Process for preparing oligonucleotides having chiral phosphorus

Details Process for preparing oligonucleotides having chiral phosphorus Process for preparing oligonucleotides having chiral phosphorus

1993-05-05

1996-05-28

Fleisher, Mindy

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 253, 536 2533, C07H 100, C07H 2104

Patent

active

055213022

ABSTRACT:
Sequence-specific oligonucleotides are provided having substantially pure chiral Sp phosphorothioate, chiral Rp phosphorothioate, chiral Sp alkylphosphonate, 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 SN.sub.2 nucleophilic attack of a phosphodiester, phosphorothioate, phosphoramidate, phosphotriester or alkylphosphonate anion on 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.

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