Key featuresShow Hide
- Creates phosphorothioate (PS) linkage in oligonucleotide backbone
- Soluble in acetonitrile
- Stable in solution for several months (a silanised bottle is not required)
- Exhibits high sulphurisation efficiency with both DNA and RNA
- Compatible with labile (fast) deprotection chemistry
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During synthesis using the phosphoramidite approach, the backbone of either DNA or RNA can be modified by sulphurisation (or sulphur-transfer) reagents to replace one non-bridging oxygen atom in the phosphodiester, thus creating a phosphorothioate (PS) linkage. This makes this method more suitable than H-phosphonate chemistry for controlling the state of each linkage [P=O versus P=S] in a site-specific manner.
EDITH has emerged as the reagent of choice for sulphurisation due to its all-round capability and ease of use. This product is soluble in acetonitrile, stable in solution for several months (a silanised bottle is not required), and exhibits high sulphurisation efficiency with both DNA and RNA. Its high efficiency in RNA synthesis, often unobtainable with other reagents, is of particular benefit, giving >99% sulphurisation efficiency.
EDITH also shows compatibility with labile (fast) deprotection chemistry. Some deleterious G modification has been observed, however this can be eliminated by using a modified coupling-capthio-cap cycle. This allows the preparation of certain phosphorothioates that may be sensitive to prolonged ammonium hydroxide solution treatment. However, it should be noted that capping prior to sulphurisation can lead to some oxidation of the PIII species.