I. Barber et al., THE PROOLIGONUCLEOTIDE APPROACH .1. ESTERASE-MEDIATED REVERSIBILITY OF DITHYMIDINE-S-ALKYL-PHOSPHOROTHIOLATES TO DITHYMIDINE PHOSPHOROTHIOATES, Bioorganic & medicinal chemistry letters, 5(6), 1995, pp. 563-568
Alkylation of dithymidine phosphorothioate and phosphorodithioate with
various iodoalkyl acylates afforded the corresponding uncharged S-alk
yl phosphoromono- and di-thioates respectively. Upon incubation of the
se triesters in CEM cell extracts, the bioreversible alkyl acylate mas
king groups were selectively and rapidly removed by carboxyesterases p
resent in the milieu, yielding the starting dinucleoside diesters.