Triphosphate oligonucleotide modification reagents and uses thereof

• US 6,686,461 B1
• Filed: 08/01/2000
• Issued: 02/03/2004
• Est. Priority Date: 03/22/2000
• Status: Expired due to Term

• Current Assignee: Vector Laboratories
• Original Assignee: Solulink Biosciences Incorporated
• Inventors: Schwartz, David A., Hogrefe, Richard I.
• Primary Examiner(s): Wilson, James O.
• Assistant Examiner(s): LEWIS, PATRICK T
• Application Number:
  US09/630,627
• Time in Patent Office: 1,281 Days
• Field of Search: 536/26.26, 536/25.3, 536/25.32, 536/22.1
• US Class Current: 536/26.26
• CPC Class Codes: C07H 19/00 Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
• CPC Class Codes: C07H 19/04 Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
• 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 21/04 with deoxyribosyl as saccharide radical

Abstract

Hydrazino, oxyamino and carbonyl-based monomers and methods for incorporation into oligonucleotides during enzymatic synthesis are provided. Modified oligonucleotides are provided that incorporate the monomers provided herein. Immobilized oligonucleotides and oligonucleotide conjugates that contain covalent hydrazone or oxime linkages are provided. Methods for preparation of surface bound oligonucleotides are provided. Methods for the preparation of oligonucleotide conjugates are also provided.

Claims

1. A compound that has formula (I) or salt thereof:

2. The compound of claim 1, that has the formula:

3. The compound of claim 1, that has the formula:

wherein R is H or OH.

4. The compound of claim 1, that has the formula:

wherein R is H or OH.

5. The compound of claim 1, wherein X is a protected hydrazino group.

6. The compound of claim 5, wherein the protecting group is a salt.

7. The compound of claim 1, wherein X is a carbonyl group.

8. The compound of claim 1, wherein X is an aldehyde or ketone group.

9. The compound of claim 1, wherein X is a protected oxyamino group.