Nucleotide monomers containing 8-azapurin bases or a derivative thereof, their preparation and their use in making modified olignonucleotides
First Claim
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1. A nucleotide monomer of the formula V ##STR19## in which V is oxy, sulfanediyl or imino;
- Yb is oxy, sulfanediyl, or methylene;
a is oxy or methylene;
R2b is hydrogen, OR12, C1 -C18 -alkoxy, C1 -C6 -alkenyloxy, halogen, azido or NR10 R11 ;
R1 is a protective group which is customary in nucleotide chemistry;
R1b is a radical of the formula IIc or IId ##STR20## in which U is O--R7 or S--R7 ;
Q is a radical --NR8 R9 ;
R7 is --(CH2)2 --CN;
R8 and R9 are identical or different and are C1 -C6 -alkyl, or, together with the nitrogen atom carrying them, are a 5-9-membered heterocyclic ring which can additionally contain a further heteroatom selected from the group O, S, and N,E'"'"' and F'"'"' are, independently of each other, H, OH, or NR10 R11,R10 and R11 are identical or different and are hydrogen or an amino protective group which is customary in nucleotide chemistry, or R10 and R11 together form an amino protective group which is customary in nucleotide chemistry,R12 is a hydroxyl protective group which is customary in nucleotide chemistry,and the curved bracket indicates that R2b and the adjacent phosphoryl radical can be in the 2'"'"' and 3'"'"' positions, or else, conversely, in the 3'"'"' and 2'"'"' positions.
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Abstract
The invention relates to novel modified oligonucleotides which contain at least one 8-azapurine base and form more stable hybridization complexes with nucleic acids; To a process for their preparation, and to their use as inhibitors of gene expression, as probes for detecting nucleic acids, as aids in molecular biology, and as a pharmaceutical or diagnostic agent.
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Citations
6 Claims
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1. A nucleotide monomer of the formula V ##STR19## in which V is oxy, sulfanediyl or imino;
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Yb is oxy, sulfanediyl, or methylene; a is oxy or methylene; R2b is hydrogen, OR12, C1 -C18 -alkoxy, C1 -C6 -alkenyloxy, halogen, azido or NR10 R11 ; R1 is a protective group which is customary in nucleotide chemistry; R1b is a radical of the formula IIc or IId ##STR20## in which U is O--R7 or S--R7 ; Q is a radical --NR8 R9 ; R7 is --(CH2)2 --CN; R8 and R9 are identical or different and are C1 -C6 -alkyl, or, together with the nitrogen atom carrying them, are a 5-9-membered heterocyclic ring which can additionally contain a further heteroatom selected from the group O, S, and N, E'"'"' and F'"'"' are, independently of each other, H, OH, or NR10 R11, R10 and R11 are identical or different and are hydrogen or an amino protective group which is customary in nucleotide chemistry, or R10 and R11 together form an amino protective group which is customary in nucleotide chemistry, R12 is a hydroxyl protective group which is customary in nucleotide chemistry, and the curved bracket indicates that R2b and the adjacent phosphoryl radical can be in the 2'"'"' and 3'"'"' positions, or else, conversely, in the 3'"'"' and 2'"'"' positions. - View Dependent Claims (2, 3, 5, 6)
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4. A compound of the formula VI ##STR21## in which, independently of each other, U'"'"'=U"=U"'"'"' is hydroxyl or mercapto;
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e and f are 0 or 1; R13 is hydrogen or OH, and E and F are H, OH or NH2, excluding compounds of the formula VI in which U'"'"', U", U"'"'"', R13 and F are OH, E is NH2, and e and f are 1.
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Specification