Monomers for preparation of oligonucleotides having chiral phosphorus linkages
First Claim
1. A compound having the structure:
- ##STR10## wherein;
Q is O or CH2 ;
RD is O, S, methyl, O--C1 -C12 -alkyl, S--C1 -C12 -alkyl, amino or substituted amino, where said substituent is C1 -C12 -alkyl or C6 -C14 -aryl;
RE is O or S;
RF is H or a blocking group;
RX is H, OH, C1 -C12 -alkyl, substituted C1 -C12 -alkyl, F, Cl, Br, OCF3, O--C1 -C12 -alkyl, O-substituted C1 -C12 -alkyl, OCH2 CH═
CH2, OCH2 CCH, and C(O)--C1 -C12 -alkyl, wherein said substituent is C1 -C12 -haloalkyl, C1 -C12 -alkenyl, C1 -C12 -alkoxy, C1 -C12 -thioalkoxy, C1 -C12 -haloalkoxy, C6 -C14 -aryl, halogen, hydroxyl, amino, azido, carboxy, cyano, nitro, or mercapto;
BX is a nucleoside base or a blocked nucleoside base; and
L is a leaving group or together L and Bx are a C2 or C6 pyrimidine-3'"'"'xylo cyclo-nucleoside or C8 purine-3'"'"'xylo cyclo-nucleoside.
0 Assignments
0 Petitions
Accused Products
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 SN2 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.
-
Citations
9 Claims
-
1. A compound having the structure:
- ##STR10## wherein;
Q is O or CH2 ;RD is O, S, methyl, O--C1 -C12 -alkyl, S--C1 -C12 -alkyl, amino or substituted amino, where said substituent is C1 -C12 -alkyl or C6 -C14 -aryl; RE is O or S; RF is H or a blocking group; RX is H, OH, C1 -C12 -alkyl, substituted C1 -C12 -alkyl, F, Cl, Br, OCF3, O--C1 -C12 -alkyl, O-substituted C1 -C12 -alkyl, OCH2 CH═
CH2, OCH2 CCH, and C(O)--C1 -C12 -alkyl, wherein said substituent is C1 -C12 -haloalkyl, C1 -C12 -alkenyl, C1 -C12 -alkoxy, C1 -C12 -thioalkoxy, C1 -C12 -haloalkoxy, C6 -C14 -aryl, halogen, hydroxyl, amino, azido, carboxy, cyano, nitro, or mercapto;BX is a nucleoside base or a blocked nucleoside base; and L is a leaving group or together L and Bx are a C2 or C6 pyrimidine-3'"'"'xylo cyclo-nucleoside or C8 purine-3'"'"'xylo cyclo-nucleoside. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9)
- ##STR10## wherein;
Specification