P-Stereodefined phosphorothioate analogs of glycol nucleic acids-synthesis and structural properties.

ABSTRACT: Enantiomerically pure, protected acyclic nucleosides of the GNA type (glycol nucleic acids) (^GN'), obtained from (R)-(+)- and (S)-(-)-glycidols and the four canonical DNA nucleobases (Ade, Cyt, Gua and Thy), were transformed into 3'-O-DMT-protected 2-thio-4,4-pentamethylene-1,3,2-oxathiaphospholane derivatives (OTP-^GN') containing a second stereogenic center at the phosphorus atom. These monomers were chromatographically separated into P-diastereoisomers, which were further used for the synthesis of P-stereodefined "dinucleoside" phosphorothioates ^GN_PST (^GN = ^GA, ^GC, ^GG, ^GT). The absolute configuration at the phosphorus atom for all eight ^GN_P

SUBMITTER: Tomaszewska-Antczak A 

PROVIDER: S-EPMC9082371 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature