biological Science Graduate School Of Science Hiroshima University
-
KIRIHATA Mitsunori
Department of Agricultual Chemistry, College of Agriculture, University of Osaka Prefecture
関連論文
- Genetic diversity and phylogeny of the endangered Okinawa Rail, Gallirallus okinawae
- Boron neutron capture therapy for newly diagnosed glioblastoma
- Evaluation of the Potential of p-Boronophenylalaninol as a Boron Carrier in Boron Neutron Capture Therapy, Referring to the Effect on Intratumor Quiescent Cells
- Cultivar Differences in the Number of Differentiated Spikelets and Percentage of Degenerated Spikelets as Determinants of the Spikelet Number per Panicle in Relation to Dry Matter Production and Nitrogen Absorption (Soil Fertility)
- Boron Neutron Capture Therapy for Newly Diagnosed Glioblastoma
- Structural Analysis of Disaccharides Synthesized by β-D-Glucosidase of Bifidobacterium breve clb and Their Assimilation by Bifidobacteria
- The Escherichia coli ldcC gene encodes another lysine decarboxylase, probably a constitutive enzyme
- Simple Synthesis of (-)-(S)- and (+)-(R)-2,2-Dimethyl-1-aminocyclopropane-1-carboxylic Acid (2,2-Dimethyl-ACC)(Organic Chemistry)
- Influences of Nitrogen Sources on Usnic Acid Production in a Cultured Mycobiont of the Lichen Usnea hirta (L.) Wigg.(Microbiology & Fermentation Technology)
- Difference of Cell-viability and Spore Discharge Capability between Two Lichen Species,Letharia columbiana (Nutt.) Thoms. and L. vulpina (L.) Hue.
- Distribution of optical isomers of usnic and isousnic acids analyzed by high performance liquid chromatography
- Cytochromes in the Cultured Mycobiont of a Lichen, Cladonia vulcani Sav. : PROTEINS, ENZYMES AND METABOLISM : MEMBRANES AND BIOENERGETICS
- Anthocyanin Production in Cultured Euphorbia millii Cells Using FiIm Culture Vessels
- Improvement of Protoplast Isolation from Lichen Mycobionts(Biological Chemistry)
- Anthocyanin Production in Suspension Cultures of High-producing Cells of Euphorbia millii
- Asymmetric Synthesis of α-Methylglutamic Acid and α-Methylornithine by a Chiral Isocyano Amide Reagent
- Asymmetric Synthesis of α-Alkylamino Acid by Chiral Isocyano Amide Reagent
- Lysis of Yeast Cells Showing Low Susceptibility to Zymolyase
- Genotypic Differences in Dry Matter Accumulation, Nitrogen Use Efficiency and Harvest Index in Recombinant Inbred Lines of Rice under Hydroponic Culture
- Genotypic differences in grain yield, and nitrogen absorption and utilization in recombinant inbred lines of rice under hydroponic culture(Soil Chemistry and Mineralogy)
- 中国産多収性インド型品種揚稲4号のシンク大小に及ぼす緩効肥の影響(日本作物学会四国支部第42回講演会講演要旨)
- Effects of the Tillering Nodes on the Main Stem of a Chinese Large-Panicle-Type Rice Cultivar, Yangdao 4, on the Growth and Yield-Related Characteristics in Relation to Cropping Season
- Responses of Yielding Ability, Sink Size and Percentage of Filled Grains to the Cultivation Practices in a Chinese Large-Panicle-Type Rice Cultivar, Yangdao 4
- Asymmetric Reduction of Ethyl 2-methyl 3-oxobutanoate by Fungi
- Asymmetric Reduction of Ethyl 2-methyl 3-oxobutanoate by Chlorella
- Nutrient Availability and Response of Sago Palm (Metroxylon sagu Rottb.) to Controlled Release N Fertilizer on Coastal Lowland Peat in the Tropics
- Two-dimensional electrophoretic analysis of disease-associated proteins in human cerebrospinal fluid from patients with rheumatoid arthritis
- Change in the Cell Cycle during Development of Chick Telencephalon(短報)
- Fluoroscopically Assisted Hybrid Thrombectomy : An Improved Method for Treating Acute Limb Ischemia(Peripheral Circulation/Vascular Disease 5 (H), The 69th Annual Scientific Meeting of the Japanese Circulation Society)
- Importance of Controlling Drug-resistant Pseudomonas aeruginosa Infection: Experience from Lung Transplantation in a Cystic Fibrosis Case
- Possible Involvement of Optimally Phosphorylated L-Plastin in Activation of Superoxide-Generating NADPH Oxidase
- Intracavernous Cavernous Hemangioma: Dynamic CT Findings and Effectiveness of Irradiation : Case Report
- Enhancement of the Effectiveness of Indigenous Arbuscular Mycorrhizal Fungi by Inorganic Soil Amendments
- Overcrowding Factors of Mosqutio Larvae X. Structure-Bioactivity Relationship and Bacterial Activation of the Alkyl-branched
- Studies on the Mechanism of Aluminum Tolerance in Pea (Pisum sativum L.) Using Aluminum-Tolerant Cultivar 'Alaska' and Aluminum-Sensitive Cultivar 'Hyogo'(Plant Nutrition)
- CARBOXYL-TERMINAL EXTENSION OF PRECURSOR D1 PROTEIN IS EXCISED WITH TWO STEPS BY CTPA IN SYNECHOCYSTIS 6803
- TOLERANT MECHANISMS TO THE PEROXIDATION OF LIPIDS IN AN ALUMINUM-TOLERANT TOBACCO CELL LINE-GLUTATHIONE PEROXIDASE (GPx) AND GLUTATHIONE-S-TRANSFERASE (GST)
- PROTECTIVE EFFECTS OF ANTIOXIDANTS ON ALUMINUM-INDUCED MITOCHONDRIAL DYSFUNCTION IN CULTURED TOBACCO CELLS
- ALUMINUM INDUCES THE DYSFUNCTION OF MITOCHONDRIA IN CULTURED TOBACCO CELLS
- Morphological and Anatomical Observations of Adventitious and Lateral Roots of Sago Palms
- A New Cytotoxic Compound from a Water Extract of Corn
- Levels of spinorphin in cerebrospinal fluid derived from patients with pain increase with decreasing dipeptidyl peptidase III
- Selenite Assimilation into Formate Dehydrogenase H Depends on Thioredoxin Reductase in Escherichia coli
- Effects of Sugar Acids on the Functions of Ribulose Bisphosphate Carboxylase/Oxygenase : Differentiation of Two Different Ligand-binding Modes of the Catalytic Sites
- Synthesis of O-[(o-Carboran-1-yl)methyl]-3-hydroxytyrosine, a Novel p-Boronophenyl-alanine Analogue for Boron Neutron Capture Therapy
- Synthesis of p-Boronophenylserine, a New Boron-containing Amino Acid for Boron Neutron Capture Therapy
- A Simple and Improved Synthesis of p-Boronophenylalanine, a Boron Carrier for the Boron-Neutron Capture Therapy
- Heterosis in Numbers of Differentiated, Degenerated, and Surviving Spikelets and Their Relations to the Dry Matter Production in F_1 Hybrids of Rice
- Importance of Psycho-social Aspect of Diabetics for Pancreas Transplantation in Japan
- Enantioselective Synthesis of Both Enantiomers of Dimethyl cis-(4-Acetoxycyclopent-2-enyl)malonate, Key Intermediates for Epijasmonate(Organic Chemistry)
- Alkylation of Diethyl 3-Oxoglutarate with α,ω-Dibromoalkanes(Organic Chemistry)
- Quinoxalines Derived from D-Glucose and Maltose with o-Phenylene-diamine under Refluxed Conditions in Alkaline Media
- Differences in bleeding rate during panicle formation stage and its influence on the sink size of different grain size cultivars
- Relation between Bleeding Rate during Panicle Formation Stage and Sink Size in Rice Plant(Soil Fertility)
- 11-11 Characteristics of Spikelet Differentiation and Degeneration Among Rice Cultivars Belongs to Different Eco-species of Rice
- Spatial Localization of Mono- and Diphosphorylated Myosin II Regulatory Light Chain at the Leading Edge of Motile HeLa Cells
- Simple Synthesis of Both Enantiomers of the C7-C12 Segment of Epothilones
- Determination of the complete nucleotide sequence and haplotypes in the D-loop region of the mitochondrial genome in the Oriental white stork, Ciconia boyciana
- Amino Acid and Peptide Derivatives of Kojic Acid and Their Antifungal Properties(Pesticide Chemistry)
- The Opioid Activity and Receptor Selectivity of Fluorinated Leu^5 Enkephalin Analogues in Vitro and in Vivo
- Stereoselective Synthesis of Unnatural Stereoisomers of LL-P880β and LL-P880γ, Pestalotin Analogues from Penicillium sp.
- Total Synthesis of (6S,1'S,2'R)-6-(1',2'-Dihydroxypentyl)-4-methoxy-5,6-dihydropyrane-2-one (LL-P880β) and Its C_6-Epimer, a Fungal Metabolite from Penicillium sp.(Organic Chemistry)
- An Effective Synthesis of (±)-(E)-2-Amino-5-phosphono-3-pentenoic Acid by Palladium(II)-assisted Migration of the Double Bond(Organic Chemistry)
- Stereoselective Synthesis of Marine Antibiotic (-)-Malyngolide and Its Stereoisomers(Organic Chemistry)
- Isolation of Conduritol A from Gymnema sylvestre and Its Effects against Intestinal Glucose Absorption in Rats
- Synthesis of the Spirosuccinimide Moiety of Asperparaline A
- Synthesis and Structural Confirmation of (2S, 3R, 4R, 6E)-2-Acetylamino-3-hydroxy-4-methyl-6-octenoic Acid, a New Amino Acid Produced by Neocosmospora vasinfecta
- Effect of Conduritol A, a Polyol from Gymnema sylvestre, on the Development of Diabetic Cataracts in Streptozotocin-treated Rats and on Aldose Reductase
- Occurrence of Diglycerol Tetradodecanoate Tetradecanedioate in Scale Insect, Phenacoccus pergandei COCKERELL (Hemiptera : Pseudococcidae)
- LOCALIZATION OF PHOSPHORYLATED REGULATORY LIGHT CHAIN OF MYOSIN II DURING CYTOKINESIS(Cell Biology and Morphology,Abstracts of papers presented at the 75^ Annual Meeting of the Zoological Society of Japan)
- Levels of Superoxide Dismutases, Glutathione, and Poly (ADP-ribose) Polymerase in Radioresistant Human KB Carcinoma Cell Line
- Asymmetric Synthesis of D-(E)-2-Amino-5-phosphono-3-pentenoic Acid (APPA) by Using a Chiral Auxiliary
- Synthesis and Biological Activity of LL-P880γ and Its Analogues
- Determination of the complete genomic DNA sequence of Thermoplasma volcanium GSS1
- An Efficient Synthesis of (±)-α-Kainic Acid Using a 3-Hydroxyallylglycine Derivative as a Common Building Block(Organic Chemistry)
- Studies on Kojic Acid Derivatives : Part 4. Some Reactions of Kojic Acid
- Studies on Kojic Acid Derivatives : Part 3. Coupling Reaction of Kojic Acid with Diazonium Salts
- Measurement of Blood Flow Velocity in Feeder Vessels of Chorodial Neovascularization by a Scanning Laser Ophthalmoscope and Image Analysis System
- Genetic diversity and phylogeny of the endangered Okinawa Rail, Gallirallus okinawae
- Enzymatic Deamination of ( ± )-2-Methyl- and (S)-2,2-Dimethyl-1-aminocyclopropane-1-carboxylic Acid
- Charge Distribution of Pions produced in High Energy Nuclear Collisions
- Studies on Kojic Acid Derivatives : The Acylation of Kojic Acid
- Characteristics and disease severity of healthcare-associated pneumonia among patients in a hospital in Kitakyushu, Japan
- (S)-3-Acethyl-1,2-Diacyl-sn-Glycerols from the Lipids of Drosicha corpulenta KUWANA (Homoptera : Margarodidae)
- An Autopsy Case of Erysipelothrix Rhusiopathiae Endocarditis
- Immediate Single Lobar Retransplantation for Primary Graft Dysfunction After Living-Donor Lobar Lung Transplantation : Report of a Case
- The efficacy and safety of high-dose arbekacin sulfate therapy (once-daily treatment) in patients with MRSA infection
- Severe Legionnaires' Disease Successfully Treated Using a Combination of Fluoroquinolone, Erythromycin, Corticosteroid, and Sivelestat
- A Convenient Synthesis of Four Stereoisomers of 6-Acetoxy-5-hexadecanolide, the Major Component of the Mosquito Oviposition Attractant Pheromone
- An Efficient Synthetic Method for (±)-Malyngolide and Its Optical Resolution
- Nationwide, multicenter survey on the efficacy and safety of piperacillin for adult community-acquired pneumonia in Japan
- A Clinical Comparative Study of Piperacillin and Sulbactam/Ampicillin in Patients with Community-Acquired Bacterial Pneumonia
- Spontaneous Pyogenic Spondylitis Caused by Klebsiella pneumoniae
- A Case of Refractory Chronic Respiratory Tract Infection due to Pseudomonas aeruginosa Successfully Controlled by Combination of Clarithromycin and Azithromycin
- A Case Series of Chronic Necrotizing Pulmonary Aspergillosis and a New Proposal
- Biosynthesis of Grayanotoxins in Leucothoe grayana Max. Incorporation of Mevalonic Acid and (-)-Kaurene into Grayanotoxin-III
- Synthesis of Pyrazinedicarboximides from Diaminomaleonitrile
- Prospective randomized comparison study of piperacillin/tazobactam and meropenem for healthcare-associated pneumonia in Japan
- Comparison of effective impact among tonsillectomy alone, tonsillectomy combined with oral steroid and with steroid pulse therapy on long-term outcome of immunoglobulin A nephropathy