Journal
PURE AND APPLIED CHEMISTRY
Volume 80, Issue 8, Pages 1859-1871Publisher
WALTER DE GRUYTER GMBH
DOI: 10.1351/pac200880081859
Keywords
deoxyribozyme; PS-DNA; PS-RNA; nucleoside polyphosphates; hypophosphates
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Among the various classes of modified nucleotides and olioonucleotides, phosphorothioate analogs, in which the Sugar-phosphate backbone is modified by the substitution of a sulfur atom for one of the nonbridging oxygen atoms, have been most extensively Studied in both in vitro and in vivo experiments. However, this substitution induces P-chirality of the dinucleoside phosphorothioate moiety. Consequently, even short phosphorothioate oligonucleotides synthesized using standard chemical methods exist as mixtures of many diastereoisomers. In Our laboratory, the oxathiaphospholane (OTP) method has been developed for a stereocontrolled synthesis of oligo(deoxyribonucleoside phosphorothioate)s. Recently, this approach has been extended to ribonnucleoside derivatives, and stereodefined phosphorothioate diribonnucleotides were incorporated into oligomers suitable for mechanistic Studies on deoxyribozymes. Next, it was found that the OTP ring can be opened with nucleophiles as weak as the phosphate or pyrophosphate anion, giving rise to nucleoside (alpha-thiopolyphosphates. Surprisingly, the reaction between nucleoside OTP and O,O-dialkyl H-phosphonate or O,O-dialkyl H-phosphonothioate led to nucleoside 5'-O-(alpha-thio-beta-O,O-dialkyl-hypophosphate) or 5'-O-(alpha,beta-dithio-beta-O,O-dialkyl-liypophosphate), respectively, i.e., derivatives containing a direct P-P bond.
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