title: A-hydroxyphosphonate oligonucleotides: a promising DNA type?
abstract: The synthesis of monomers (S)-1, (R)-1 and 2 derived from (5'S)-, (5'R)-2'-deoxythymidine-5'-C-phosphonic acids and 2',5'-dideoxythymidine-5'-C-phosphonic acids was elaborated. The protection of the 5'-hydroxyl by the methoxycarbonyl group was a key step of the synthesis. Prepared monomers were used for the solid-phase assembly of several types oligothymidylate 15-mers (S)-3, (S)-4, (S)-5, (R)-4 and (R)-5 containing the chiral 3'-O-P-CH(OH)-5'' internucleotide linkage. Their hybridization properties with dA15 and rA15 were studied as well as their resistance against nuclease cleavage.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic.
authors.forename: Sárka
authors.initials: S
authors.lastname: Králíková
authors.forename: Milos
authors.initials: M
authors.lastname: Budesínský
authors.forename: Ivan
authors.initials: I
authors.lastname: Rosenberg
mesh_terms: D004247:DNA / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D009690:Nucleic Acid Conformation; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D063065:Organophosphonates; D013936:Thymidine / Q000031:analogs & derivatives*
chemical_list: D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides; D063065:Organophosphonates; C074618:5'-deoxythymidine; D004247:DNA; D013936:Thymidine