Stereochemical evidence for a phosphorylpyridinium intermediate in the iodine-mediated desulphurisation of a phosphorothioate diester
Cummins JH., Potter BVL.
Desulphurisation of (SP)-5′-O-(2′-deoxyadenosyl)- 3′-O-thymidyl phosphorothioate to 5′-O-(2′-deoxyadenosyl)- 3′-O-thymidyl [18O]phosphate proceeds with epimerisation at phosphorus using iodine in aqueous pyridine but with predominant inversion of configuration in aqueous 2,6-lutidine.