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Nucleosides or nucleotides having novel unnatural bases and use thereof

外国特許コード F110005284
整理番号 E04805US
掲載日 2011年8月29日
出願国 アメリカ合衆国
出願番号 52145403
公報番号 20060263771
公報番号 7745417
出願日 平成15年2月28日(2003.2.28)
公報発行日 平成18年11月23日(2006.11.23)
公報発行日 平成22年6月29日(2010.6.29)
国際出願番号 JP2003002342
国際公開番号 WO2004007713
国際出願日 平成15年2月28日(2003.2.28)
国際公開日 平成16年1月22日(2004.1.22)
優先権データ
  • 特願2002-208568 (2002.7.17) JP
  • 2003WO-JP02342 (2003.2.28) WO
発明の名称 (英語) Nucleosides or nucleotides having novel unnatural bases and use thereof
発明の概要(英語) (US7745417)
The object of the present invention is to provide a nucleoside or nucleotide having an unnatural base.
The nucleoside or nucleotide of the present invention has a 5-substituted-2-oxo(1H)-pyridin-3-yl group as a base.
Preferably, the 5-position of the above base is substituted with a substituent selected from the group consisting of the following: 1) a photoreactive group selected from iodine and bromine; 2) an alkenyl group, an alkynyl group or an amino group, or a derivative thereof; 3) biotin or a derivative thereof; and 4) a fluorescent molecule selected from fluorescein, 6-carboxyfluorescein, tetramethyl-6-carboxyrhodamine, and derivatives thereof.
特許請求の範囲(英語) [claim1]
1. A nucleoside or nucleotide having a 5-substituted-2-oxo(1H)-pyridin-3-yl group as a base, wherein the 5-position of the base is substituted with a substituent selected from the group consisting of the following: 1) a photoreactive group selected from iodine and bromine;
2) biotin or a derivative thereof;
3) a fluorescent molecule selected from fluorescein, 6-carboxyfluorescein, and tetramethyl-6-carboxyrhodamine; and
4) an aminoalkyl linker or an aminoalkenyl linker linked to biotin, dichloroacetyl group, fluorescein, 6-carboxyfluorescein, tetramethyl-6-carboxyrhodamine, or derivatives thereof.
[claim2]
2. The nucleoside or nucleotide according to claim 1, wherein the 5-position of the base is substituted with 1) a photoreactive group selected from iodine and bromine, or 2) biotin or a derivative thereof.
[claim3]
3. The nucleoside or nucleotide according to claim 1 or 2, wherein the 5-position of the base is substituted with iodine or a biotin derivative.
[claim4]
4. A nucleic acid incorporating a nucleoside or nucleotide having a 5-substituted-2-oxo(1H)-pyridin-3-yl group as a base, wherein the 5-position of the base is substituted with a substituent selected from the group consisting of the following: 1) a photoreactive group selected from iodine and bromine;
2) biotin or a derivative thereof;
3) a fluorescent molecule selected from fluorescein, 6-carboxyfluorescein, and tetramethyl-6-carboxyrhodamine, and derivatives thereof; and
4) an aminoalkyl linker or an aminoalkenyl linker linked to biotin, dichloroacetyl group, fluorescein, 6-carboxyfluorescein, tetramethyl-6-carboxyrhodamine, or derivatives thereof.
[claim5]
5. The nucleic acid according to claim 4, wherein the nucleotide forms a base pair with a nucleotide having a 6-substituted 2-amino-purin-9-yl group as a base.
[claim6]
6. The nucleic acid according to claim 5, wherein the 6-substituted 2-amino-purin-9-yl group is a 2-amino-6-(2-thienyl)purin-9-yl group or a 2-amino-6-(dimethylamino)-purin-9-yl group.
[claim7]
7. The nucleic acid according to claim 4, which is suitable for use as antisense DNA or RNA, a ribozyme or an aptamer.
[claim8]
8. The nucleic acid according to claim 4, which encodes all or part of a protein or peptide.
[claim9]
9. A method for preparing a prepared nucleic acid comprising: effecting transcription, replication or reverse transcription by using, as a template, a template nucleic acid containing a template nucleotide having a 6-substituted 2-amino-purin-9-yl group as a base in the presence of the nucleotide according to claim 1 or 2, thereby incorporating said nucleotide as a base into said prepared nucleic acid at a site complementary to said template nucleotide having said 6-substituent 2-amino-purin-9-yl group in said template nucleic acid.
[claim10]
10. The nucleic acid according to claim 4, wherein the 5-position of the base is substituted with 1) a photoreactive group selected from iodine and bromine, or 2) biotin or a derivative thereof.
[claim11]
11. The nucleic acid according to claim 4, wherein the 5-position of the base is substituted with iodine or a biotin derivative.
[claim12]
12. The nucleoside or nucleotide according to claim 1, wherein the 5-position of the base is substituted with a substituent selected from the group consisting of: 1) a photoreactive group selected from iodine and bromine;
2) biotin;
3) a fluorescent molecule selected from fluorescein, 6-carboxyfluorescein, and tetramethyl-6-carboxyrhodamine; and
4) an aminoalkyl linker or an aminoalkenyl linker linked to biotin, dichloroacetyl group, fluorescein, 6-carboxyfluorescein, or tetramethyl-6-carboxyrhodamine.
[claim13]
13. The nucleic acid according to claim 4, wherein the 5-position of the base is substituted with a substituent selected from the group consisting of: 1) a photoreactive group selected from iodine and bromine;
2) biotin;
3) a fluorescent molecule selected from fluorescein, 6-carboxyfluorescein, and tetramethyl-6-carboxyrhodamine; and
4) an aminoalkyl linker or an aminoalkenyl linker linked to biotin, dichloroacetyl group, fluorescein, 6-carboxyfluorescein, or tetramethyl-6-carboxyrhodamine.
[claim14]
14. The method according to claim 9, wherein the 5-position of the base is substituted with a substituent selected from the group consisting of: 1) a photoreactive group selected from iodine and bromine;
2) biotin:
3) a fluorescent molecule selected from fluorescein, 6-carboxyfluorescein, and tetramethyl-6-carboxyrhodamine; and
4) an aminoalkyl linker or an aminoalkenyl linker linked to biotin, dichloroacetyl group, fluorescein, 6-carboxyfluorescein, or tetramethyl-6-carboxyrhodamine.
[claim15]
15. A nucleoside or nucleotide having a 5-substituted-2-oxo(1H)-pyridin-3-yl group as a base, represented by the formula:

wherein R1 at the 5-position is substituted with a substituent selected from the group consisting of the following: 1) a photoreactive group selected from iodine and bromine;
2) biotin, an ethylenic linker linked to biotin, an acetylenic linker linked to biotin, an aminoalkyl linker linked to biotin, and an aminoalkenyl linker linked to biotin;
3) a fluorescent molecule selected from fluorescein, 6-carboxyfluorescein and tetramethyl-6-carboxyrhodamine; and
4) an aminoalkyl linker or an aminoalkenyl linker linked to fluorescein, 6-carboxyfluorescein, or tetramethyl-6-carboxyrhodamine;
and wherein R2 is selected from the group consisting of the following: 1) a ribose or phosphorylated ribose; and
2) a deoxyribose or phosphorylated deoxyribose.
[claim16]
16. The nucleoside or nucleotide according to claim 15, wherein the 5-position of the base is substituted with 1) a photoreactive group selected from iodine and bromine or 2) biotin, an ethylenic linker linked to biotin, an acetylenic linker linked to biotin, an aminoalkyl linker linked to biotin, or an aminoalkenyl linker linked to biotin.
[claim17]
17. The nucleoside or nucleotide according to claim 15, wherein the 5-position of the base is substituted with biotin.
[claim18]
18. The nucleoside or nucleotide according to claim 15, wherein the 5-position of the base is substituted with iodine.
[claim19]
19. The nucleoside or nucleotide according to claim 15, wherein the 5-position of the base is substituted with an ethylenic linker linked to biotin or an acetylenic linker linked to biotin.
[claim20]
20. The nucleoside or nucleotide according to claim 15, wherein the nucleoside or nucleotide is selected from the group consisting of: 1) biotinylated 5-(3-amino-1-propenyl)-3-(beta -D-ribofuranosyl)-2-pyridone,
2) biotinylated 5-(3-amino-1-propen-2-yl)-3-(beta -D-ribofuranosyl)-2-pyridone,
3) biotinylated 5-(3-amino-1-propenyl)-3-(beta -D-ribofuranosyl)-2-pyridone 5'-triphosphate,
4) biotinylated 5-(3-amino-1-propen-2-yl)-3-(beta -D-ribofuranosyl)-2-pyridone 5'-triphosphate,
5) biotinylated 5-(3-amino-1-propynyl)-3-(beta -D-ribofuranosyl)-2-pyridone, and
6) biotinylated 5-(3-amino-1-propynyl)-3-(beta -D-ribofuranosyl)-2-pyridone 5'-triphosphate.
[claim21]
21. A nucleoside or nucleotide having a 5-substituted-2-oxo(1H)-pyridin-3-yl group as a base, represented by the formula:

wherein R1 at the 5-position is substituted with an ethylenic linker linked to a dichloroacetyl group or an acetylenic linker linked to a dichloroacetyl group, and wherein R2 is selected from the group consisting of the following: 1) a ribose or phosphorylated ribose; and
2) a deoxyribose or a phosphorylated deoxyribose.
[claim22]
22. A nucleic acid incorporating at least one nucleoside or nucleotide having a 5-substituted-2-oxo(1H)-pyridin-3-yl group as a base, represented by the formula:

wherein R1 at the 5-position is substituted with a substituent selected from the group consisting of the following: 1) a photoreactive group selected from iodine and bromine;
2) biotin, an aminoalkyl linker linked to biotin, or an aminoalkenyl linker linked to biotin;
3) a fluorescent molecule selected from fluorescein, 6-carboxyfluorescein and tetramethyl-6-carboxyrhodamine; and
4) an aminoalkyl linker or an aminoalkenyl linker linked to fluorescein, 6-carboxyfluorescein, or tetramethyl-6-carboxyrhodamine;
and wherein R2 is selected from the group consisting of the following: 1) a ribose or phosphorylated ribose; and
2) a deoxyribose or phosphorylated deoxyribose.
[claim23]
23. The nucleic acid according to claim 22, wherein the nucleoside or nucleotide at the 5-position of the base, is substituted with 1) a photoreactive group selected from iodine and bromine or 2) biotin, an aminoalkyl linker linked to biotin, or an aminoalkenyl linker linked to biotin.
[claim24]
24. The nucleic acid according to claim 22, wherein the 5-position of the base is substituted with biotin.
[claim25]
25. The nucleic acid according to claim 22, wherein the 5-position of the base is substituted with iodine.
[claim26]
26. The nucleic acid according to claim 22, wherein the nucleotide forms a base pair with a nucleotide having a 6-substituted 2-amino-purin-9-yl group as a base.
[claim27]
27. The nucleic acid according to claim 26, wherein the 6-substituted 2-amino-purin-9-yl group is a 2-amino-6-(2-thienyl)purin-9-yl group or a 2-amino-6-(2-dimethylamino)-purin-9-yl group.
[claim28]
28. The nucleic acid according to claim 22, wherein the nucleic acid is suitable for use as an antisense DNA or RNA, a ribozyme, or an aptamer.
[claim29]
29. The nucleic acid according to claim 22, wherein the nucleic acid encodes all or part of a protein or peptide.
[claim30]
30. A method for preparing a nucleic acid comprising: effecting transcription, replication or reverse transcription by using a template nucleic acid containing a template nucleotide having a 6-substituted 2-amino-purin-9-yl group as a base in the presence of the nucleotide according to claim 15, thereby incorporating said nucleotide as a base into said prepared nucleic acid at a site which is complementary to said template nucleotide contained in said template nucleic acid.
  • 発明者/出願人(英語)
  • HIRAO ICHIRO
  • YOKOYAMA SHIGEYUKI
  • HIRAO MICHIKO
  • MITSUI TSUNEO
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
  • RIKEN
国際特許分類(IPC)
米国特許分類/主・副
  • 514/44.000R
  • 536/22.1
  • 536/23.1
  • 536/25.3
参考情報 (研究プロジェクト等) ERATO YOKOYAMA CytoLogic AREA
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