53 桿菌tRNA構成成分,7-Methyladenosineの合成と加水分解(口頭発表の部)
スポンサーリンク
概要
- 論文の詳細を見る
7-Methyladenosine (4a), whose existance in tRNAs of Bacillus stearothermophilus and B. subtilis has been suggested, was synthesized in the form of the crystalline perchlorate salt from N^6-methoxyadenosine (5). Methylation of 5 with MeI in AcNMe_2 produced N^6-methoxy-7-methyladenosine, which was isolated in the form of the sulfate [7a (X = 1/2SO_4)], together with the N^6-methoxy-N^6-methyladenosine (9a) as a by-product. Demethoxylation of 7a (X = 1/2SO_4) by catalytic hydrogenolysis using hydrogen and Raney Ni catalyst produced, after replacement of the anion with perchlorate ion, 7-methyladenosine perchlorate [4a (X = ClO_4)]. 7-Ethyladenosine perchlorate [4b (X = ClO_4)] was also synthesized from N^6-benzyloxyadenosine (6) through a parallel route via N^6-benzyloxy-7-ethyladenosine sulfate [8b (X = 1/2SO_4)]. On treatment with H_2O at 98-100℃ for 40 min, 4a (X = ClO_4) and 4b (X = ClO_4) furnished 7-methyladenine (11a) and 7-ethyladenine (11b), respectively. Similar hydrolysis of 7a (X = 1/2SO_4) gave N^6-methoxy-7-methyladenine (12). In 0.1 N aqueous HCl at 25℃, 4a (X = ClO_4) and 4b (X = ClO_4) were found to undergo glycosidic hydrolysis at rates of 2.22 x 10^<-3> min^<-1> and 1.69 x 10^<-3> min^<-1>, respectively. Comparison of these rate constants with those of the other three N^x-methyladenosines (1-3) has revealed that the ease with which depurinylation occurs decreases in going through the series 3-(2)>7-(4a)≫N^6-(3)≧1-methyladenosine (1). On treatment with 1 N aqueous NaOH at 60℃ for 3h, 4a (X = ClO_4) was hydrolyzed to give 11a.
- 天然有機化合物討論会の論文
- 1990-09-25
著者
-
斎藤 徹
Faculty Of Pharmaceutical Sciences Kanazawa University
-
藤井 澄三
Shinshu Univ. Nagano Jpn
-
藤井 澄三
金沢大・薬
-
斎藤 徹
金沢大・薬
関連論文
- 天然含窒素複素環の化学(その2)プリン塩基・ヌクレオシドの合成と反応
- 天然含窒素複素環の化学(その1)数種の植物に出現するBenzo[α]quinolizidine環系及びIndolo[2,3-α]quinolizidine環系アルカロイドの合成と構造決定
- 含窒素複素環の化学 : 私の40年
- 日本薬学会教育賞受賞笹本光雄氏の業績
- 日本薬学会学術賞紹介 日野亨氏の業績
- Purines. LXX. An Extension of the "Phenacylamine Route" to the Syntheses of the 7-N-Oxides of 6-Mercaptopurine and 6-Methylthiopurine, and Antileukemic Activity of Some Purine N-Oxides
- Purines. LXIX. Direct N(1)-Oxidation of 7-Benzyladenine and Stepwise Syntheses of Its N(1)- and N(3)-Oxides
- Purines. LXVIII. Trifluoroperoxyacetic Acid Oxidation of N^6-Benzyladenine : Formation of the N(3)-Oxide and N(7)-Oxide, and Their Cytokinin Activities
- Purines. LXVII. An Alternative Synthesis of Adenine 7-Oxide : N-Oxidation of the Adenine Ring Utilizing Blocking/Deblocking at the 1-Position
- Purines. LXVI. Adenine 7-Oxide : Its Synthesis, Chemical Properties, and X-ray Molecular Structure
- Purines. LII. Synthesis and Biological Evaluation of 8-Methylguanine 7-Oxide and Its 9-Arylmethyl Derivatives
- Purines. LI. Synthesis and Biological Activity of Hypoxanthine 7-N-Oxide and Related Compounds
- Purines. L. Synthesis and Antileukemic Activity of the Antibiotic Guanine 7-Oxide and Its 9-Substituted Derivatives
- 2-(3-Pyridyl)thiazolidine-4-carboxamide Derivatives. II. Structure-Activity Relationships and Active Configuration of 2-(3-Pyridyl)thiazolidine-4-carboxamides as Platelet-Activating Factor Receptor Antagonists
- 2-(3-Pyridyl)thiazolidine-4-carboxamides. 1. Novel Orally Active Antagonists of Platelet-Activating Factor (PAF)
- Purines. LX. Dimroth Rearrangement and Concomitant Hydrolytic Deamination of 7-Alkyl-1-methyladenines
- Involvement of a Cytochrome P4502D Subfamily in Human Liver Microsomal Bunitrolol 4-Hydroxylation
- Variable glyceryl dinitrate formation as a function of glutathione S-transferase.
- Variable Glyceryl Dinitrate Formation as a Function of Glutathione S-Transferase
- Synthesis and Biological Activity of the Metabolites of N-[2-(1-Azabicyclo[3.3.0]octan-5-yl)ethyl]-2-nitroaniline Fumarate (SK-946)
- Synthesis of (1-Azabicyclo[3.3.0]octanyl)methyl-Substituted Aromatic Heterocycles and Their Muscarinic Activity
- Synthesis and Thromboxane A_2 Antagonistic Activity of [[1-Aryl(or Benzyl)-1-(benzenesulfonamide)methyl]phenyl]alkanoic Acid Derivatives
- Quinolizidines. XXVI. : A Synthesis of (±)-Deplancheine
- Laxative and Anti-diarrheal Activity of Polycarbophil in Mice and Rats
- An Improved Synthesis of Butyl 4-[(4-Amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidineacetate (AU-224)
- Synthesis and Gastrointestinal Prokinetic Activity of Novel Benzamide Derivatives with Amphoteric Side Chains
- Calcium Polycarbophil, a Water Absorbing Polymer, Increases Bowel Movement and Prevents Sennoside-Induced Diarrhea in Dogs
- Purines. XLI. : An Alternative Synthesis and the Chemical Behavior of 7,9-Dialkyladeninium Salts
- Purines. XXXVIII. A General Synthesis of 7,9-Dialkyladeninium Salts from 9-Alkyladenines by Regioselective Alkylation : Utilization of an N^6-Alkoxy Group as a Control Synthon
- Purines. XXX. : Ring Fission of 3,7-Dialkyladenines by Alkaline Hydrolysis
- Purines. XXVIII. Preparation of Some 3,7-Dialkyladenines from 3-Alkyladenines by Alkylation : A Subordinate Formation of 3,9-Dialkyladenines
- Purines. XXI. Synthesis of Adenine 1-Oxides Carrying an Allylic Side Chain at the 9-Position
- Decalcification of Calcium Polycarbophil in Rats
- Structure-Activity Relationship(SAR)Studies on Oxazolidinone Antibacterial Agents.1. Conversion of 5-Substituent on Oxazolidinone
- Cytotoxicity of Organochlorine Pesticides and Lipid Peroxidation in Isolated Rat Hepatocytes
- Cytotoxicity of Organochlorine Pesticides and Lipid Peroxidation in Rat Hepatocytes (Proceedings of the 22nd Symposium on Toxicology and Environmental Health)
- Cytotoxicity of Paraquat and Phospholipid Peroxidation in Rat Hepatocytes (Proceedings of the 21st Symposium on Toxicology and Environmental Health)
- Cytotoxicity of Halogenated Hydrocarbons and Cellular Phospholipid Peroxidation in Isolated Rat Hepatocytes (Proceedings of the 20th Symposium on Toxicology and Environmental Health)
- Characterization of the Neurochemical Effects of N-[2-(1-azabicyclo[3,3,0]octan-5-yl)ethyl]2-nitroaniline fumarate (SK-946) as a Cognition Activator
- P-3 海綿由来アデニン環含有ジテルペノイドの合成研究 : (±)-Agelasimine-Aおよび(±)-Agelasimine-Bの合成(ポスター発表の部)
- Purines. LXV. Preparatory study for the syntheses of the marine sponge purines agelasimines-A and -B: Synthesis and acetylation of their N(7)-benzyl analogues
- Purines. LXIV. Syntheses of 9-Methyl-2-azaadenine 1-Oxide, Its O-Methyl Derivative, and 1-Substituted 5-Azidoimidazole-4-carboxamides
- Purines. LXIII. Syntheses of Azepinomycin, an Antitumor Antibiotic from Streptomyces Species, and Its 3-β-D-Ribofuranodise and Their 8-Imino Analogues
- Purines. LXI. An Attempted Synthesis of 2'-Deoxy-7-methyladenosine : Glycosidic Hydrolyses of the N^6-Methoxy Derivative and 2'-Deoxy N^x-methyladenosines
- Purines. LIX. An Alternative Synthesis of 7-Alkyl-1-methyladenines by Regioselective Alkylation, Fission, and Reclosure of the Adenine Ring
- Purines. LVIII. A Synthesis of 7-Alkyl-1-methyladenines from Adenosine by Regioselective Alkylation : Uilization of a 1-Methoxy Group as a Control Synthon
- Purines. LVII. Regioselective Alkylation of N^6,9-Disubstituted 8-Oxoadenines : Syntheses of the Sea Anemone Purine Caissarone and Some Positional Isomers and Analogues
- Purines. LIV. Intramolecular Cyclization of 9-Ethyl-1-(2-hydroxyethyl)adenine Caused by Nucleophiles : Formation of N^6,1-Ethanoadenine Derivatives
- Purines. LIII. Deamination of 1-(ω-Hydroxyalkyl)adenine Derivatives by Nucleophiles
- Purines. XLIX. Synthesis and Proton Nuclear Magnetic Resonance Study of 3,7-Dialkylxanthines and 1,3,7-Trialkylxanthines
- Purines. XLVIII. Syntheses and Proton Nuclear Magnetic Resonance Study of 2-Deuterioadenines Substituted or Unsubstituted at the 9-Position and of Their N-Oxygenated Derivatives
- Purines. XLVI. Preparation of 1-Ethyladenine from Adenosine
- Immunoliposome-Mediated Gene Transfer into Cultured Myotubes
- Examination of Local Anti-inflammatory Activities of New Steroids, Hemisuccinyl Methyl Glycolates
- Application of Sweet Potato Fiber to Skin Wound in Rat
- Gastroprokinetic Effect of a New Benzamide Derivative Itopride and Its Action Mechanisms in Conscious Dogs
- Synthesis of 5-(Alkylamino)-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamides : Key Intermediates for the Synthesis of 3-Alkyl-9-β-D-ribofuranosylpurine Derivatives
- Purines. XXXII. : Synthesis and Ring Fission of 3,9-Dialkyladenines
- Purines. XXV. Fission and Reclosure of the Adenine Ring by the Use of Modified Benzyloxy Groups at the 1-Position
- Purines. XXII. Methylation of 1-, 3-, 7-, 9-, and N^6-Methyladenines Bearing a Methoxyl Group at the N^6-Position : A Synthesis of 7,9-Dimethyladenine
- Purines. XX. Synthesis of 1-Substituted 5-Aminoimidazole-4-carboxamidines and Related Compounds
- Modification by Fluoride, Bromide, Iodide, Thiocyanate and Nitrite Anions of Reaction of a Myeloperoxidase-H_2O_2-Cl^- System with Nucleosides
- Effects of Fluvastatin and Its Major Metabolites on Low-Density Lipoprotein Oxidation and Cholesterol Esterification in Macrophages
- Fluvastatin, an HMG-CoA Reductase Inhibitor, Protects LDL from Oxidative Modification in Hypercholesterolemic Rabbits
- In Vitro Inhibitory Effects of the Optical Isomers and Metabolites of Fluvastatin on Copper Ion-Induced LDL Oxidation
- An in Vitro Study of the Hydroxyl Radical Scavengin Property of Fluvastatin, and HMG-CoA Reductase Inhibitor
- 2-(3-Pyridyl)thiazolidine-4-carboxamide Derivatives. III. Synthesis of Metabolites and Metabolism of 2-(3-Pyridyl)thiazolidine-4-carboxamides YM461 and YM264 as Platelet-Activating Factor (PAF) Receptor Antagonists
- Purines. XLVII. Dimroth Rearrangement versus Hydrolytic Deamination of 1-Ethyladenine
- 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
- Synthesis of the Selective 5-Hydroxytryptamine 4 (5-HT_4) Receptor Agonist (+)-(S)-2-Chloro-5-methoxy-4-[5-(2-piperidylmethyl)-1,2,4-oxadiazol-3-yl]aniline
- Intramolecular Oxymercuration with Mercuric Triflate
- Mercuric Triflate-TMU Catalyzed Hydration of Terminal Alkyne to give Methyl Ketone under Mild Conditions
- Effects of N-[2-(1-Azabicyclo[3,3,0]octan-5-yl)ethyl]2-nitroaniline Fumarate (SK-946), a Novel Cognition Activator, on Learning and Memory in Rodent Models
- Novel 5-Hydroxytryptamine 4 (5-HT_4) Receptor Agonists. Synthesis and Gastroprokinetic Activity of 4-Amino-N-[2-(1-aminocycloalkan-1-yl)ethyl]-5-chloro-2-methoxybenzamides
- Purines. XXXVII. : Synthesis and Reduction of 3,9-Diallkyladenine Salts Deuterated at the 2-Position : Their Use in the Proton Nuclear Magnetic Resonance Study of Isotopically Unmodified Species
- Purines.XXXIX. : The Crystal Structure of 9-Benzyl-N^6-methoxyadenine
- Purines. XXXI. : An X-Ray Crystallographic Structure Analysis of 3-Methyladenosine p-Toluenesulfonate
- Novel 5-Hydroxytryptamine (5-HT_3) Receptor Antagonists. Synthesis and Structure-Activity Relationships of 9-Methyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-4-one Derivatives
- Novel 5-Hydroxytryptamine (5-HT_3) Receptor Antagonists. IV. Synthesis and Pharmacological Evaluation of the Oxidation Products of (-)-(R)-5-[(1-Methyl-1H-indol-3-yl)carbonyl]-4,5,6,7-tetrahydro-1H-benzimidazole Hydrochloride (YM060 : Ramosetron)
- Novel 5-Hydroxytryptamine (5-HT_3) Receptor Antagonists. III. Pharmacological Evaluations and Molecular Modeling Studies of Optically Active 4,5,6,7-Tetrahydro-1H-benzimidazole Derivatives
- Novel 5-Hydroxytryptamine (5-HT_3) Receptor Antagonists. II. Synthesis and Structure-Activity Relationships of 4,5,6,7-Tetrahydro-1H-benzimidazole Derivatives
- Novel 5-Hydroxytryptamine (5-HT_3) Receptor Antagonists. I. Synthesis and Structure-Activity Relationships of Conformationally Restricted Fused Imidazole Derivatives
- Purines. XLIV. : A Kinetic Study of the Dimroth Rearrangement of the Marine Sponge Purine 1,9-Dimethyl-8-oxoadenine and Related Compounds
- Purines. XLIII. : A Total Synthesis of the Marine Sponge Base 6-Imino-1,9-dimethyl-8-oxopurine
- 53 桿菌tRNA構成成分,7-Methyladenosineの合成と加水分解(口頭発表の部)
- Purines. XLII. : Synthesis and Glycosidic Hydrolysis of 7-Alkyladenosines Leading to an Alternative Synthesis of 7-Alkyladenines
- Purines. XL. : Preparation of 9-(ω-Carboxyalkyl)-3-methyladenines
- Purines. XXXVI. : Fission and Reclosure of the Adenine Ring in 3,9-Disubstituted Adenines : Effects of Substituents
- Purines. XXXIV. : 3-Methyladenosine and 3-Methyl-2'-deoxyadenosine : Their Synthesis, Glycosidic Hydrolysis, and Ring Fission
- A General and Convenient Synthesis of 7-Alkyladenines from Adenine by Regioselective Alkylation Utilizing Blocking/Deblocking at the 3-Position
- Purines. XXVII. : Hydrolytic Deamination versus Dimroth Rearrangement in the 9-Substituted Adenine Ring : Effect of an ω-Hydroxyalkyl Group at the 1-Position
- Purines. XXVI. The Dimroth Rearrangement of 9-Substituted 1-Methyladenines : Accelerating Effect of a β-D-Ribofuranosyl Group at the 9-Position
- Purines. XXIV. Methylation of N^6-Alkoxyadenines and N^6-Methyladenine
- Purines. XXIII. Synthesis of N^6-Alkoxy-1,3-dialkyladeninium Salts and an Attempt to Synthesize 1,3-Dimethyladenine
- Purines. XIII. Ring Opening of 3-Alkyladenines with Carbobenzoxy Chloride : Transformation into 8-Hydroxylated Adenines
- Purines. X. A Convenient Method for Synthesis of 2', 3'-O-Isopropylidene-adenosine 1-Oxide
- Purines. XVIII. Kinetic Studies of the Dimroth Rearrangement of 1-Alkoxy-9-methyladenines and 1-Benzyloxyadenosine : Effect of 1-Benzyloxy and 9-β-D-Ribofuranosyl Groups on the Rates of the Ring-opening and the Reclosure
- Effect of a Novel Non-steroidal Anti-inflammatory Drug (M-5011) on Cytokine Levels in Rats With Monosodium Urate Crystal-Induced Pleurisy
- Purines. XI. The Synthesis of N-Alkoxyadenosines and Their 2', 3'-O-Isopropylidene Derivatives
- Cytotoxicity of Chlorinated Hydrocarbons and Lipid Peroxidation in Isolated Rat Hepatocytes (Proceedings of the 19th Symposium on Toxicology and Environmental Health)