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US 6,320,035 B1Granted
C-nucleoside derivatives and their use in the detection of nucleic acids
AssigneeRoche Diagnostics GmbH
InventorsKlaus Mühlegger, Herbert Von Der Eltz, Frank Seela, Helmet Rosemeyer
Life of this patent
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Abstract
The invention concerns pyrrolo-[3,2-d]pyrimidine, pyrazolo-[4,3-d]pyrimidine and pyrimidine-furanosides i.e. so-called C-nucleosides of the general formulae I-V or appropriate derivatives as well as processes for their production.
Claims50
An oligonucleotide, synthesized from nucleosides, wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)nNH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a reporter group,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkynyl, a protecting group and a reporter group,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a reporter group which is bound to the pyrimidine or furanose ring via a linker group, wherein the linker group contains an alkynyl group.
5 more elements
An oligonucleotide, synthesized from nucleosides, wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a reporter group,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkynyl, a protecting group and a reporter group,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a reporter group which is bound to the pyrimidine or furanose ring via a linker group, wherein the linker group contains an ethylene glycol group.
5 more elements
An oligonucleotide, synthesized from nucleosides, wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a reporter group,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkynyl, a protecting group and a reporter group,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a reporter group which is bound to the pyrimidine or furanose ring via a linker group.
5 more elements
An oligonucleotide, synthesized from nucleosides, wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkinyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a reporter group,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkinyl, a protecting group and a reporter group,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a reporter group which is bound to the pyrimidine or furanose ring via a linker group, wherein the linker group contains an alkynyl group and is of a sufficient length such that the compound can be incorporated into the oligonucleotide by means of a polymerase.
5 more elements
An oligonucleotide, synthesized from nucleosides, wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkinyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a reporter group,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkinyl, a protecting group and a reporter group,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a reporter group which is bound to the pyrimidine or furanose ring via a linker group, wherein the linker group contains an ethylene glycol group and is of a sufficient length such that the compound can be incorporated into the oligonucleotide by means of a polymerase.
5 more elements
A nucleic acid, synthesized from nucleosides, wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, C≡C—(CH2)n—NH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a reporter group,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡—C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkynyl, a protecting group and a reporter group,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, (CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a reporter group which is bound to the pyrimidine or furanose ring via a linker group, wherein the linker group contains an alkynyl group.
5 more elements
A nucleic acid, synthesized from nucleosides, wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a reporter group,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkynyl, a protecting group and a reporter group,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a reporter group which is bound to the pyrimidine or furanose ring via a linker group, wherein the linker group contains an ethylene glycol group.
5 more elements
A nucleic acid, synthesized from nucleosides, wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a reporter group,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 —O—C2-C6 alkynyl, a protecting group and a reporter group,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a reporter group which is bound to the pyrimidine or furanose ring via a linker group.
5 more elements
A nucleic acid, synthesized from nucleosides, wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkenyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a reporter group,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkinyl, a protecting group and a reporter group,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a reporter group which is bound to the pyrimidine or furanose ring via a linker group, wherein the linker group contains an alkynyl group and is of a sufficient length such that the compound can be incorporated into the nucleic acid by means of a polymerase.
5 more elements
A nucleic acid, synthesized from nucleosides, wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkinyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a reporter group,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkinyl, a protecting group and a reporter group,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=1-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a reporter group which is bound to the pyrimidine or furanose ring via a linker group, wherein the linker group contains an ethylene glycol group and is of a sufficient length such that the compound can be incorporated into the nucleic acid by means of a polymerase.
5 more elements
A method for detecting nucleic acids, comprising
- (a) hybridizing a nucleic acid to be detected with a labeled probe, wherein said probe is synthesized from nucleosides, wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a label,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 —O—C2-C6 alkynyl, a protecting group and a label,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a label which is bound to the pyrimidine or furanose ring via a linker group, wherein the linker group contains an alkynyl group, and
- (b) detecting said labeled probe as an indication of the presence of said nucleic acid to be detected.
7 more elements
A method for detecting nucleic acids, comprising
- (a) hybridizing a nucleic acid to be detected with a labeled probe, wherein said probe is synthesized from nucleosides, wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)nNH2 wherein n=1-15, —(CH2)—C(═O)—NH2 wherein n=1-5, —NH—(CH2)nCH3 wherein n=0-5, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)nNH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a label,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10 , —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)nNH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkynyl, a protecting group and a label,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)n—CH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a label which is bound to the pyrimidine or furanose ring via a linker group, wherein the linker group contains an ethylene glycol group, and
- (b) detecting said labeled probe as an indication of the presence of said nucleic acid to be detected.
7 more elements
A method for detecting nucleic acids, comprising
- (a) hybridizing a nucleic acid to be detected with a labeled probe, wherein said probe is synthesized from nucleosides, wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a label,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)nNH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkynyl, a protecting group and a label,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a label which is bound to the pyrimidine or furanose ring via a linker group, and
- (b) detecting said labeled probe as an indication of the presence of said nucleic acid to be detected.
7 more elements
A method for detecting nucleic acids, comprising
- (a) hybridizing a nucleic acid to be detected with a labeled probe, wherein said probe is synthesized from nucleosides, wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)nNH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C═C—(CH2)nNH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a label,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkynyl, a protecting group and a label,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a label which is bound to the pyrimidine or furanose ring via a linker group, wherein the linker group contains an alkynyl group and is of a sufficient length such that the compound can be incorporated into the probe by means of a polymerase, and
- (b) detecting said labeled probe as an indication of the presence of said nucleic acid to be detected.
7 more elements
A method for detecting nucleic acids, comprising
- (a) hybridizing a nucleic acid to be detected with a labeled probe, wherein said probe is synthesized from nucleosides, wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a label,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)nNH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkynyl, a protecting group and a label,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a label which is bound to the pyrimidine or furanose ring via a linker group, wherein the linker group contains an ethylene glycol group and is of a sufficient length such that the compound can be incorporated into the probe by means of a polymerase, and
- (b) detecting said labeled probe as an indication of the presence of said nucleic acid to be detected.
7 more elements
A method for chemically synthesizing an oligonucleotide, comprising synthesizing an oligonucleotide chain on a solid support by stepwise linking nucleosides, and cleaving said oligonucleotide chain from said solid carrier,
- wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a reporter group,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkynyl, a protecting group and a reporter group,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a reporter group which is bound to the pyrimidine or furanose ring via a linker group, wherein the linker group contains an alkynyl group.
6 more elements
A method for chemically synthesizing an oligonucleotide, comprising synthesizing an oligonucleotide chain on a solid support by stepwise linking nucleosides, and cleaving said oligonucleotide chain from said solid carrier,
- wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C═C—(CH2)n—NH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a reporter group,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=1-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkynyl, a protecting group and a reporter group,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a reporter group which is bound to the pyrimidine or furanose ring via a linker group, wherein the linker group contains an ethylene glycol group.
6 more elements
A method for chemically synthesizing an oligonucleotide, comprising synthesizing an oligonucleotide chain on a solid support by stepwise linking nucleosides, and cleaving said oligonucleotide chain from said solid carrier,
- wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C6H5—, —O—(CH2)n—CH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a reporter group,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkynyl, a protecting group and a reporter group,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a reporter group which is bound to the pyrimidine or furanose ring via a linker group.
6 more elements
A method for chemically synthesizing an oligonucleotide, comprising synthesizing an oligonucleotide chain on a solid support by stepwise linking nucleosides, and cleaving said oligonucleotide chain from said solid carrier,
- wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkinyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a reporter group,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)nNH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkinyl, a protecting group and a reporter group,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a reporter group which is bound to the pyrimidine or furanose ring via a linker group, wherein the linker group contains an alkynyl group and is of a sufficient length such that the compound can be incorporated into the oligonucleotide by means of a polymerase.
6 more elements
A method for chemically synthesizing an oligonucleotide, comprising synthesizing an oligonucleotide chain on a solid support by stepwise linking nucleosides, and cleaving said oligonucleotide chain from said solid carrier,
- wherein at least one of the nucleosides is a compound of formula V:
- wherein
- R1, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, carboxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkinyl, C6H5—, —O—(CH2)nCH3 wherein n=0-6, —O—C6H5, —(CH2)nC6H5 wherein n=1-6, —O—(CH2)nC6H5 wherein n=1-6, and a reporter group,
- R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, amino, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)n—NH2 wherein n=1-15, —CH═(CH2)nNH2 wherein n=1-6, —C≡C—(CH2)n—NH2 wherein n=1-10, —O—(CH2)nCH3 wherein n=0-6, —O—C2-C6 alkenyl, —O—C2-C6 alkinyl, a protecting group and a reporter group,
- R7 is a phosphoramidite or H-phosphonate group,
- R8 is selected from the group consisting of hydrogen or a hydroxy, thio, —(CH2)n—SH wherein n=1-10, —S—(CH2)nCH3 wherein n=0-10, an amino group, —(CH2)n—NH2 wherein n=1-15, —(CH2)nC(═O)—NH2 wherein n=1-15, —NH—(CH2)nCH3 wherein n=0-15, —NH—(CH2)nNH2 wherein n=1-15, —CH═(CH2)n—NH2 wherein n=1-6, and —C≡C—(CH2)n—NH2 wherein n=1-10, and
- R9 is a protecting group,
- or a tautomer or salt thereof,
- wherein at least one of R1, R2, R3, R5 and R6 is a reporter group which is bound to the pyrimidine or furanose ring via a linker group, wherein the linker group contains an ethylene glycol group and is of a sufficient length such that the compound can be incorporated into the oligonucleotide by means of a polymerase.
6 more elements
Dependencies are inferred from the claim text.