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Synthesis of High-Quality Antisense Drugs. Addition of Acrylonitrile to Phosphorothioate Oligonucleotides: Adduct Characterization and Avoidance
It is demonstrated that the acrylonitrile (AN) generated during the ammonolysis step of oligonucleotide manufacture selectively adds to thymine residue present in ISIS 2302 to give a full-lengthExpand
Controlled Detritylation of Antisense Oligonucleotides
The last chemical step in standard oligonucleotide synthesis, the acid-catalyzed removal of 4,4‘-dimethoxytrityl (DMTr) protecting groups from the 5‘-terminus of oligonucleotides is accompanied byExpand
Synthesis of an antisense oligonucleotide targeted against C-raf kinase: efficient oligonucleotide synthesis without chlorinated solvents.
It is demonstrated that a solution of dichloroacetic acid in toluene removes dimethoxytrityl groups from the 5'-terminus of an antisense phosphorothioate oligodeoxyribonucleotide (ISISExpand
Purification of antisense oligonucleotides.
AX provides a way to scale up production on somewhat less expensive equipment with reduced organic solvent requirements, and can also give high-purity products at generally higher media capacities. Expand
Solid Phase Synthesis of Phosphorothioate Oligonucleotides Utilizing Diethyldithiocarbonate Disulfide (DDD) as an Efficient Sulfur Transfer Reagent
Abstract Diethyldithiodicarbonate (DDD), a cheap and easily prepared compound, is found to be a rapid and efficient sulfurizing reagent in solid phase synthesis of phosphorothioateExpand
Chemical Synthesis and Purification of Phosphorothioate Antisense Oligonucleotides
Over a dozen antisense oligonucleotide drugs are undergoing human clinical trials for the treatment of viral infections, cancers, and a range of inflammatory disorders (Table 1). One of these wasExpand
Applications of green chemistry in the manufacture of oligonucleotide drugs
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 accomplishmentsExpand
Large-Scale chromatographic purification of ougonucleotides
Summary There are two robust single-step methods for purification of synthetic oligonucleotides at any scale, as shown in this chapter. RP purification is thehigh-throughput small-scale application.Expand
Influence of Diastereomeric Ratios of Deoxyribonucleoside Phosphoramidites on the Synthesis of Phosphorothioate Oligonucleotides
Abstract Extensive investigations on the influence of diastereomeric ratios of deoxyribonucleoside phosphoramidites on stereo-reproducibility of solid phase synthesis of phosphorothioateExpand
Dimethoxytrityl Removal in Organic Medium: Efficient Oligonucleotide Synthesis Without Chlorinated Solvents
Abstract Oligonucleotides are finding widespread utility in various applications in diagnostics and molecular biology and as therapeutic agents. In standard synthesis of such oligonucleotides throughExpand