Wojciech J. Stec

Reversed-phase high-performance liquid chromatographic separation of diastereomeric phosphorothioate analogues of oligodeoxyribonucleotides and other backbone-modified congeners of DNA.

Diastereomeric phosphorothioate analogues of oligodeoxyribonucleotides, which were synthesized by an automated, solid-phase, phosphoramidite-coupling method, were conveniently separated by reversed-phase high-performance liquid chromatography on a muBondapak C18 column with a gradient of acetonitrile in triethylammonium acetate buffer. These synthetic and chromatographic methods were also used to obtain diastereomerically pure bis-phosphorothioate, alkanephosphonate, and O-alkyl phosphotriester analogues of DNA for exploratory studies of stereochemistry and phosphorolytic enzymes.

Stereochemical studies of the formation of chiral internucleotide linkages by phosphoramidite coupling in the synthesis of oligodeoxyribonucleotides

HPLC-fractionated (Rp)- and (Sp)-phosphoramidites underwent tetrazole-catalyzed coupling to support-bound nucleosides to give intermediary phosphates with epimerization at phosphorus, as shown by conversion to epimerized mixtures of dinucleoside phosphorothioates.

Synthesis, separation, and stereochemistry of diastereomeric oligodeoxyribonucleotides having a 5′-terminal internucleotide phosphorothioate linkage

Abstract An automated, solid-phase, phosphoramidite-coupling method provided the title compounds, up to a hexadecamer, for HPLC isolation of diastereomerically pure samples, and comparative digestions with snake venom phosphodiesterase and nuclease P1.