Practical synthesis of wybutosine, the hypermodified nucleoside of yeast phenylalanine transfer ribonucleic acid

被引：6

作者：

Itaya, T ^{[1
]}

Kanai, T ^{[1
]}

Iida, T ^{[1
]}

机构：

[1] Kanazawa Univ, Fac Pharmaceut Sci, Kanazawa, Ishikawa 9200934, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2002年 / 50卷 / 04期

关键词：

wybutosine; minor nucleoside; yeast tRNA(Phe); fluorescent nucleoside; condensed tricyclic nucleoside; H-1-NMR;

D O I：

10.1248/cpb.50.530

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

An improved synthesis of 3-beta-D-ribofuranosylwybutine (2) has been achieved by the Wittig reaction between 4,6-dimethyl-9-oxo-3-[2,3,5-tris-O-(tert-butyldimethylsilyl)-beta- D-ribofuranosyl]-4,9-dihydro-3H-imidazo [1,2-a]-purine-7-carbaldehyde (8) and the phosphorane derived from (R)-2-[(methoxycarbonyl)amino]-3-(triphenylphosphonio)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 mug by partial digestion of unfractionated tRNA (1 g) 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 (alphaS)-alpha-[(methoxycarbonyl)-amino] -4,6-dimethyl-9-oxo-3-beta-D-ribofuranosyl-4,9-dihydro-3H-imidazo[1,2-a]purine-7-butanoic acid methyl ester (2).

引用

页码：530 / 533

页数：4

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