New efficient sulfurizing reagents for the preparation of oligodeoxyribonucleotide phosphorothioate analogues.
A set of new sulfurizing agents representing disulfides of arylsulfonic acids has been developed for the automated synthesis of phosphorothioate oligonucleotide analogues via the phosphoramidite method. These reagents, such as bis(benzenesulfonyl)disulfide, bis(p-toluenesulfonyl)disulfide, bis(p-methoxybenzensulfonyl)disulfide, and bis (p-chlorobenzenesulfonyl) disulfide, are easily prepared crystalline solid compounds. They are relatively inexpensive, easy to handle, and efficiently convert internucleotide cyanoethyl phosphite to the phosphorothioate triester within 1-2 min. The efficiency of phosphorothioate oligonucleotide synthesis with the use of these reagents is comparable to that of phosphodiester oligonucleotides.
D017739:Arylsulfonic Acids; D001483:Base Sequence; D004220:Disulfides / Q000138:chemical synthesis; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis*; D013873:Thionucleotides / Q000138:chemical synthesis*
D017739:Arylsulfonic Acids; D004220:Disulfides; D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides; D013873:Thionucleotides