Oligonucleotides having chiral phosphorus linkages

Details Oligonucleotides having chiral phosphorus linkages Oligonucleotides having chiral phosphorus linkages

C - Chemistry, Metallurgy

12

N

C12N 15/10 (2006.01) A61K 31/70 (2006.01) A61K 48/00 (2006.01) C07H 19/04 (2006.01) C07H 19/10 (2006.01) C07H 19/20 (2006.01) C07H 21/00 (2006.01) C07H 23/00 (2006.01) C12N 5/10 (2006.01) C12N 15/11 (2006.01) C12P 19/34 (2006.01) C12Q 1/68 (2006.01) C12Q 1/70 (2006.01)

Patent

CA 2121144

Sequence-specific oligonucleotides are provided having substantially pure chiral Sp phosphorothioate, chiral Rp phosphorothioate, chiral Sp alkylphosphociate, chiral Rp alkylphosphonate, chiral Sp phosphoamidate, chiral Rp phosphoamidate, chiral Sp phosphotriester, and chiral Rp phosphotriester linkages. The novel oligonucleotides are prepared via a stereospecific SN2 nucleophilic attack of a phosphodiester, phosphorothioate, phosphoramidate, phosphotriester, or alkyl- phosphate anion on the the 3' position of a xylonucleotide. The reaction proceeds via inversion at the 3' position of the xylo reactant species, resulting in the incorporation of phosphodiester, phosphorothioate, phosphoramidate, phosphotriester, or alkylphosphonate linked ribofuranosyl sugar moieties into the oligonucleotide. Alternatively, enzymatic methods are used to prepare oligonucleotides having chirally pure phosphorus inter-sugar linkages. Therapeutic and diagnostic methods using the same are also provided.

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