Functionalized pyrimidine nucleosides and nucleotides and DNA's incorporating same

• US 6,175,001 B1
• Filed: 10/16/1998
• Issued: 01/16/2001
• Est. Priority Date: 10/16/1998
• Status: Expired due to Fees

• Current Assignee: The Scripps Research Institute
• Original Assignee: The Scripps Research Institute
• Inventors: Barbas, Carlos F., Kandasamy, Sakthiel
• Primary Examiner(s): Geist, Gary
• Assistant Examiner(s): Crane, L. Eric
• Application Number:
  US09/173,672
• Time in Patent Office: 823 Days
• Field of Search: 536/23.1, 536/26.8, 536/28.52, 536/28.55, 536/26.23, 536/26.26
• US Class Current: 536/23.1
• 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

Abstract

Modified pyrimidine nucleotides derivatized at C5 to contain a functional group that mimics the property of a naturally occurring amino acid residues are provided. DNA molecules containing the modified nucleotides are also provided.

Claims

1. A compound of the structure below

where wherein X is NH₂ or ═

O, where when X is NH₂, (H) is absent and - - - represents a chemical bond and when X is ═

O, - - - is absent and (H) is present representing a hydrogen bonded to N-1, C;

C is a carbon-carbon double bond or a carbon-carbon triple bond, each R is independently hydrogen or a metal cation or

wherein each R′

is hydrogen or a metal cation and m is 1, 2 or 3, and R₁ is

wherein R₂ is

wherein R₃ is

and n is an integer from 0 to 6.

2. The compound of claim 1 wherein n is 0, 1 or 2.

3. The compound of claim 1 wherein at least one R is a metal cation.

4. The compound of claim 3 wherein the cation is hydrogen or an alkali metal.

5. The compound of claim 4 wherein the alkali metal is sodium or potassium.

6. The compound of claim 1 where −

X is ═

O.

7. The compound of claim 1 wherein R₁ is

8. A DNA molecule comprising at least one nucleotide having the structure of the compound of claim 1.

9. A DNA molecule comprising at least one nucleotide having the structure of the compound of claim 6.

10. The DNA molecule of claim 8 that contains from about 5 to about 25 nucleotides.

11. The DNA molecule of claim 9 that contains from about 10 to about 20 nucleotides.

12. The DNA molecule of claim 9 that contains from about 5 to about 15 nucleotides.