Critical Effect of Base Pairing of Target Pyrimidine on the Inter-strand Photo-cross-linking of DNA via 3-Cyanovinylcarbazole Nucleoside
Critical Effect of Base Pairing of Target Pyrimidine on the Inter-strand Photo-cross-linking of DNA via 3-Cyanovinylcarbazole Nucleoside
复制标题
目标嘧啶碱基配对对 3-氰基乙烯基咔唑核苷 DNA 链间光交联的关键影响
DOI：
10.1021/acs.bioconjchem.5b00352
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发表时间：
2015
影响因子：
4.7
通讯作者：
Kenzo Fujimoto
中科院分区：
文献类型：
--
作者：
Takashi Sakamoto;Minako Ooe;Kenzo Fujimoto
为了评估目标嘧啶的碱基配对对DNA通过3-氰紫酰咔唑核苷（CNVK）进行链间光交联反应的影响，将目标嘧啶的互补碱基替换为非规范嘌呤碱基或1,3-丙二醇(S)。由于靶化合物C的碱基对中氢键的减少明显加快了光交联反应的速度（3.6 ~ 7.7倍），可见靶化合物嘧啶的碱基对中氢键的数目，即碱基对的稳定性对链间光交联反应起着关键作用。在G - S取代的情况下，cnvk对C的光反应活性最高，其光反应速率常数（k= 2.0 S - 1）与cnvk对T与A配对的光反应速率常数（k= 3.5 S - 1）相当。这是序列特异性链间光交联中对C最活跃的光交联反应。这可能有助于设计用于各种靶序列的光交联寡脱氧核糖核苷酸。
To evaluate the effect of base pairing of the target pyrimidine on the interstrand photo-cross-linking reaction of DNA via 3-cyanovinylcarbazole nucleoside (CNVK), a complementary base of target pyrimidine was substituted with noncanonical purine bases or 1,3-propandiol (S). As the decrease of the hydrogen bonds in the base pairing of target C accelerated the photo-cross-linking reaction markedly (3.6- to 7.7-fold), it can be concluded that the number of hydrogen bonds in the base pairing, i.e., the stability of base pairing, of the target pyrimidine plays a critical role in the interstrand photo-cross-linking reaction. In the case of G to S substitution, the highest photoreactivity toward C was observed, whose photoreaction rate constant (k= 2.0 s–1) is comparable to that ofCNVK toward T paired with A (k= 3.5 s–1). This is the most reactive photo-cross-linking reaction toward C in the sequence specific interstrand photo-cross-linking. This might facilitate the design of the photo-cross-linkable oligodeoxyribonucleotides for various target sequences.