title: Studies on stereospecific formation of P-chiral internucleotide linkage: synthesis of all-Rp and all-Sp methylphosphonate pentanucleotide d(MMTrAPMeTPMeTPMeCPMeTAc) via Grignard activated coupling.
abstract: 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.
authors.affiliation: Polish Academy of Sciences, Department of Bioorganic Chemistry, Lodz, Poland.
authors.forename: M M
authors.initials: MM
authors.lastname: Jaworska-Maslanka
authors.forename: W
authors.initials: W
authors.lastname: Kacperczyk
authors.forename: D
authors.initials: D
authors.lastname: Korczynski
authors.forename: Z
authors.initials: Z
authors.lastname: Lesnikowski
mesh_terms: D015497:HIV-1 / Q000235:genetics; D008968:Molecular Conformation; D009690:Nucleic Acid Conformation; D009838:Oligodeoxyribonucleotides; D016376:Oligonucleotides, Antisense / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D009838:Oligodeoxyribonucleotides; D016376:Oligonucleotides, Antisense; C021992:dideoxyribonucleoside methylphosphonates