Synthesis of guanosine and its derivatives from 5-amino-1-beta-D- ribofuranosyl-4-imidazolecarboxamide. III. Formation of a novel cycloimidazole nucleoside and its cleavage reactions
Synthesis of guanosine and its derivatives from 5-amino-1-beta-D- ribofuranosyl-4-imidazolecarboxamide. III. Formation of a novel cycloimidazole nucleoside and its cleavage reactions
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从 5-氨基-1-β-D-呋喃核糖基-4-咪唑甲酰胺合成鸟苷及其衍生物。
DOI：
10.1093/nar/3.1.237
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发表时间：
1976
期刊：
影响因子：
--
通讯作者：
A. Yamazaki
中科院分区：
文献类型：
--
作者：
M. Okutsu;A. Yamazaki
将inch-anhydro-1-beta-D-ribofuranosyl-4-imidazolecarboxamide(5-amino-1-beta-D-ribofuranosyl-4-imidazolecarboxamide)与苯甲酰异硫氰酸酯反应，再与碘甲烷甲基化，合成了新的环咪唑核苷5-(1英寸-苯甲酰胺-1英寸-羟亚甲基)氨基-2‘，1-AICA(III)。根据其核磁共振波谱和化学反应确定了其结构。特别令人感兴趣的是III与各种亲核试剂的反应。例如，鸟苷(IX)是由III与氨水胺化得到的，产率为72%。III与甲胺和二甲胺的类似反应分别得到了N_2-甲基鸟苷(X)和N_2-二甲基鸟苷(XI)。III在碱性溶液中回流得到黄嘌呤(VII)。文中还讨论了III的可能形成和开环机制。
A new cycloimidazole nucleoside, 5-(1 inch -benzamido-1 inch-hydroxymethylene) amino-2', 1 inch-anhydro-1-beta-D-ribofuranosyl-4-imidazolecarboxamide (III) was synthesized by reaction of 5-amino-1-beta-D-ribofuranosyl-4-imidazolecarboxamide (AICA-riboside) with benzoyl isothiocyanate followed by methylation with methyl iodide. The structure of III was elucidated on the basis of its nmr spectra and chemical reactions. Of special interest are reactions of III with various nucleophiles. For example, guanosine (IX) was obtained by amination of III wtih ammonia in 72% yield. Analogous reactions of III with methylamine and dimethylamine gave N2-methylguanosine (X) and N2-dimethylguanosine (XI), respectively. Refluxing of III in alkaline solution afforded xanthosine (VII). The probable mechanism of formation and facile ring-opening of III is also discussed.