一氯化碘促进了3-取代胸苷类似物的去糖基化、异头化和异构化。
Iodine monochloride facilitated deglycosylation, anomerization, and isomerization of 3-substituted thymidine analogues.
作者信息
Khalil Ahmed, Ishita Keisuke, Ali Tehane, Tiwari Rohit, Riachy Ramy, Toppino Antonio, Hasabelnaby Sherifa, Sayfullin Naum, Oliver Allen G, Gallucci Judith, Huang Zhenguo, Tjarks Werner
机构信息
a Division of Medicinal Chemistry & Pharmacognosy, College of Pharmacy , The Ohio State University , Columbus , Ohio.
出版信息
Nucleosides Nucleotides Nucleic Acids. 2014;33(12):786-99. doi: 10.1080/15257770.2014.945648.
The reaction of thymidine, 3-mono-, and 3,3',5'-trialkylsubstitued thymidine analogues with iodine monochloride (ICl) was investigated. Treatment with ICl resulted in rapid deglycosylation, anomerization, and isomerization of thymidine and 3-substituted thymidine analogues under various reaction conditions leading to the formation of the nucleobases as the major products accompanied by minor formation of α-furanosidic-, α-pyranosidic-, and β-pyranosidic nucleosides. On the other hand, 3,3',5'-trisubstitued thymidine analogues were only deglycosylated and anomerized. These results are similar to those observed for the acidic hydrolysis of the glycoside bond in nucleosides, but were presumably caused by the Lewis acid character of an iodine electrophile.
研究了胸苷、3-单烷基取代胸苷类似物和3,3',5'-三烷基取代胸苷类似物与一氯化碘（ICl）的反应。在各种反应条件下，用ICl处理导致胸苷和3-取代胸苷类似物快速去糖基化、异头异构化和异构化，生成碱基作为主要产物，并伴随少量α-呋喃糖苷、α-吡喃糖苷和β-吡喃糖苷核苷的生成。另一方面，3,3',5'-三取代胸苷类似物仅发生去糖基化和异头异构化。这些结果与核苷中糖苷键酸性水解的结果相似，但推测是由碘亲电试剂的路易斯酸性质引起的。
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