33 プリンおよびピリミジンヌクレオシドのグリコシル転移
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概要
- 論文の詳細を見る
The alkyl and glycosyl groups of the purine derivatives were found to migrate from N-3 to N-9(N-7) position. The transfer of the glycosyl moiety of the pyrimidine nucleosides to the purine bases was carried out successfully. (Fig. 1) On heating in the presence of HX(X=C1, Br) 3-benzyl-N^6-benzoyl-adenine underwent the benzyl migration giving rise to the 9-benzyl derivative and a small amount of the 7-isomer. γ,γ-Dimethylallyl group of N^6-acyltriacanthine migrated under the same conditions to afford the 9-γ,γ-dimethylallyl derivative, whereas H_gX_2 caused the intramolecular rearrangement to give the 9-α,α-dimethylallyl ismer. (Fig. 2) The glycosyl migration of O,N^6-acyl-3-β-isoadenosine and its 5'-phosphate proceeded milder conditions. The 9-β-ribofuranosyl derivative was predominant in this migration reaction and the amount of α anomer depended on the catalyzer used. (Tab. 3) Similar migrations took place in cases of adenine, N^6,N^6-dimethyladenine and N^2-acetylguanine. (Tab. 1) These migration reactions were applied to the transglycosylation from pyrimidines to purines. When O,N-tetra-acylcytidine or -uridine was heated with N^6-acyladenine in the presence of the catalyzer, the ribosyl moiety of the acylated pyrimidine nucleoside migrated to N^6-acyladenine to yield O,N-tetra-acyladenosine. The derivatives of 3-isoadenosine, N^6,N^6-dimethyladenosine, inosine, guanosine and 7-ribofuranosylguanine were also obtained in good yields. (Tab. 5) Application of the transglycosylation reaction must pay a role in the preparation of purine nucleosides.
- 天然有機化合物討論会の論文
- 1967-09-25
著者
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宮木 美知子
Central Research Laboratories Sankyo Co. Ltd.
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清水 文治
三共中央研究所
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宮木 美知子
三共中央研究所
-
清水 文治
Central Research Laboratories Sankyo Co. Ltd.
関連論文
- N→N Alkyl and Glycosyl Migrations of Purines and Pyrimidines. IV. trans-Glycosylation from Pyrimidines to Purines. (A Novel Synthetic Method of Purine Nucleosides and Nucleotides)
- N→N Alkyl and Glycosyl Migration of Purines and Pyrimidines. III. N→N Alkyl and Glycosyl Migration of Purine Derivatives
- N→N Alkyl and Glycosyl Migration of Purines and Pyrimidines. II. Glycosyl Migration of 3-Glycosyl-N^6-acyladenine Derivatives
- N→N Alkyl and Glycosyl Migrations of Purines and Pyrimidines. I. A New Migration of 3-Alkyl-N^6-acyladenine
- Synthesis of Anomeric Pyrimidine Nucleoside 5'-Phosphates of L-Ribose, α-D-Cytidine 5'-Phosphate and 3-β-L-Ribofuranosyladenine 5'-Phosphate
- Studies on Synthetic Nucleotides. II. A Direct Synthetic Method of Ribonucleotides.
- 33 プリンおよびピリミジンヌクレオシドのグリコシル転移
- Alkyl Migration of 3-Alkylguanine Derivatives
- Systematic Analysis of Steroids. VI. Relationship between Steroid Structure and Mobility in Adsorption Liquid Phase Chromatography.
- Intermolecular Rearrangement of N'-Acyltriacanthine
- Preparation of L-β-Ribonucleosides and L-β-Ribonucleotides
- An Approach to Synthesis of Diterpenoid Alkaloids. IV.
- An Approach to Synthesis of Diterpenoid Alkaloids. III.
- An Approach to Synthesis of Diterpenoid Alkaloids. II.
- An Approach to Synthesis of Diterpenoid Alkaloids. I. Mannich Reaction of 2,6-Disubstituted Cyclohexanone.
- 23.ダイテルペンアルカロイド骨核の合成
- Studies on Synthetic Nucleotides. I. A Convenient Synthesis of Ribonucleotides.
- Studies on Synthetic Nucleosides V. Anomeric Pyrimidine Nucleosides of D-Arabinose and D-Lyxose
- A Convenient Synthesis of Nucleotides
- Studies on Synthetic Nucleosides. IV. A New Synthetic Method of Pyrimidine and Purine Ribosides
- A New Synthetic Method of Nucleosides
- Studies on Synthetic Nucleotides. IV. Preparation of L-β-Ribonucleosides and L-β-Ribonucleotides.
- A Convenient Synthesis of 1-β-D-Arabinofuranosylcytosine
- Studies on synthetic nucleotides-1,2,4-
- トリメチルシリル(TMS)化剤と有機合成(新しい試薬)