PURINE NUCLEOSIDES .9. SYNTHESIS OF 9-BETA-D-RIBOFURANOSYL URIC ACID AND OTHER RELATED 8-SUBSTITUTED PURINE RIBONUCLEOSIDES
PURINE NUCLEOSIDES .9. SYNTHESIS OF 9-BETA-D-RIBOFURANOSYL URIC ACID AND OTHER RELATED 8-SUBSTITUTED PURINE RIBONUCLEOSIDES
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DOI：
10.1021/ja01086a028
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发表时间：
1965-01-01
影响因子：
15
通讯作者：
ROBINS, RK
中科院分区：
文献类型：
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作者：
HOLMES, RE;ROBINS, RK
以鸟苷为原料经几步反应合成了9-FI-O-呋喃核糖尿酸(IV)。该产品与从植物乳杆菌中分离得到的9-核糖基尿酸完全相同。将IV与Falconer和Gulland报告的从牛肉血液和肝脏中分离出的9-核糖基尿酸的数据进行比较，发现这些产品很可能是相同的。合成的其他8位含酮基的嘌呤核苷有2-氨基-9-呋喃核糖-6，8-嘌呤二酮(V)和6-氨基-9-8-D-呋喃核苷-8-嘌呤酮(XII)。水合肼和8-溴鸟苷回流得到8-氨基鸟苷(VII)，这是首次报道的8-氨基嘌呤核苷。以8-溴腺苷为原料，经8-叠氮腺苷催化还原生成8-氨基腺苷(IX)。讨论了这些新的嘌呤核糖核苷可能的生物化学意义。
The synthesis of 9-fi-O-ribofuranosyl uric acid (IV) has been accomplished in several steps from guanosine. This product is identical with 9-ribosyl uric acid isolated from Lactobacillus plantarum. Comparison of IV and the data available as reported by Falconer and Gulland for 9-ribosyl uric acid isolated from beef blood and liver reveals that these products are very likely the same. Other purine nucleosides synthesized containing a keto group at position 8 are 2-amino-9-fO-ribofuranosyl-6, 8-purinedione (V) and 6-amino-9-8-D-ribofuranosyl-8-purinone (XII). Refluxing aqueous hydrazine and 8-bromoguanosine yields 8-aminoguanosine (VII), the first reported 8-aminopurine nucleoside. 8-Aminoaden-osine (IX) was prepared from 8-bromoadenosine via 8-azidoadenosine which was converted to IX by catalytic reduction. The possiblebiochemical significance of these new purine ribonucleosides is discussed.