2' Modified Oligonucleotides
AssigneeGilead Sciences, Inc.
InventorsChris A. Buhr, Mark Matteucci
Life of this patent
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Abstract
Oligomers which have substituents on the 2' position are resistant to oligonucleases and furthermore can be derivatized to deliver reagents or drugs, to carry label, or to provide other properties.
Claims35
An oligonucleotide having the formula ##STR6## or a salt thereof, wherein each B is independently a protected or unprotected purine or pyrimidine base in the .beta.-anomeric configuration;
- W.sub.3 and W.sub.4 are each independently H, PO.sub.3.sup.-2, a protecting group, or an intermediate moiety in the formation of an internucleotide link which when reacted with the appropriate --OH results in Z;
- each Z independently is P(O)O, P(O)S or P(O)N(R).sub.2 ;
- each R is independently H or alkyl (1-6 C);
- n is an integer of 1-200;
- each A is independently selected from the group consisting of --X--Y, H, OH or --OPr wherein Pr is a protecting group wherein
- X is O;
- Y is substituted alkyl (2-20 C) or substituted or unsubstituted alkenyl (2-20 C), wherein the substituents are a halogen, OH, NH.sub.2, SH, --O--, --CH.sub.2 CONH.sub.2, --CH.sub.2 COOCH.sub.2 CH.sub.3 or --CH.sub.2 CONHCH.sub.2 CH.sub.2 NH.sub.2 ;
- and
- wherein at least one A is X--Y.
An oligonucleotide having the formula ##STR7## or a salt thereof, wherein each B is independently a protected or unprotected purine or pyrimidine base in the .beta.-anomeric configuration;
- W.sub.3 and W.sub.4 are each independently H, PO.sub.3.sup.-2, a protecting group, or an intermediate moiety in the formation of an internucleotide link which when reacted with the appropriate --OH results in Z;
- each Z independently is --P(O)O--, --P(O)S-- or --P(O)N(R).sub.2 --;
- each R is independently H or alkyl (1-6 C);
- n is an integer of 1-200;
- each A is independently selected from the group consisting of --X--Y, --H, --OH or --OPr wherein Pr is a protecting group, wherein
- X is --CH.sub.2 --, --S-- or --NH--;
- Y is substituted alkyl (2-20 C) or substituted or unsubstituted alkenyl (2-20 C), wherein the substituents are a halogen, --OH, --NH.sub.2, --SH, --O--, --CH.sub.2 CONH.sub.2, --CH.sub.2 COOCH.sub.2 CH.sub.3 or --CH.sub.2 CONHCH.sub.2 CH.sub.2 NH.sub.2 ;
- and
- wherein at least one A is --X--Y.
An oligonucleotide having the formula ##STR8## or a salt thereof, wherein each B is independently a protected or unprotected purine or pyrimidine base in the .beta.anomeric configuration;
- W.sub.3 and W.sub.4 are each independently H, PO.sub.3.sup.-2, a protecting group, or an intermediate moiety in the formation of an internucleotide link which when reacted with the appropriate --OH results in Z;
- each Z independently is --P(O)O--, --P(O)S-- or --P(O)N(R).sub.2 --;
- each R is independently --H or alkyl (1-6 C);
- n is an integer of 1-200;
- each A is independently selected from the group consisting of --X--Y, --H, --OH or --OPr wherein Pr is a protecting group wherein
- X is --O--;
- Y is substituted alkyl (2-20 C) or substituted or unsubstituted alkenyl (2-20 C), wherein the substituents are a halogen, --OH, --NH.sub.2, --SH, --O--, --COOH, --C(O)--, --CH.sub.2 COOH, --CH.sub.2 CONH.sub.2, --CH.sub.2 COOCH.sub.2 CH.sub.3 or --CH.sub.2 CONHCH.sub.2 CH.sub.2 NH.sub.2 ;
- and
- wherein at least one A is --X--Y.
Dependencies are inferred from the claim text.