Studies of Nucleosides and Nucleotides. LX. Purine Cyclonucleosides. (22). Synthesis of 8,5'-Anhydro-8-mercapto-9-β-D-arabinofuranosyladenine and 8,5'-Anhydro-8-mercapto-9-β-D-xylofuranosyladenine by the Rearrangement of O-Cyclonucleosides
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概要
- 論文の詳細を見る
8.2-Anhydro-9-β-D-arabinofuranosyladenine (I) was converted to 5'-tosyl derivative (II) in a yield of 75%. When Compound (II) was heated with sodium hydrogen sulfide in dimethylformamide (DMF) 8,5'-S-cyclonucleoside having arabinosyl configuration (IV) was obtained in a yield of 46%. From the ditosyl derivative (III) analogously a cyclonucleoside having 3'-tosyl group (VII) was obtained. 8,3'-Anhydro-9-β-D-xylofuranosyladenine (VIII) was converted to 5'-tosyl derivative (IX) and heated with sodium hydrogensulfide in DMF. In addition to a 8,5-S-cyclonucleoside of xylofuranosyl configuration (X), two compounds, 8,3'-anhydro-8-oxy-9-(5'-deoxy-5'-mercapto-β-D-xylofuranosyl) adenine disulfide (XI) and 5'-deoxy-5'-mercapto-8-oxy-9-β-D-xylofuranosyladenine (XII) was obtained. Compound (XII) was also obtained from X by the treatment with 0.01N sodium hydroxide. Thus, the OH group of xylo configuration in the sugar moiety of 8,5'-S-cyclonucleoside was found to be able to cleave the S-hydro linkage even in a mild condition.
- 公益社団法人日本薬学会の論文
- 1975-05-25
著者
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池原 森男
Faculty of Pharmaceutical Sciences, Osaka University(Present address)
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小木曽 雄子
Faculty Of Pharmaceutical Sciences Osaka University
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池原 森男
Faculty Of Pharmaceutical Sciences Osaka University
関連論文
- Activity of Artificial Mutant Variants of Human Growth Hormone Changes in Charged Residues around 62-67
- Activity of Artificial Mutant Variants of Human Growth Hormone Deficient in a Disulfide Bond between Cys53 and Cys165
- Synthesis of 8,5'-Anhydro-8-mercaptoadenosine
- Synthesis of 8,5'-Anhydro-8-mercaptoadenosine
- Synthesis of 8,5'-Anhydro-8-mercaptoadenosine
- Synthesis of 8,5'-Anhydro-8-mercaptoadenosine
- Studies on tRNA and Related Compounds. XXXVII. Synthesis and Physical Properties of 2'- or 3'-O-(o-Nitrobenzyl) nucleosides : the Use of o-Nitrophenyldiazomethane as a Synthetic Reagent
- Studies on Transfer Ribonucleic Acids and Related Compounds. XVI. Synthesis of Ribooligonucleotides using a Photosensitive o-Nitrobenzyl Protection for the 2'-Hydroxyl Group
- Studies on tRNA and Related Compounds. XXXVII. Synthesis and Physical Properties of 2'- or 3'-O-(o-Nitrobenzyl) nucleosides : the Use of o-Nitrophenyldiazomethane as a Synthetic Reagent
- Studies on Transfer Ribonucleic Acids and Related Compounds. XVI. Synthesis of Ribooligonucleotides using a Photosensitive o-Nitrobenzyl Protection for the 2'-Hydroxyl Group
- Molecular Dynamics and Free Energy Perturbation Calculations on the Mutation of Tyrosine 45 to Tryptophan in Ribonuclease T_1
- Synthesis and Expression of a Gene for Human Tumor Necrosis Factor
- Synthesis of a Gene Coding for Human Lysozyme
- Synthesis and Properties of d(ATACGCGTAT) and Its Derivatives Containing One and Two 5-Methylcytosine Residues. : Effect of the Methylation on Deoxyribonucleic Acid Conformation
- Polynucleotides. LXIII. Solution Conformation of Oligodeoxyribonucleotides containing an Alternating dC-dG Sequence which can form a Left-handed Double Helix
- Studies on Nucleosides and Nucleotides. LXXXVIII. : Purine Cyclonucleosides. XLIII. : ^C NMR Spectra of 2'-Substituted 2'-Deoxyadenosines. Substituent Effects on the Chemical Shifts in the Furanose Ring System
- Polynucleotides. LXI. Synthesis and Properties of Dinucleoside Monophosphates Containing 8,2'-S-Cycloadenosine and 8,2'-S-Cycloinosine Residues. Sequence Dependency of the Stability of the Stacking Conformation
- Polynucleotides. LV. Synthesis and Properties of Dinucleoside Monophosphates derived from Adenine 8,2'-S- and Uracil 6,2'-O-Cyclonucleosides. Further Support for the Left-Handed Stacking of Oligonucleotides having High-Anti Base Torsion Angles
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- Polynucleotides. LIII. Conformation of Dinucleoside Monophosphates containing 8-Methyladenosine Residue as studied by Proton Magnetic Resonance
- Studies on Nucleosides and Nucleotides. LXXXI. : Carbon-13 Magnetic Resonance Spectra of 8-Substituted Purine Nucleotides. Effects of Various Phosphate Groups on the Chemical Shifts and Conformation of Nucleotides
- Studies on Nucleosides and Nucleotides. LXXXVIII. : Purine Cyclonucleosides. XLIII. : ^C NMR Spectra of 2'-Substituted 2'-Deoxyadenosines. Substituent Effects on the Chemical Shifts in the Furanose Ring System
- Polynucleotides. LXI. Synthesis and Properties of Dinucleoside Monophosphates Containing 8,2'-S-Cycloadenosine and 8,2'-S-Cycloinosine Residues. Sequence Dependency of the Stability of the Stacking Conformation
- Polynucleotides. LV. Synthesis and Properties of Dinucleoside Monophosphates derived from Adenine 8,2'-S- and Uracil 6,2'-O-Cyclonucleosides. Further Support for the Left-Handed Stacking of Oligonucleotides having High-Anti Base Torsion Angles
- Polynucleotides. LIII. Synthesis and Properties of 2'-Azido-2'-deoxyadenylyl-(3'-5')-2'-azido-2'-deoxyadenosine
- Purification and Characterization of the Product of Chemically Synthesized Human Growth Hormone Gene Expression in Escherichia coli(Biological,Chemical)
- A Large-Scale Synthesis of a Nonadecadeoxyribonucleotide Duplex Having a Sequence Identical to That of Phage φ80 O_R2 by the Phosphoro-p-anisidate Method
- Studies on Transfer Ribonucleic Acids (tRNA) and Related Compounds. XLIX. Solid-Phase Synthesis of Nonadecaribonucleotide Corresponding to the 5'-Half of the Formylmethionine tRNA Deficient in D-Loop and Stem Region
- PARTIAL PURIFICATION AND BIOLOGICAL ACTIVITY OF THE PRODUCT OF CHEMICALLY SYNTHESIZED HUMAN GROWTH HORMONE GENE EXPRESSION IN ESCHERICHIA COLI
- Deoxyribonucleic Acids (DNA) and Related Compounds. XIII. Synthesis of DNA Duplexes Containing a Ribosome Binding Site
- Deoxyribonucleic Acids and Related Compounds. XII. Polymer Support Synthesis of a 46-mer Duplex Containing the Promoter of Galactose Operon of Escherichia coli
- Studies on Transfer Ribonucleic Acids and Related Compounds. XLIV. A Large-Scale Synthesis of the Anticodon Heptanucleotide of Formyl-methionine Transfer Ribonucleic Acid by Using 2'-O-Tetrahydrofuranylnucleosides
- Studies on Transfer Ribonucleic Acids and Related Compounds. XLIII. Synthesis of Oligoribonucleotides by using 5'-Selective Phosphorylation of 2'-O-Tetrahydrofuranyl Nucleosides
- Studies on Transfer Ribonucleic Acids and Related Compounds. XLI. Synthesis of tRNA Fragments containing Modified Nucleosides
- Studies on Deoxynucleic Acids and Related Compounds. VI. Synthesis of Oligodeoxyribonucleotides containing Recognition Sequences for Restriction Endonucleases
- Studies on Deoxynucleic Acids and Related Compounds. IV. Syntheses of an Octanucleotide containing a Recognition Site for Restriction Enzyme Eco RI and of an Arabinosyladenine Analog
- A NEW SYNTHETIC METHOD FOR 5'-TRIPHOSPHORYL-ADENYLYL-(2'-5')-ADENYLYL-(2'-5')-ADENOSINE (2-5A) AND 2-5A CORE USING 3'-O-TETRAHYDROFURANYL-ADENOSINE DERIVATIVES
- Studies on Deoxyribonucleic Acids and Related Compounds. III. Synthesis of Oligodeoxyribonucleotides Complementary to the Anticodon Loop of Escherichia coli tRNA^_f by an Improved Triester Method
- Studies on Deoxyribonucleic Acids and Related Compounds. II. Synthesis of a Decanucleotide containing a Restriction Enzyme (PstI) Recognition Site
- Studies on Transfer Ribonucleic Acids and Related Compounds. XXXIV. Stepwise Diester or Partial Triester Synthesis of Penta-to Octanucleotides Corresponding to Residues 41-46,47-54,61-65 and 66-71 of tRNA^_f of E. coli
- Studies on Transfer Ribonucleic Acids and Related Compounds. XXV. Synthesis of E. coli tRNA^_f 5'-Terminal Tetranucleotide C-G-C-Gp and Its Sequence Analog U-G-C-Gp
- Studies on Transfer Ribonucleic Acids and Related Compounds. XVII. Studies on Protecting Groups of Trisubstituted Phosphates in the Synthesis of Ribooligonucleotides
- Deoxyribonucleic Acids and Related Compounds. XXII. : Synthesis of Genes for Human Nerve Growth Factor and Its Fused Protein
- Overproduction of Cellular and Activated Ha-ras Proteins by Mutating a Synthetic Gene(Biological,Chemical)
- Polynucleotides. XXXIV. Ultraviolet Absorption and Circular Dichroism of ApUpG Analogs containing Modified Adenosine Residues
- Studies of Nucleosides and Nucleotides. LVI. A Versatile Method for the Synthesis of 8-Mercaptoadenosine Nucleotides
- Studies of Nucleosides and Nucleotides. LV. Reaction of Cytidine 5'-Monophosphate with p-Toluenesulfonyl Chloride
- Studies of Nucleosides and Nucleotides. XXXII. Purine Cyclonucleosides. 3. Synthesis of 2'-Deoxy- and 3'-Deoxyadenosine from Adenosine
- Direct Evidence of the Interaction between Base and the Protective Group in the Sugar Moiety of Nucleosides
- Synthesis of 8-Hydroxypurine Nucleosides
- Studies of Nucleosides and Nucleotides. XXV. Purine Cyclonucleosides. 2. Synthesis of 5'-Deoxyguanosine via an 5', 8-Cyclonucleoside
- Studies on Coenzyme Analogs. XVII. A New Synthesis of Purine Nucleoside by the Condensation of Chloropyrimidine with Glucosylamine.
- Synthesis of 2'- and 3'-Deoxyinosines
- Synthesis of Thioinosine and Thio-AICA-riboside Analogs
- Synthesis of Thio-AICA, 6-Thioxanthine, Isoguanine Analogs, and Their Ribosides
- Studies on Coenzyme Analogs. XIII. Oxidation of Methylmercaptopurine and its Nucleoside by means of N-Chloro-and N-bromosuccinimide.
- Potential Antimetabolites. IV. Synthesis of 2,6-Bis-alkylthiopurine Ribosides and their Selective Substitution by Nucleophilic Reagents.
- Studies on Transfer Ribonucleic Acids and Related Compounds. VII. Synthesis and Properties of Cyclic Oligoadenylic Acids
- Structural Elucidation of Tubercidin
- Potential Antimetabolites. VI. An Improved Synthesis of 2-β-D-Ribofuranosyl-as-triazine-3,5 (2H, 4H)-dione (6-Azauridine).
- Potential Antimetabolites. II. Chemical Synthesis of 6-Azacytidine.
- Potential Antimetabolites. I. Selective Thiation of Uracil and 1,2,4-Triazine-3,5 (2H, 4H)-dione (6-Azauracil).
- Debenzylation Reaction of Benzylphosphoric Acid Esters
- Studies of Nucleosides and Nucleotides. LXXXIV. Purine Cyclonucleosides. XL. Cyclonucleosides derived from 5´-Deoxyadenosine
- Polymer Support Synthesis of Oligodeoxyribonucleotide with an Aminoethyl or Aminohexyl Group at the 5' End by the Phosphite-Triester Approach
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- Synthesis of Oligoribonucleotides via the Phosphite-Triester Approach on a Polymer Support
- Synthesis and Properties of Phosphoramidite Derivatives of MOdified Nucleosides
- Studies on Transfer Ribonucleic Acids and Related Compounds. XXXIX. Chemical Synthesis of Heptadeca- and Hexadecaribonucleotides corresponding to the 3'-Terminus of the tRNA^_f of E. coli
- Studies on Transfer Ribonucleic Acids and Related Compounds. XXXI. Synthesis of the 3', 5'-Bisphosphorylated Hexanucleotide corresponding to Bases (72-77) of tRNA^ from E. coli and Its Base Transition Analog
- Studies on Transfer Ribonucleic Acids and Related Compounds. XXI. : Synthesis and Properties of Guanine Rich Fragments from E. coli tRNA^_f 5'-End
- Studies on Transfer Ribonucleic Acid and Related Compounds. XIII. Synthesis of Trinucleoside Diphosphates, A-U-A and εA-U-A via a Triester Intermediate
- Studies of Nucleosides and Nucleotides. XXII. Phosphorylation of Adenosine using Borate Complex as Protecting Group for 2'-and 3'-Hydroxyl Groups.
- Studies on Coenzyme Analogs. XVII. A New Phosphorylating Agent, 2,6-Lupetidylphos-phorodichloridate, and Some Investigations on the Selective Phosphorylation.
- Studies on Transfer Ribonucleic Acids and Related Compounds. XXXVIII. A Rapid Method for the Synthesis of Ribooligonucleotides by using 3', 5'-Unsubstituted Nucleosides. Synthesis of a Hexanucleotide containing Anticodon Triplet of E. coli tRNA^_f.
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- Studies of Nucleosides and Nucleotides. XLII. Purine Cyclonucleosides. (9). Synthesis of Adenine Cyclonucleosides having 8,2'-and 8,3'-O-Anhydro Linkages
- Polynucleotides. XXIX. Synthesis of Deoxyribooligonucleotide Blocks by an Extraction Method
- Studies on Transfer Ribonucleic Acids and Related Compounds. XXVII. Linear and Cyclic Oligonucleotides obtained by Polymerization of Protected Ribonucleoside 3'-Phosphates
- Synthetic Studies of Potential Antimetabolites. VII. Evidences that the supposed 1-β-D-Ribofuranosyl-1H-imidazo [4,5-b] pyridine is actually 3-β-D-Ribofuranosyl-3H-imidazo [4,5-b] pyridine (1-Deazapurine Ribofuranoside)
- Syntheses and Properties of Several 4-Alkyl-or Arylsulfonylquinoline 1-Oxides
- Studies of Nucleosides and Nucleotides. LXXXI. Synthesis and Characterization of 8-Methyladenosine
- Studies of Nucleosides and Nucleotides. XXXIX. Synthesis of 8-Substituted Purine Nucleotides by the Direct Replacement Reactions
- Studies of Nuclesides and Nucleotides.XXXI.Reaction of Nitrous Acid with Mono- and Di-esters of Phosphoramidate
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- Studies of Nucleosides and Nucleotides. LXXXV. Purine Cyclonucleosides. (35). Synthesis of Purine Nucleosides having 2'-Azido and 2'-Amino Functions by Cleavage of Purine Cyclonucleosides
- Polynucleotides. XII. Synthesis and Properties of Dinucleoside Monophosphates containing 8-Bromoadenosine
- Polynucleotides. I. Formation of Internucleotidic Linkage by Means of Dimethylformamide-Thionyl Chloride Complex
- Studies of Nucleosides and Nucleotides. XXVI. Further Studies on the Chlorination of Inosine Derivatives with Dimethylformamide-Thionyl Chloride Complex
- Synthesis of 3'-5'-Internucleotidic Linkage by the Use of Dimethyl-formamide-Thionyl Chloride Complex as Condensing Agent
- Studies of Nucleosides and Nucleotides. LXVIII. Purine Cyclonucleosides. (29). Synthesis and Properties of O-Cyclonucleosides derived from Hypoxanthine, Mercaptopurine, Methylmer-captopurine and Purine
- Studies of Nucleosides and Nucleotides. LII. Purine Cyclonucleosides. (17). Synthesis and Properties of Cyclonucleosides derived from Inosine and Thioinosine
- Studies of Nucleosides and Nucleotides. L. Purine Cyclonucleosides. (14). Synthesis and Properties of Cyclonucleosides derived from 9-D-Xylofuranosyladenine
- Potential Antimetabolites. III. Synthesis of 5-Aminoimidazole-4-carboxthioamide and Nitro-1-β-D-ribofuranosylimidazoles.
- Selective Removal of Protecting Groups for Phosphomonoesters of Nucleotides by Anodic Oxidation
- Polynucleotides. XXVI. Synthesis of an AUG Analog, 8,2-Anhydro-8-oxy-9-β-D-arabinofuranosyladenine Phosphoryl-(3'-5')-uridylyl-(3'-5')-guanosine
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