標題: Azide-alkyne cycloaddition for universal post-synthetic modifications of nucleic acids and effective synthesis of bioactive nucleic acid conjugates
作者: Su, Yu-Chih
Lo, Yu-Lun
Hwang, Chi-Ching
Wang, Li-Fang
Wu, Min Hui
Wang, Eng-Chi
Wang, Yun-Ming
Wang, Tzu-Pin
生物科技學系
Department of Biological Science and Technology
公開日期: 2014
摘要: The regioselective post-synthetic modifications of nucleic acids are essential to studies of these molecules for science and applications. Here we report a facile universal approach by harnessing versatile phosphoramidation reactions to regioselectively incorporate alkynyl/azido groups into post-synthetic nucleic acids primed with phosphate at the 5\' termini. With and without the presence of copper, the modified nucleic acids were subjected to azide-alkyne cycloaddition to afford various nucleic acid conjugates including a peptide-oligonucleotide conjugate (POC) with high yield. The POC was inoculated with human A549 cells and demonstrated excellent cell-penetrating ability despite cell deformation caused by a small amount of residual copper chelated to the POC. The combination of phosphoramidation and azide-alkyne cycloaddition reactions thus provides a universal regioselective strategy to post-synthetically modify nucleic acids. This study also explicated the toxicity of residual copper in synthesized bioconjugates destined for biological systems.
URI: http://hdl.handle.net/11536/25105
http://dx.doi.org/10.1039/c4ob01132e
ISSN: 1477-0520
DOI: 10.1039/c4ob01132e
期刊: ORGANIC & BIOMOLECULAR CHEMISTRY
Volume: 12
Issue: 34
起始頁: 6624
結束頁: 6633
顯示於類別:期刊論文


文件中的檔案:

  1. 000341021400012.pdf

若為 zip 檔案,請下載檔案解壓縮後,用瀏覽器開啟資料夾中的 index.html 瀏覽全文。