Diastereomeric Process Control in the Synthesis of 2′-O-(2-Methoxyethyl) Oligoribonucleotide Phosphorothioates as Antisense Drugs

Coupling of 2′-O-methoxyethylsubstituted nucleoside phosphoramidites to 5′-hydroxyl group of a nucleoside or nucleotide on solid support is under stereochemical process control and is independent of scale, concentration, synthesizer, ratio of amidite diastereomers, solid support etc. However, activa...

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Bibliographic Details
Published in:Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2003-10, Vol.22 (5-8), p.1639-1645
Main Authors: Ravikumar, Vasulinga T., Cole, Douglas L.
Format: Article
Language:English
Subjects:
Activators
Base Sequence
Coupling
Drug Design
Indicators and Reagents
Magnetic Resonance Spectroscopy
Oligomerization
Oligonucleotides - chemical synthesis
Oligonucleotides - chemistry
Oligonucleotides - therapeutic use
Organophosphorus Compounds
Phosphate protecting group
Phosphates
Process control
RNA, Antisense - chemical synthesis
RNA, Antisense - chemistry
RNA, Antisense - therapeutic use
Stereochemistry
Stereoisomerism
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Description
Summary:Coupling of 2′-O-methoxyethylsubstituted nucleoside phosphoramidites to 5′-hydroxyl group of a nucleoside or nucleotide on solid support is under stereochemical process control and is independent of scale, concentration, synthesizer, ratio of amidite diastereomers, solid support etc. However, activators and phosphate protecting groups do play a role in influencing the ratio of phosphorothioate diesters obtained by sulfurization of phosphite triesters.
ISSN:1525-7770
1532-2335
DOI:10.1081/NCN-120023089