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Synthesis and absolute configuration of P-chiral O-isopropyl oligonucleotide triesters

✍ Scribed by Wojciech J. Stec; Gerald Zon; Kathleen A. Gallo; R.Andrew Byrd; Bogdan Uznanski; Piotr Guga

Book ID
104229111
Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
306 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis

New (J-isopropylphosphomorpholidite reagents provided the title compounds as mixtures of P-chiral diastereomers, which were separated by HPLC for enzymatic digestion studies and assignment of configuration at phosphorus by chemical correlation with known phosphorothioates. Among the synthetic analogues of oligodeoxyribonucleotides, those having alkylated internucleotide phosphate moieties (1, DNA triesters) are especially interesting. In addition to their relevance as products of DNA alkylation, synthetic 1 are resistant to nucleases and are _ taken up by cells, which makes them candidates for antiviral drugs and drug-carriers. 2 Consequently, our investigations of backbone-modified DNA analogues, such as phosphorothioates 3-5 and alkanephosphonates, 6 have led to the presently described synthesis of isopropoxy 1 (J-OiPr)

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