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Attempted stereoselective synthesis of P-chiral analogues of oligodeoxyribonucleotides
M Jaworska1, Z J Leśnikowski, W J Stec
1Polish Academy of Sciences, Department of Bioorganic Chemistry, Sienkiewicza, Poland.
Nucleic Acids Symposium Series
|January 1, 1989
Abstract:
Reaction of diastereomeric 5'MMT-nucleoside 3'-O-(4-nitrophenylmethanephosphate) or 3'-O-[O-(4-nitrophenyl)-S-(2-nitrobenzyl)phosphorothioate] with tBuMgCl-activated, 3'-protected nucleoside is stereospecific and leads, after appropriate work-up, to dinucleoside-3',5'-methanephosphonate or dinucleoside-3',5'-phosphorothioate, respectively. This procedure extended to 5'-activated nucleotides, allows to prepare short, stereoregular oligonucleotide analogues bearing at internucleotide positions methanephosphonate or phosphorothioate function of predetermined sense of chirality at P-centers.