88751-25-1Relevant academic research and scientific papers
Synthesis and properties of novel l-isonucleoside modified oligonucleotides and siRNAs
Zhang, Jun,Chen, Yue,Huang, Ye,Jin, Hong-Wei,Qiao, Ren-Ping,Xing, Lei,Zhang, Liang-Ren,Yang, Zhen-Jun,Zhang, Li-He
, p. 7566 - 7577,12 (2012)
Antisense oligonucleotides and siRNAs are potential therapeutic agents and their chemical modifications play an important role to improve the properties and activities of oligonucleotides. Isonucleoside is a type of nucleoside analogue, in which the nucleobase is moved from C-1 to other positions of ribose. In this report, a novel isonucleoside 5 containing a 5′-CH 2-extended chain at the sugar moiety was synthesized, thus isoadenosine 5a and isothymidine 5b were incorporated into a DNA single strand and siRNA. It was found that isonucleoside 5 modified oligonucleotides can form stable double helical structures with their complementary DNA and RNA and the stability towards nuclease and ability to activate RNase H are more promising compared with the unmodified, natural analogues. In siRNA, passenger strand modified with isonucleoside (5a/b) at 3′ or 5′ terminal can retain the silencing activity and minimize the passenger strand specific off-target effect.
Synthesis of 2S-(2-hydroxyethyl)-3R-hydroxy-4S-(thymin-1-yl or adenin-9-yl)-tetrahydrofuran
Liu, Ying-Chun,Zhang, Jun,Xing, Lei,Yang, Zhen-Jun,Zhang, Liang-Ren,Zhang, Li-He
, p. 9630 - 9635 (2008/12/22)
Two synthetic strategies were developed to obtain isonucleosides 2a and 2b. Starting from the known compound 4, an extension of one carbon unit at sugar 6-terminal was achieved by Wittig reaction and Stannyl-desulfonylation reaction. After oxidation of th
