Different reactivity of Sp and Rp isomers of phosphorothioate-modified oligonucleotides in a duplex structure. Issue 14 (15th July 2020)

• Record Type: Journal Article
• Authors: Islam, Md Ariful; Fujisaka, Aki; Kawakami, Junji; Yamaguchi, Takao; Obika, Satoshi
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 30:Issue 14(2020)
• Publication Date: 2020-07-15
• Subjects: Phosphorothioate -- Oligonucleotide -- Alkylation reaction -- Stereoselectivity; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2020.127166
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: The presence of a stereoisomeric center at the phosphorus atom in phosphorothioate-modified oligonucleotides (PS-ONs) has been recognized as an important feature since the early stages of their development. Therefore, several studies have been conducted on the chirality of PS-ONs. In this study, we evaluated the stereo-biased chemistry of PS-ON duplexes. Depending on their absolute configurations, PS-ON duplexes were found to have significantly different and stereospecific reactivities towards simple alkylating reagent.