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

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

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,

^a Lara Balaom^b and Bilha Fischer*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel
E-mail: bilha.fischer@biu.ac.il
Fax: 972-3-6354907
Tel: 972-3-5318303

^b Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, Bonn, Germany

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.

Download options Please wait...

Supplementary files

Supplementary information PDF (1467K)

Article information

DOI: https://doi.org/10.1039/D0CC02886J
Article type: Communication
Submitted: 28 Apr 2020
Accepted: 14 Jul 2020
First published: 16 Jul 2020

Download Citation

Chem. Commun., 2020,56, 11633-11636

Permissions

Request permissions

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

M. Nassir, L. Balaom and B. Fischer, Chem. Commun., 2020, 56, 11633 DOI: 10.1039/D0CC02886J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Chemical Communications

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†

Abstract

Supplementary files

Article information

Download Citation

Permissions

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

Social activity

Search articles by author

Spotlight

Advertisements