Attempted stereoselective synthesis of P-chiral analogues of oligodeoxyribonucleotides.
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.
Jaworska
M
M
Polish Academy of Sciences, Department of Bioorganic Chemistry, Sienkiewicza, Poland.
Leśnikowski
Z J
ZJ
Stec
W J
WJ
D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013873:Thionucleotides / Q000138:chemical synthesis
D009838:Oligodeoxyribonucleotides; D013873:Thionucleotides