首页 | 本学科首页   官方微博 | 高级检索  
     


Properties of Oligonucleotide with Phenyl-Substituted Carbocyclic Nucleoside Analogs for the Formation of Duplex and Triplex DNA
Authors:Tamer Nasr  Yosuke Taniguchi  Tomoko Takaki  Hidenori Okamura  Shigeki Sasaki
Affiliation:1. Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi , Higashi-ku , Fukuoka , Japan;2. Department of Pharmaceutical Chemistry , Faculty of Pharmacy, Helwan University, Helwan , Egypt;3. Department of Pharmaceutical Chemistry , Faculty of Pharmacy, King Khalid University , Kingdom of Saudi Arabia;4. Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi , Higashi-ku , Fukuoka , Japan
Abstract:(1S,3S,4R)-1-Phenyl-1-thymidyl-3-hydroxy-4-hydroxymethylcyclopentane (10) and their analogs were synthesized, incorporated into the oligodeoxynucleotides, and their properties were evaluated for the formation of duplex and triplex DNA. The known chiral cyclopentanone derivative was converted into the corresponding ketimine sulfonamide derivative, which was subjected to a stereoselective PhLi addition. The formed sulfonamide was hydrolyzed to afford the primary amino group, on which the thymine moiety was built. The benzyl protecting groups were removed to form the nucleoside analog having a phenyl group and the thymine unit at the 1′ position of a carbocyclic skeleton (10). In the estimation of the oligodeoxynucleotides incorporating 10 for duplex and triplex formation, the carbocyclic nucleoside analog 10 did not show the stabilizing effect for duplex formation; on the other hand, it stabilized the triplex. Therefore, the skeleton of the phenyl-substituted carbocyclic nucleoside analog 10 may be a platform for the formation of stable triplex DNA.
Keywords:Oligonucleotides  carbocyclic nucleoside analog  duplex DNA  triplex DNA  asymmetric synthesis
设为首页 | 免责声明 | 关于勤云 | 加入收藏

Copyright©北京勤云科技发展有限公司  京ICP备09084417号