Propargylethoxyamino nucleotides
AssigneePE Corporation (NY)
InventorsShaheer H. Khan, Steven M. Menchen, Barnett B. Rosenblum
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Abstract
Propargylethoxyamino nucleosides are disclosed having the structure 1 wherein R1 and R2 are —H, lower alkyl, or label; B is a 7-deazapurine, purine, or pyrimidine nucleoside base; W1 is —H or —OH; W2 is —OH or a moiety which renders the nucleoside incapable of forming a phosphodiester bond at the 3′-position; and W3 is —PO4, —P2O7, —P3O10, phosphate analog, or —OH. Additionaly, a primer extension method is provided employing the above propargylethoxyamino nucleosides.
Claims10
A nucleoside compound having the structure:
- 12
- wherein:
- R1 and R2 taken separately are selected from the group consisting of —H, lower alkyd protecting group, and label;
- B is a 7-deazapurine, purine, or pyrimidine nucleoside base;
- wherein when B is purine or 7-deazapurine, the sugar moiety is attached at the N9-position of the purine or deazapurine, and when B is pyrimidine, the sugar moiety is attached at the N1-position of the pyrimidine;
- and
- wherein when B is a purine, the adjacent triple-bonded carbon is attached to the 8-position of the purine, when B is 7-deazapurine, the adjacent triple-bonded carbon is attached to the 7-position of the 7-deazapurine, and when B is pyrimidine, the adjacent triple-bonded carbon is attached to the 5-position of the pyrimidine;
- W1 is selected from the group consisting of —H and —OH;
- W2 is —OH or a moiety which renders the nucleoside incapable of forming a phosphodiester bond at the 3′-position;
- and
- W3 is selected from the group consisting of —PO4, —P2O7, —P3O10, phosphate analog, and —OH.
A method for performing a primer extension reaction comprising the steps of:
- providing a template nucleic acid;
- annealing an oligonucleotide primer to a portion of the template nucleic acid;
- and
- adding primer-extension reagents to the primer-template hybrid for extending the primer, the primer extension reagents including a nucleoside compound having the structure:
- 13
- wherein:
- R1 and R2 taken separately are selected from the group consisting of —H, lower alkyl protecting group, and label;
- B is a 7-deazapurine, purine, or pyrimidine nucleoside base;
- wherein when B is purine or 7-deazapurine, the sugar moiety is attached at the N9-position of the purine or deazapurine, and when B is pyrimidine, the sugar moiety is attached at the N1-position of the pyrimidine;
- and
- wherein if B is a purine, the adjacent triple-bonded carbon is attached to the 8-position of the purine, if B is 7-deazapurine, the adjacent triple-bonded carbon is attached to the 7-position of the 7-deazapurine, and if B is pyrimidine, the adjacent triple-bonded carbon is attached to the 5-position of the pyrimidine;
- W1 is selected from the group consisting of —H and —OH;
- W2 is —OH or a moiety which renders the nucleoside incapable of forming a phosphodiester bond at the 3′-position;
- and
- W3 is selected from the group consisting of —PO4, —P2O7, —P3O10, phosphate analog, and —OH.
The method of claim 9 wherein one of R1 and R2 is label and the other is —H.
Dependencies are inferred from the claim text.