Different reactivity of Sp and Rp isomers of phosphorothioate-modified oligonucleotides in a duplex structure.

Authors :: Islam MA
Fujisaka A
Kawakami J
Yamaguchi T
Obika S
Source :: Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2020 Jul 15; Vol. 30 (14), pp. 127166. Date of Electronic Publication: 2020 Apr 03.
Publication Year :: 2020
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.<br />Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.<br /> (Copyright © 2020. Published by Elsevier Ltd.)

Subjects :: Carbohydrate Conformation
Stereoisomerism
Phosphorothioate Oligonucleotides chemistry

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