Oligodeoxyribonucleotide N3' P5' phosphoramidates
First Claim
1. An oligodeoxyribonucleotide comprising a non-homopolymeric defined sequence of nucleoside subunits joined by intersubunit linkages wherein at least fifty percent of such intersubunit linkages are N3'"'"'→
- P5'"'"' phosphoramidate linkages and wherein at least two of said N3'"'"'→
P5'"'"' phosphoramidate linkages are contiguous.
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Accused Products
Abstract
Modified oligodeoxyribonucleotide 3'"'"'--NHP (O) (O-) O-5'"'"' phosphoramidates were synthesized on a solid phase support. The phosphoramidate analogs were found to have significantly increased resistance toward phosphodiesterase digestion. Thermal dissociation experiments demonstrated that these compounds form more stable duplexes than phosphodiesters with complementary DNA and particularly RNA strands. Further, the phosphoramidate analogs can also form stable triplexes with double-stranded DNA target, where under similar conditions parent phosphodiester compounds failed to do so.
262 Citations
29 Claims
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1. An oligodeoxyribonucleotide comprising a non-homopolymeric defined sequence of nucleoside subunits joined by intersubunit linkages wherein at least fifty percent of such intersubunit linkages are N3'"'"'→
- P5'"'"' phosphoramidate linkages and wherein at least two of said N3'"'"'→
P5'"'"' phosphoramidate linkages are contiguous. - View Dependent Claims (2, 3, 4, 5, 6, 7)
- P5'"'"' phosphoramidate linkages and wherein at least two of said N3'"'"'→
-
8. An oligodeoxyribonucleotide comprising a non-homopolymeric defined sequence of nucleoside subunits joined by intersubunit linkages defined by the formula:
- ##STR1## wherein B is a purine or pyrimidine or an analog thereof; and
n is between 2 and 48, inclusive. - View Dependent Claims (9, 10)
- ##STR1## wherein B is a purine or pyrimidine or an analog thereof; and
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11. An oligodeoxyribonucleotide comprising a non-homopolymeric defined sequence of the following formula:
- ##STR2## wherein B is a purine or pyrimidine or an analog thereof;
n is at least 3; and
X is O-, methyl, or methoxy, and wherein said oligodeoxyribonucleotide has at least fifty percent N3'"'"'→
P5'"'"' phosphoramidate linkages. - View Dependent Claims (12, 13, 21, 22, 23, 24)
- ##STR2## wherein B is a purine or pyrimidine or an analog thereof;
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14. An oligodeoxyribonucleotide comprising a defined sequence of nucleoside subunits joined by intersubunit linkages wherein the oligodeoxyribonucleotide is capable of forming a hairpin oligomer consisting of a duplex region and a loop region, and wherein at least fifty percent of the intersubunit linkages in the duplex region of the hairpin oligomer are N3'"'"'→
- P5'"'"' phosphoramidate linkages.
- View Dependent Claims (15, 16, 17, 18, 19, 20)
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25. A non-homopolymeric oligodeoxyribonucleotide comprising a defined sequence of nucleoside subunits joined by intersubunit linkages wherein:
- (i) at least fifty percent of such intersubunit linkages are N3'"'"'→
P5'"'"' phosphoramidate linkages, (ii) at least two of said N3'"'"'→
P5'"'"' phosphoramidate linkages are contiguous, and (iii) the oligodeoxyribonucleotide has at least three intersubunit linkages. - View Dependent Claims (26, 27, 28, 29)
- (i) at least fifty percent of such intersubunit linkages are N3'"'"'→
Specification