One aspect of the present invention relates to a ribonucleoside
substituted with a phosphonamidite group at the 3'-position. In certain
embodiments, the phosphonamidite is an alkyl phosphonamidite. Another
aspect of the present invention relates to a double-stranded
oligonucleotide comprising at least one non-phosphate linkage.
Representative non-phosphate linkages include phosphonate, hydroxylamine,
hydroxylhydrazinyl, amide, and carbamate linkages. In certain
embodiments, the non-phosphate linkage is a phosphonate linkage. In
certain embodiments, a non-phosphate linkage occurs in only one strand.
In certain embodiments, a non-phosphate linkage occurs in both strands.
In certain embodiments, a ligand is bound to one of the oligonucleotide
strands comprising the double-stranded oligonucleotide. In certain
embodiments, a ligand is bound to both of the oligonucleotide strands
comprising the double-stranded oligonucleotide. In certain embodiments,
the oligonucleotide strands comprise at least one modified sugar moiety.
Another aspect of the present invention relates to a single-stranded
oligonucleotide comprising at least one non-phosphate linkage.
Representative non-phosphate linkages include phosphonate, hydroxylamine,
hydroxylhydrazinyl, amide, and carbamate linkages. In certain
embodiments, the non-phosphate linkage is a phosphonate linkage. In
certain embodiments, a ligand is bound to the oligonucleotide strand. In
certain embodiments, the oligonucleotide comprises at least one modified
sugar moiety.