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Sulfur-Transfer Reagents for Synthesis of Oligonucleotide Phosphorothioates
DNA and RNA phosphorothioates have attracted attention as novel therapeutic agents through antisense mechanism of action and because of their nuclease resistance.1) Beaucage reagent (1),2) bis(phenylacetyl) disulfide (2)3) and xanthane hydride (3)4,5) are widely used as sulfur-transfer reagents for the synthesis of oligonucleotide phosphorothioates via the phosphoramidite method. In particular, 3 has the advantages that it does not yield oxidants leading to side reactions and generating toxic substances such as carbon disulfide or cyanamide, as byproducts.
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References
- 1)Nucleic acid therapeutics: basic concepts and recent developments
- 2)3H-1,2-Benzodithiol-3-one 1,1-dioxide
- 3)Phosphorothioate Oligonucleotides with Low Phosphate Diester Content: Greater than 99.9% Sulfurization Efficiency with “Aged” Solutions of Phenylacetyl Disulfide (PADS)
- 4)Large-Scale Synthesis of Oligonucleotide Phosphorothioates Using 3-Amino-1,2,4-dithiazole-5-thione as an Efficient Sulfur-Transfer Reagent
- 5)Mechanism of the sulfurisation of phosphines and phosphites using 3-amino-1,2,4-dithiazole-5-thione (xanthane hydride)
