2'-O-modified nucleosides and phosphoramidites

• US 5,914,396 A
• Filed: 02/22/1995
• Issued: 06/22/1999
• Est. Priority Date: 01/11/1990
• Status: Expired due to Term

• Current Assignee: ISIS Pharmaceuticals Incorporated
• Original Assignee: ISIS Pharmaceuticals Incorporated
• Inventors: Cook, Phillip Dan, Guinosso, Charles John
• Primary Examiner(s): Kunz, Gary L.
• Application Number:
  US08/373,298
• Time in Patent Office: 1,581 Days
• Field of Search: 536/24.5, 536/24.3, 536/27.1, 536/28.1, 536/26.1, 514/44
• US Class Current: 536/26.1
• CPC Class Codes: C07H 19/06 Pyrimidine radicals
• CPC Class Codes: C07H 19/067 with ribosyl as the saccharide radical
• CPC Class Codes: C07H 19/10 with the saccharide radical esterified by phosphoric or polyphosphoric acids
• CPC Class Codes: C07H 19/16 Purine radicals
• CPC Class Codes: C07H 19/167 with ribosyl as the saccharide radical
• CPC Class Codes: C07H 19/20 with the saccharide radical esterified by phosphoric or polyphosphoric acids
• CPC Class Codes: C07H 21/00 Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
• CPC Class Codes: C07H 21/02 with ribosyl as saccharide radical
• CPC Class Codes: C07H 21/04 with deoxyribosyl as saccharide radical

Abstract

2'"'"'-O-Modified nucleosides, nucleotides, and oligonucleotides. These 2'"'"'-O-modified oligonucleotides are resistant to nuclease digestion and can effectively hybridize to a complementary polynucleotide.

Claims

1. A compound having the structure:

##STR6## wherein;

B_x is adenine, guanine, hypoxanthine, uracil, thymine, cytosine, 2-aminoadenine or 5-methylcytosine;

T₃ and T₅, independently, are OH, a nucleotide, a nucleoside, or an oligonucleotide;

X is R₁ -R₂ ;

R₁ is C₁ -C₂₀ alkyl; and

R₂ is O-alkyl, S-alkyl, NH-alkyl, N-dialkyl, O-aryl, S-aryl, NH-aryl, O-aralkyl, S-aralkyl, or NH-aralkyl.

2. The compound of claim 1 wherein R₂ is O-alkyl.

3. The compound of claim 1 wherein R₂ is NH-alkyl.

4. The compound of claim 1 wherein R₂ is N-dialkyl.