Studies on stereospecific formation of P-chiral internucleotide linkage: synthesis of all-Rp and all-Sp methylphosphonate pentanucleotide d(MMTrAPMeTPMeTPMeCPMeTAc) via Grignard activated coupling.
Synthesis of stereoregular 3',5'-protected all-Rp and all-Sp methylphosphonate heterooligonucleotides d(MMTrAPMeTPMeTPMeCPMeTAc) (12) complementary to the fragment of HIV-1 splicing acceptor site was achieved via stereo-controlled formation of internucleotide linkage. The coupling was based on the transesterification of P-stereodefined monomer type of 5'-O-monomethoxytrityl-2'-O-deoxynucleoside 3'-O-[O-(4-nitrophenyl)methylphosphonate]. The nucleophile was a t-butylmagnesium chloride activated 5'-terminal hydroxyl function of the growing oligonucleotide chain. This and other P-homochiral oligomers will be used as building blocks for the synthesis of biologically significant, longer stereoregular oligonucleotides.
Jaworska-Maslanka
M M
MM
Polish Academy of Sciences, Department of Bioorganic Chemistry, Lodz, Poland.
Kacperczyk
W
W
Korczynski
D
D
Lesnikowski
Z
Z
D015497:HIV-1 / Q000235:genetics; D008968:Molecular Conformation; D009690:Nucleic Acid Conformation; D009838:Oligodeoxyribonucleotides; D016376:Oligonucleotides, Antisense / Q000138:chemical synthesis*; D013237:Stereoisomerism
D009838:Oligodeoxyribonucleotides; D016376:Oligonucleotides, Antisense; C021992:dideoxyribonucleoside methylphosphonates