31P NMR Study of the Desulfurization of Oligonucleoside Phosphorothioates Effected by “Aged” Trichloroacetic Acid Solutions
The Journal of Organic Chemistry2005Vol. 70(8), pp. 3303–3306
Citations Over Time
Jacek Cieślak, Cristina Ausín, Marcin K. Chmielewski, Jon S. Kauffman, John K. Snyder, Alfred Del-Grosso, Serge L. Beaucage
Abstract
When employing phosphoramidites 1a-d in the solid-phase synthesis of oligonucleoside phosphorothioates, the thermolytic 2-[N-methyl-N-(2-pyridyl)]aminoethyl thiophosphate protecting group is lost to a large extent during the course of the synthesis. The resulting phosphorothioate diesters are then substantially desulfurized upon recurring exposure to a commercial solution of deblocking reagent during chain assembly. This problem is caused by the secondary decomposition product(s) of the reagent and is alleviated by using a fresh solution of the deblocking reagent prepared from solid trichloroacetic acid.
Related Papers
- → Phosphate Esters, Thiophosphate Esters and Metal Thiophosphates as Lubricant Additives(2013)121 cited
- → Thiophosphate and thiophosphonate analogues of glucose-1-phosphate: synthesis and enzymatic activity with a thymidylyltransferase(2013)15 cited
- → THE INSECTICIDAL ACTIVITY OF PARATHION, ITS ISOMERS AND SOME RELATED COMPOUNDS(1951)9 cited
- → The inhibitory effect of thiophosphate on the adenosine triphosphate-inorganic phosphate exchange reaction of rat liver mitochondria(1963)4 cited
- → A Convenient Synthesis of S‐[(2R)‐2‐Acetamido‐3‐(hexadecyloxy)propyl] 2‐(Trimethylammonio)ethyl Thiophosphate, a New Amido‐Thiophosphate Analog of PAF(1996)3 cited