Addressing regio- and stereo-specificity challenges in the synthesis of nucleoside 2',3'-cyclic monophosphate analogs - a rapid and facile synthesis of nucleoside-2',3'- O, O-phosphoro-thioate or -selenoate, and elucidation of the origin of the rare specificity

Molhm Nassir; Lara Balaom; Bilha Fischer

doi:10.1039/d0cc02886j

Addressing regio- and stereo-specificity challenges in the synthesis of nucleoside 2',3'-cyclic monophosphate analogs - a rapid and facile synthesis of nucleoside-2',3'- O, O-phosphoro-thioate or -selenoate, and elucidation of the origin of the rare specificity

Chem Commun (Camb). 2020 Oct 1;56(78):11633-11636. doi: 10.1039/d0cc02886j.

Authors

Molhm Nassir¹, Lara Balaom², Bilha Fischer¹

Affiliations

¹ Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel. bilha.fischer@biu.ac.il.
² Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, Bonn, Germany.

PMID: 32870217
DOI: 10.1039/d0cc02886j

Abstract

A new facile, rapid, stereo- and regio-selective one-pot synthesis of nucleoside-2',3'-O,O-phosphorothioate and selenoate analogs has been developed. This method avoids the need for protection strategies and chiral reagents, chiral metal catalysts, or chiral separations. This synthetic method has been applied to all natural nucleosides (U/A/G/C/T). Furthermore, we have deciphered the origin of the stereo- and regio-selectivity of the reaction.