scholarly journals Solid-Phase Synthesis of Boranophosphate/Phosphorothioate/Phosphate Chimeric Oligonucleotides and Their Potential as Antisense Oligonucleotides

2021 ◽  
Author(s):  
Yuhei Takahashi ◽  
Kazuki Sato ◽  
Takeshi Wada
Keyword(s):  
Antisense Oligonucleotides ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Chimeric Oligonucleotides

scholarly journals Solid-Phase Synthesis of Phosphorothioate/Phosphonothioate and Phosphoramidate/Phosphonamidate Oligonucleotides

Molecules ◽  
2019 ◽  
Vol 24 (10) ◽  
pp. 1872 ◽  
Author(s):  
Ondřej Kostov ◽  
Radek Liboska ◽  
Ondřej Páv ◽  
Pavel Novák ◽  
Ivan Rosenberg
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
The Novel ◽  
Phase Synthesis ◽  
Chimeric Oligonucleotides ◽  
Modified Oligonucleotide

We have developed a robust solid-phase protocol which allowed the synthesis of chimeric oligonucleotides modified with phosphodiester and O-methylphosphonate linkages as well as their P-S and P-N variants. The novel O-methylphosphonate-derived modifications were obtained by oxidation, sulfurization, and amidation of the O-methyl-(H)-phosphinate internucleotide linkage introduced into the oligonucleotide chain by H-phosphonate chemistry using nucleoside-O-methyl-(H)-phosphinates as monomers. The H-phosphonate coupling followed by oxidation after each cycle enabled us to successfully combine H-phosphonate and phosphoramidite chemistries to synthesize diversely modified oligonucleotide strands.

Applications of green chemistry in the manufacture of oligonucleotide drugs

2001 ◽  
Vol 73 (1) ◽  
pp. 175-180 ◽  
Author(s):  
Yogesh S. Sanghvi ◽  
V. T. Ravikumar ◽  
Anthony N. Scozzari ◽  
Douglas L. Cole
Keyword(s):  
Green Chemistry ◽  
Cost Efficiency ◽  
Antisense Oligonucleotides ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Support ◽  
Protecting Groups ◽  
Atom Economy ◽  
Phase Synthesis ◽  
Toxic Materials

We have modified the current phosphoramidite-based, solid-phase synthesis of antisense oligonucleotides to accommodate principles of green chemistry. In this article, we summarize key accomplishments that reduce or eliminate the use or generation of toxic materials, solvents, and reagents. Also discussed are methodologies that allow reuse of valuable materials such as amidites, solid-support, and protecting groups, thus improving the atom economy and cost-efficiency of oligonucleotide manufacture. Approaches to accident prevention and the use of safer reagents during oligonucleotide synthesis are also covered.

Solid-phase synthesis of 5′-triantennary N-acetylgalactosamine conjugated antisense oligonucleotides using phosphoramidite chemistry

2015 ◽  
Vol 25 (19) ◽  
pp. 4127-4130 ◽  
Author(s):  
Thazha P. Prakash ◽  
W. Brad Wan ◽  
Audrey Low ◽  
Jinghua Yu ◽  
Alfred E. Chappell ◽  
...  
Keyword(s):  
Antisense Oligonucleotides ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Phosphoramidite Chemistry
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