Synthesis of nucleoside phosphosulfates

Bioorganic & Medicinal Chemistry Letters
Joanna KowalskaJacek Jemielity

Abstract

We describe an efficient and scalable procedure for the chemical synthesis of nucleoside 5'-phosphosulfates (NPS) from nucleoside 5'-phosphorimidazolides and sulfate bis(tributylammonium) salt. Using this method we obtained various NPS with yields ranging from 70-90%, including adenosine 5'-phosphosulfate (APS) and 2',3'-cyclic precursor of 3'-phosphoadenosine 5'-phosphosulfate (PAPS), which are the key intermediates in the assimilation and metabolism of sulfur in all living organisms.

References

Dec 3, 2004·Drug Discovery Today·Virginia L RathStefan Hemmerich
Apr 30, 2008·Biochemistry and Cell Biology = Biochimie Et Biologie Cellulaire·Nahum Sonenberg
Aug 7, 2010·Tetrahedron·Rami A Al-Horani, Umesh R Desai

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Citations

Jan 25, 2017·Topics in Current Chemistry·Marcin WarminskiJacek Jemielity
Mar 19, 2019·Chemical Communications : Chem Comm·Daniel M GillAlan M Jones
Jul 17, 2015·Bioscience Reports·Anna M Wojdyła-Mamoń, Andrzej Guranowski
Oct 8, 2020·Scientific Reports·Jaber A AlshehriAlan M Jones
Mar 27, 2021·Nature Chemical Biology·Ryan W TibbleJohn D Gross
Mar 31, 2015·The Journal of Organic Chemistry·Marek R BaranowskiJacek Jemielity

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