'Ethylene-bis[phosphonate] nucleic acids': novel monomeric synthons for the solid-phase synthesis of (P-CH2-CH2-P)-bridged oligonucleotides.
An efficient synthesis of modified deoxyribonucleosidic building units, containing the 'ethylene-bisphosphonate nucleic acids' (EBPNAs) 1 or 2, has been developed. By means of solution-phase incorporation of 11, the oxidized form of 2, dinucleotide analogs of type 13 were prepared. The same strategy was used to incorporate 2 into the 5'-terminal position of the 12-mer homopolynucleotide methylphosphonate 14. A preliminary approach for solid-phase incorporation of the nucleosidic building block 1 into a preselected position of an oligonucleotide sequence to give 19 is presented, a reaction performed by means of a coupling strategy involving catalytic oxazaphospholidine-ring cleavage.
Farschtschi
Nasser
N
GeneticMedizin Laboratories, Division of Biomedical Research, Bahnstrasse 2, D-97450 Arnstein. GeneticMedlabsprofdrfarsch@compuserve.com
D004164:Diphosphonates / Q000138:chemical synthesis*; D005030:Ethylenes / Q000138:chemical synthesis*; D009696:Nucleic Acids / Q000138:chemical synthesis*; D009841:Oligonucleotides / Q000138:chemical synthesis*
D004164:Diphosphonates; D005030:Ethylenes; D009696:Nucleic Acids; D009841:Oligonucleotides; C036216:ethylene