Iodine monochloride facilitated deglycosylation, anomerization, and isomerization of 3-substituted thymidine analogues.
Iodine monochloride facilitated deglycosylation, anomerization, and isomerization of 3-substituted thymidine analogues.
复制标题
DOI：
10.1080/15257770.2014.945648
复制
发表时间：
2014
期刊：
影响因子：
--
通讯作者：
Tjarks W
中科院分区：
文献类型：
--
作者：
Khalil A;Ishita K;Ali T;Tiwari R;Riachy R;Toppino A;Hasabelnaby S;Sayfullin N;Oliver AG;Gallucci J;Huang Z;Tjarks W
研究了胸腺嘧啶核苷、3-单烷基和3，3‘，5’-三烷基取代胸苷类似物与一氯碘(ICL)的反应。在不同反应条件下，ICL可导致胸腺嘧啶核苷和3-取代胸腺嘧啶核苷类似物的快速脱糖、异构化和异构化，形成以碱基为主的产物，并伴随少量α-呋喃糖苷、α-吡喃糖苷和β-吡喃糖苷核苷的形成。另一方面，3，3‘，5’-三取代胸苷类似物仅被脱糖和异构化。这些结果类似于观察到的核苷中糖苷键的酸性水解，但推测是由碘亲和剂的Lewis酸性引起的。
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.
登录
查看更多内容
影响因子：
14.9
作者：
ARMSTRONG, VW;DATTAGUPTA, JK;SAENGER, W
通讯作者：
SAENGER, W
影响因子：
2.1
作者：
Jaime-Figueroa, S;Zamilpa, A;Morgans, DJ
通讯作者：
Morgans, DJ
影响因子：
4
作者：
DAS, CR;BOSE, AN
通讯作者：
BOSE, AN
影响因子：
2.6
作者：
Jin, Xuanye;Yang, Ruchun;Ju, Yong
通讯作者：
Ju, Yong
影响因子：
2.9
作者：
SHAPIRO, R;DANZIG, M
通讯作者：
DANZIG, M