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5'-脱氧-8,5'-环腺苷和-肌苷的新合成：构象固定的嘌呤核苷（核苷和核苷酸。十六）

A new synthesis of 5'-deoxy-8,5'-cyclo-adenosine and -inosine: conformationally-fixed purine nucleosides (nucleosides and nucleotides. XVI).

作者信息

Matsuda A, Muneyama K, Nishida T, Sato T, Ueda T

出版信息

Nucleic Acids Res. 1976 Dec;3(12):3349-57. doi: 10.1093/nar/3.12.3349.

DOI:10.1093/nar/3.12.3349
PMID:1005121
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC343179/
Abstract

A versatile method for the synthesis of 5'-deoxy-8,5'-cycloadenosine, a conformationally-fixed "anti" type of adenosine, was presented. Irradiation of 2', 3'-O-isopropylidene-5'-deoxy-5'-phenylthioadenosine with 60W Hg vapor lamp afforded 2',3'-O-isopropylidene-5'-deoxy-8,5'-cycloadenosine in high yield. The use of other 5'-alkylthio derivatives also gave the cycloadenosine, though the yields were rather poor. Deacetonation of the cyclocompound with 0.1N HCl gave 5'-deoxy-8,5'-cycloadenosine. The cycloinosine derivative was similarly prepared. The nmr, mass and CD spectra of 5'-deoxy-8,5'-cycloadenosine were given and discussed with the previously reported results.

摘要

介绍了一种合成5'-脱氧-8,5'-环腺苷的通用方法，5'-脱氧-8,5'-环腺苷是一种构象固定的“反式”腺苷类型。用60W汞蒸气灯照射2',3'-O-异丙叉基-5'-脱氧-5'-苯硫基腺苷可高产率得到2',3'-O-异丙叉基-5'-脱氧-8,5'-环腺苷。使用其他5'-烷硫基衍生物也能得到环腺苷，不过产率相当低。用0.1N盐酸使环化合物脱乙酰基得到5'-脱氧-8,5'-环腺苷。环肌苷衍生物也用类似方法制备。给出了5'-脱氧-8,5'-环腺苷的核磁共振、质谱和圆二色光谱，并与先前报道的结果进行了讨论。

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本文引用的文献

1
[On the thio ether and S-oxide derivatives of adenosine].[关于腺苷的硫醚和S-氧化物衍生物]
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Novel pyrimidine nucleoside oxosulfonium ylides and their photolysis to 2,2'-methylenecyclonucleosides.
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Synthesis of 2',3'-O-isopropylidene-5'-keto-8,5'-cycloadenosine, a novel cyclonucleoside.新型环核苷2',3'-O-异亚丙基-5'-酮基-8,5'-环腺苷的合成
J Org Chem. 1972 Mar 10;37(5):795-7. doi: 10.1021/jo00970a028.
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Clarification of the ring-closure of certain 4,5-diaminopyrimidines to 6-substituted 8-alkylpurines.某些4,5-二氨基嘧啶环合生成6-取代-8-烷基嘌呤的阐明
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The photolysis of 5'-deoxyadenosylcobalamin under anaerobic conditions.5'-脱氧腺苷钴胺素在厌氧条件下的光解作用。
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Evidence for the conformation of enzyme-bound adenosine 5'-phosphate. Substrate and inhibitor properties of 8,5' -cycloadenosine 5'-phosphate with adenylate kinase, adenylate aminohydrolase, adenylosuccinate lyase, and 5'-nucleotidase.
Biochemistry. 1972 Dec 19;11(26):4965-9. doi: 10.1021/bi00776a014.

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