Biotin containing C-glycoside nucleic acid labeling compounds
View Patent ↗Nucleic acid labeling compounds including the following structure are disclosed: wherein A is a triphosphate group with apporpriate counterions, said counterions selected from the group consisting of H+, Na+, Li+, K+, and NH 4 +; X is O; Y is OH; Z is OH; L is selected from the group consisting of —CH═CH—C(O)—NH—CH 2 —CH 2 —NH—C(O)— and —CH 2 —CH 2 —C(O)—NH—CH 2 —CH 2 —NH—C(O); M is —(CH 2 ) 45 —NH—, n is 1 and Q is biotin having the structure: The labeling compounds are suitable for enzymatic attachment to a nucleic acid, either terminally or internally, to provide a mechanism of nucleic acid detection.
1. A nucleic acid labeling compound of the following structure:
wherein A is a triphosphate group with apporpriate counterions, said counterions selected from the group consisting of H+, Na+, Li+, K+, and NH 4 +; X is O; Y is OH; Z is OH; L is selected from the group consisting of —CH═CH—C(O)—NH—CH 2 —CH 2 —NH—C(O)— and —CH 2 —CH 2 —C(O)—NH—CH 2 —CH 2 —NH—C(O); M is —(CH 2 ) 45 —NH—, n is 1 and Q is biotin having the structure:
2. A nucleic acid labeling compound according to claim 1 wherein L is —CH═CH—C(O)—NH—CH 2 —CH 2 —NH—C(O)—.
3. A nucleic acid derivative produced by coupling a nucleic acid labeling compound according to claim 1 with a nucleic acid.
4. A hybridization product, wherein the hybridization product comprises the nucleic acid derivative according to claim 3 bound to a complementary probe.
5. The hybridization product according to claim 4 , wherein the probe is attached to a glass chip.
6. A method of synthesizing a labeled nucleic acid comprising attaching a nucleic acid labeling compound according to claim 1 to a nucleic acid.
7. A method of detecting a nucleic acid comprising incubating a nucleic acid derivative according to claim 3 with a probe.
8. A method according to claim 7 , wherein the probe is attached to a glass chip.
9. A nucleic acid labeling compound of the following structure:
wherein A is a triphosphate group with apporpriate counterions, said counterions selected from the group consisting of H+, Na+, Li+, K+, and NH 4 +; X is O; Y is OH; Z is OH; L is selected from the group consisting of —CH═CH—C(O)—NH—CH 2 —CH 2 —NH—C(O)— and —CH 2 —CH 2 —C(O)—NH—CH 2 —CH 2 —NH—C(O); M is —(CH 2 ) 45 —NH—, n is 1 and Q is biotin having the structure:
10. A nucleic acid labeling compound according to claim 9 wherein L is —CH═CH—C(O)—NH—CH 2 —CH 2 —NH—C(O)—.
11. A nucleic acid derivative produced by coupling a nucleic acid labeling compound according to claim 9 with a nucleic acid.
12. A hybridization product, wherein the hybridization product comprises the nucleic acid derivative according to claim 11 bound to a complementary probe.
13. The hybridization product according to claim 12 , wherein the probe is attached to a glass chip.
14. A method of synthesizing a labeled nucleic acid comprising attaching a nucleic acid labeling compound according to claim 9 to a nucleic acid.
15. A method of detecting a nucleic acid comprising incubating a nucleic acid derivative according to claim 11 with a probe.
16. A method according to claim 15 , wherein the probe is attached to a glass chip.
17. A nucleic acid labeling compound having the structure
wherein A is a triphosphate group with apporpriate counterions, said counterions selected from the group consisting of H+, Na+, Li+, K+, and NH 4 +, Y is OH; Z is OH; L is —C(O)NH(CH 2 ) 2 NH—, M is selected from the group consisting of —C(O)(CH2) 5 NH— and —C(O)((CH 2 ) 2 O) 4 (CH 2 ) 2 NH—, n is 1 and Q is biotin, having the structure:
18. A nucleic acid labeling compound according to claim 17 wherein M is —C(O)(CH2) 5 NH—.
19. A nucleic acid derivative produced by coupling a nucleic acid labeling compound according to claim 17 with a nucleic acid.
20. A hybridization product, wherein the hybridization product comprises the nucleic acid derivative according to claim 19 bound to a complementary probe.
21. The hybridization product according to claim 20 , wherein the probe is attached to a glass chip.
22. A hybridization product, wherein the hybridization product comprises the nucleic acid derivative according to claim 18 bound to a complementary probe.
23. The hybridization product according to claim 22 , wherein the probe is attached to a glass chip.
24. A method of synthesizing a labeled nucleic acid comprising attaching a nucleic acid labeling compound according to claim 17 to a nucleic acid.
25. A method of detecting a nucleic acid comprising incubating a nucleic acid derivative according to claim 19 with a probe.
26. A method according to claim 25 , wherein the probe is attached to a glass chip.