THE PROOLIGONUCLEOTIDE APPROACH .1. ESTERASE-MEDIATED REVERSIBILITY OF DITHYMIDINE-S-ALKYL-PHOSPHOROTHIOLATES TO DITHYMIDINE PHOSPHOROTHIOATES

Citation
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
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
ISSN journal
0960894X
Volume
5
Issue
6
Year of publication
1995
Pages
563 - 568
Database
ISI
SICI code
0960-894X(1995)5:6<563:TPA.ER>2.0.ZU;2-M
Abstract
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.