Practical Synthesis of Wybutosine, the Hypermodified Nucleoside of Yeast Phenylalanine Transfer Ribonucleic Acid
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概要
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An improved synthesis of 3-β-D-ribofuranosylwybutine (2) has been achieved by the Wittig reaction between purine-7-carbaldehyde (8) and the phosphorane derived from (R)-2-[(methoxycarbonyl)amino]-3-(triphenylphos-phonio)propanoate (9), followed successively by methylation, hydrogenation, and deprotection. On the other hand, the minor nucleoside wybutosine of yeast tRNA^<Phe> was isolated on a scale of 80 μg by partial digestion of unfractionated tRNA (1g) with nuclease P_1, followed successively by reversed-phase column chromatography, complete digestion with nuclease P_1/alkaline phosphatase, and reversed-phase HPLC. Comparison of this nucleoside with 2 has unambiguously established that the structure of wybutosine is (αs)-α-[(methoxycarbonyl)-amino]-4,6-dimethyl-9-oxo-3-β-D-ribofuranosyl-4,9-dihydro-3H-imidazo[1,2-a]purine-7-butanoic acid methylester (2).
- 公益社団法人日本薬学会の論文
- 2002-04-01
著者
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ITAYA Taisuke
Faculty of Pharmaceutical Sciences, Kanazawa University
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KANAI Tae
Faculty of Pharmaceutical Sciences, Kanazawa University
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Kanai Tae
Faculty Of Pharmaceutical Sciences Kanazawa University
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Itaya Taisuke
Faculty Of Pharmaceutical Sciences Kanazawa University
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IIDA Takehiko
Faculty of Pharmaceutical Sciences, Kanazawa University
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Iida Takehiko
Faculty Of Pharmaceutical Sciences Kanazawa University
関連論文
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- Synthesis and Structure of the Hypermodified Nucleoside of Rat Liver Phenylalanine Transfer Ribonucleic Acid
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- Purines. LXXIV. Syntheses and Rearrangements of 8-Oxoadenines Monomethylated at the N^6-, 1-, and 3-Positions
- Purines. LXXII. Oxidation of N^6-Alkyladenines with m-Chloroperoxybenzoic Acid Leading to N^6-Alkyladenine 1-Oxides
- Purines. LXXI. Preparation and Alkylation of 7-Alkyladenine 1-Oxides : A General Synthesis of 1-Alkoxy-7-alkyladenines
- Reactions of oxalyl chloride with 1,2-cycloalkanediols in the presence of triethylamine
- Isomerization through Cleavage and Recombination of Imidazolide Linkage in the Condensed Tricyclic System Related to Hypermodified Bases of Phenylalanine Transfer Ribonucleic Acids
- Bamberger Fission and Reclosure of 1-Alkyl-5-(alkylamino)imidazole-4-carbonitriles Leading to Their 2-Oxo Derivatives
- Purines. LXXIII. Syntheses of 8-Alkoxy- and 8-Hydroxy-3-alkyladenines from 3-Alkyladenine 7-Oxides through 7-Alkoxy-3-alkyladenines
- Reaction of Phosgene with the Tricycle Related to the Minor Base of Phenylalanine Transfer Ribonucleic Acids
- Practical Synthesis of Wybutosine, the Hypermodified Nucleoside of Yeast Phenylalanine Transfer Ribonucleic Acid
- Studies towards the Synthesis of the Hypermodified Nucleoside of Rat Liver Phenylalanine Transfer Ribonucleic Acid : Improved Synthesis of the Base β-Hydroxywybutine
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