98807-30-8Relevant academic research and scientific papers
A Chemical Strategy for Intracellular Arming of an Endogenous Broad-Spectrum Antiviral Nucleotide
Antczak, Nicole M.,Arnold, Jamie J.,Caldwell, Haley S.,Cameron, Craig E.,Ciota, Alexander T.,Harki, Daniel A.,Jose, Joyce,Narayanan, Anoop,Ngo, Kiet A.,Passow, Kellan T.,Sturla, Shana J.
, p. 15429 - 15439 (2021/11/12)
The naturally occurring nucleotide 3′-deoxy-3′,4′-didehydro-cytidine-5′-triphosphate (ddhCTP) was recently found to exert potent and broad-spectrum antiviral activity. However, nucleoside 5′-triphosphates in general are not cell-permeable, which precludes
A tractable and efficient one-pot synthesis of 5′-azido-5′- deoxyribonucleosides
Peterson, Theodore V.,Streamland, Tobin U. B.,Awad, Ahmed M.
, p. 2434 - 2444 (2014/03/21)
Synthetic routes to 5′-azidoribonucleosides are reported for adenosine, cytidine, guanosine, and uridine, resulting in a widely applicable one-pot methodology for the synthesis of these and related compounds. The target compounds are appropriate as precursors in a variety of purposive syntheses, as the synthetic and therapeutic relevance of azido- and amino-modified nucleosides is expansive. Furthermore, in the conversion of alcohols to azides, these methods offer a tractable alternative to the Mitsunobu and other more difficult reactions.
The aqueous N-phosphorylation and N-thiophosphorylation of aminonucleosides
Conway, Louis P.,Delley, Richard J.,Neville, Jonathan,Freeman, Gemma R.,Maple, Hannah J.,Chan, Vincent,Hall, Alexander J.,Hodgson, David R. W.
, p. 38663 - 38671 (2014/11/07)
We demonstrate N-phosphorylation and N-thiophosphorylation of unprotected aminonucleosides in aqueous media. N-Phosphorylations using phosphoric chloride and N-thiophosphorylations using thiophosphoryl chloride were explored as functions of pH using 5′-amino-5′-deoxyguanosine as substrate. These reagents were compared to phosphodichloridate and thiophosphodichloridate ions, and the methodology was applied to other aminonucleosides. S-Alkylations of the nucleoside N-thiophosphoramidates were investigated as functions of pH and alkylating agent. the Partner Organisations 2014.
A convenient synthesis of the cytidyl 3′-terminal monomer for solid-phase synthesis of RNG oligonucleotides
Awad, Ahmed M.,Collazo, Michael J.,Carpio, Kathrinna,Flores, Christina,Bruice, Thomas C.
experimental part, p. 3792 - 3794 (2012/09/10)
Replacing the phosphodiester backbone of RNA with positively charged guanidinium linkages has been shown to enable RNA oligomers to overcome electrostatic repulsion and bind double-stranded DNA in a triplex with high affinity. Ribonucleotide monomers with
General Approach to the Synthesis of Specifically Deuterium-Labeled Nucleosides
Voss, James J. De,Hangeland, Jon J.,Townsend, Craig A.
, p. 2715 - 2723 (2007/10/02)
Starting from D-(-)-ribose, a set of synthetic routes sharing common intermediates has been developed and exemplified in -, -, -, (5'R)--, and (5'S)--N4-benzoylcytidine and, by deoxygenation, their corresponding 2'-deoxynucleosides.These syntheses provide convenient access to millimolar quantities of deuterium/tritium-labeled natural or unnatural nucleosides for direct use or automated oligonucleotide synthesis.
